title: Fop

text: In Thomas Mann's 1912 novella "Death in Venice" (as well as the opera by Benjamin Britten and the film by Luchino Visconti) a fop is derided by the main character, Gustave von Aschenbach; ironically so, as Aschenbach ultimately dresses in this manner himself. Some of the "bright young things" of the 1920s were decidedly "foppish" in manner and appearance, while, towards the late 1960s, male fashion became notably foppish in style, evocative loosely of the Georgian and Victorian eras. Pop stars often dressed in what might be termed foppish clothing, with the Kinks' song "Dedicated Follower of Fashion" (1966) capturing well the spirit of the time. While many characters from popular culture had a tendency to foppish appearance, "e.g.", "Adam Adamant Lives!", the third incarnation of Doctor Who and "Jason King", they tended not to exhibit mannerisms associated with fops. In Mel Brooks' "History of the World, Part I", in the French Revolution sequence, one of the king's court is referred to as "Popinjay".


title: Fop

text: The British Fops, or Lucien Callow (Mark McKinney) and Fagan (David Koechner), appeared in several episodes during the "Saturday Night Live" 1995–1996 seasons. The characters first appeared on Weekend Update as the presidents of the Norm Macdonald fan-club, but later appeared in several other sketches, namely monologues. The Fops would appear in late Restoration period clothing and used a silly take on the period's language, mannerisms, culture, and sexual attitudes.


title: Fop

text: Early examples of the fop in media of the twenty-first century include the hair-obsessed Ulysses Everett McGill (played by George Clooney) in the Coen brothers film "O Brother Where Art Thou" (2001) and the character of Jack Sparrow (played by Johnny Depp) in the "Pirates of the Caribbean" film series. Depp's style has been termed "grunge fop". The actor's mannerisms caused concerns among executives at the Walt Disney Company but prevailed, thereby creating a new generation of fans of the fop.


title: Fop

text: In popular series "Blackadder the Third", Hugh Laurie portrayed George, Prince Regent as a distinctly childish fop in contrast to his shrewd and sarcastic butler E. Blackadder (played by Rowan Atkinson).


title: Fop

text: In Channel 4's "Vic Reeves Big Night Out", character Graham Lister regularly refers to Reeves as "the Fop". In Quentin Tarantino's 2012 slavery epic "Django Unchained", Jamie Foxx's title character, when allowed to choose his own clothing for the first time in his life, chose a decidedly foppish outfit which immediately earned him the nickname "Fancypants".


title: Fop

text: In the 2007 video game "", Detective Ema Skye constantly refers to the prosecutor Klavier Gavin as a "glimmerous fop" due to the bling that he would typically wear and his obsession with his appearance. The term fop is also used occasionally to refer to other characters, particularly being picked up by Apollo Justice due to the detective's habit of saying it.


title: Fop

text: Other examples include Patrick Bateman, the protagonist of the novel "American Psycho", and the clothes-obsessed Prince Kai in the book "Firebood" by Elly Blake (2017).


title: Fop

text: A more recent and minor trend is "fop rock", a form of camp in which the performers don 18th-century wigs, lace cravats, and similar costume elements to perform. The style appears to owe something to glam rock, visual kei, and the New Romantic movement. The look was pioneered in the 1960s by Paul Revere & the Raiders. Adam Ant of Adam and the Ants picked up the trend, occasionally performing in elaborate highwayman outfits. Other notable examples would be Falco's performance as Wolfgang Amadeus Mozart in the song "Rock Me Amadeus" (a No. 1 hit in the US, the UK and Canada in 1986), Japanese rock group Malice Mizer, and Boston-based band the Upper Crust. Mid-2000s glam rock revivalists White Hot Odyssey also affected 18th century-style wigs and clothing for their live performances. Prince was known for his foppish clothing in the mid-1980s, with ruffled shirts, tight pants and high-heeled boots.


title: Bicalutamide

text: Bicalutamide, sold under the brand name Casodex among others, is an antiandrogen medication that is primarily used to treat prostate cancer. It is typically used together with a gonadotropin-releasing hormone (GnRH) analogue or surgical removal of the testicles to treat advanced prostate cancer. To a lesser extent, it is used for early prostate cancer at a higher dosage as a monotherapy without castration. Bicalutamide is also used to treat excessive hair growth and scalp hair loss in women, as a component of feminizing hormone therapy for transgender women, to treat early puberty in boys, and to prevent overly long-lasting erections in men. It is taken by mouth.


title: Bicalutamide

text: Common side effects in men include breast enlargement, breast tenderness, and hot flashes. Other side effects in men include feminization and sexual dysfunction. Some side effects like breast changes and feminization are minimal when combined with castration. While the medication appears to produce few side effects in women, its use in cisgender women is not explicitly approved by the Food and Drug Administration (FDA) at this time. Use during pregnancy may harm the baby. Bicalutamide causes abnormal liver changes necessitating discontinuation in around 1% of people. Rarely, it has been associated with cases of liver damage, lung toxicity, and sensitivity to light. Although the risk of adverse liver changes is small, monitoring of liver function is recommended during treatment.


title: Bicalutamide

text: Bicalutamide is a member of the nonsteroidal antiandrogen (NSAA) group of medications. It works by selectively blocking the androgen receptor (AR), the biological target of the androgen sex hormones testosterone and dihydrotestosterone (DHT). It does not lower androgen levels. The medication can have some estrogen-like effects in men when used as a monotherapy due to increased estradiol levels. Bicalutamide is well-absorbed, and its absorption is not affected by food. The elimination half-life of the medication is around one week. It shows peripheral selectivity in animals, but crosses the blood–brain barrier and affects both the body and brain in humans.


title: Bicalutamide

text: Bicalutamide was patented in 1982 and approved for medical use in 1995. It is on the World Health Organization's List of Essential Medicines. Bicalutamide is available as a generic medication. The drug is sold in more than 80 countries, including most developed countries. It is the most widely used antiandrogen in the treatment of prostate cancer, and has been prescribed to millions of men with the disease.


title: Bicalutamide

text: In Japan, bicalutamide is uniquely used at a dosage of 80 mg/day both in combination with castration and as a monotherapy in the treatment of prostate cancer.


title: Bicalutamide

text: Bicalutamide is available for the treatment of prostate cancer in most developed countries, including over 80 countries worldwide. It is available in 50 mg, 80 mg (in Japan), and 150 mg tablets for oral administration. The drug is registered for use as a 150 mg/day monotherapy for the treatment of in at least 55 countries, with the being a notable exception where it is registered only for use at a dosage of 50 mg/day in combination with castration. No other formulations or routes of administration are available or used. All formulations of bicalutamide are specifically indicated for the treatment of prostate cancer alone or in combination with surgical or medication castration. A combined formulation of bicalutamide and the agonist goserelin in which goserelin is provided as a subcutaneous implant for injection and bicalutamide is included as 50 mg tablets for oral ingestion is marketed in Australia and New Zealand under the brand name ZolaCos CP (Zoladex–Cosudex Combination Pack).


title: Bicalutamide

text: Bicalutamide is pregnancy category X, or "contraindicated in pregnancy", in the , and pregnancy category D, the second most restricted rating, in Australia. As such, it is contraindicated in women during pregnancy, and women who are sexually active and who can or may become pregnant are strongly recommended to take bicalutamide only in combination with adequate contraception. It is unknown whether bicalutamide is excreted in breast milk, but many drugs are excreted in breast milk, and for this reason, bicalutamide treatment is similarly not recommended while breastfeeding.


title: Bicalutamide

text: In individuals with severe, though not mild-to-moderate hepatic impairment, there is evidence that the elimination of bicalutamide is slowed, and hence, caution may be warranted in these patients as circulating levels of bicalutamide may be increased. In severe hepatic impairment, the elimination half-life of the active ("R")-enantiomer of bicalutamide is increased by about 1.75-fold (76% increase; elimination half-life of 5.9 and 10.4 days for normal and impaired patients, respectively). The elimination half-life of bicalutamide is unchanged in renal impairment.


title: Bicalutamide

text: The side effect profile of bicalutamide is highly dependent on sex; that is, on whether the person is male or female. In men, due to androgen deprivation, a variety of side effects of varying severity may occur during bicalutamide treatment, with breast pain/tenderness and gynecomastia (breast development/enlargement) being the most common. Gynecomastia occurs in up to 80% of men treated with bicalutamide monotherapy, though is of only mild-to-moderate severity in more than 90% of affected men. In addition to breast changes, physical feminization and demasculinization in general, including reduced body hair growth, decreased muscle mass and strength, feminine changes in fat mass and distribution, reduced penile length, and decreased semen/ejaculate volume, may occur in men. Other side effects that have been observed in men and that are similarly related to androgen deprivation include hot flashes, sexual dysfunction (e.g., loss of libido, erectile dysfunction), depression, fatigue, weakness, and anemia. However, most men have preserved sexual function with bicalutamide monotherapy. In females, due to the minimal biological importance of androgens in this sex, the side effects of pure antiandrogens or are few, and bicalutamide has been found to be very well tolerated. General side effects of bicalutamide that may occur in either sex include diarrhea, constipation, abdominal pain, nausea, dry skin, itching, and rash. The drug is well-tolerated at higher dosages than 50 mg/day, with rare additional side effects.


title: Bicalutamide

text: Bicalutamide has been associated with abnormal liver function tests such as elevated liver enzymes. In the Early Prostate Cancer (EPC) clinical programme of bicalutamide for early prostate cancer, the rate of abnormal liver function tests with bicalutamide monotherapy was 3.4% relative to 1.9% for placebo. Hepatic changes that have necessitated discontinuation of bicalutamide, such as marked increases in liver enzymes or hepatitis, have occurred in approximately 0.3 to 1.4% of men in clinical trials. Elevated liver enzymes with bicalutamide usually occur within the first 3 to 6 months of treatment. Monitoring of liver function during treatment is recommended, particularly in the first few months. In men of advanced age with prostate cancer, bicalutamide monotherapy has been associated with an increase in non-prostate cancer mortality, in part due to an increase in the rate of heart failure. These mortality-related effects are thought to be a consequence of androgen deprivation, rather than due to a specific drug-related toxicity of bicalutamide.


title: Bicalutamide

text: There are 10 published case reports of liver toxicity associated with bicalutamide as of 2021. Death occurred in 2 of these cases. In all reported cases, the onset of toxicity was within the first 6 months of treatment. Symptoms that may indicate liver dysfunction include nausea, vomiting, abdominal pain, fatigue, anorexia, "flu-like" symptoms, dark urine, and jaundice. There are also published case reports of interstitial pneumonitis and eosinophilic lung disease associated with bicalutamide. Interstitial pneumonitis can potentially progress to pulmonary fibrosis and may be fatal. Symptoms that may indicate lung dysfunction include dyspnea (difficult breathing or shortness of breath), cough, and pharyngitis (inflammation of the pharynx, resulting in sore throat). Both hepatotoxicity and interstitial pneumonitis are said to be very rare events with bicalutamide. A few cases of photosensitivity have been reported with bicalutamide. Hypersensitivity reactions (drug allergy) like angioedema and hives have also uncommonly been reported in association with bicalutamide.


title: Bicalutamide

text: Because it is an antiandrogen, bicalutamide has a theoretical risk of birth defects like ambiguous genitalia and brain feminization in male fetuses. Due to its teratogenic capacity, contraception should be used in women taking bicalutamide who are fertile and sexually active.


title: Bicalutamide

text: The side effect profile of bicalutamide in men and women differs from that of other antiandrogens and is considered favorable in comparison. Relative to analogues and the steroidal antiandrogen (SAA) cyproterone acetate (CPA), bicalutamide monotherapy has a much lower incidence and severity of hot flashes and sexual dysfunction. In addition, unlike analogues and , bicalutamide monotherapy is not associated with decreased bone mineral density or osteoporosis. Conversely, bicalutamide monotherapy is associated with much higher rates of breast tenderness, gynecomastia, and feminization in men than analogues and . However, gynecomastia with bicalutamide is rarely severe and discontinuation rates due to this side effect are fairly low. These differences in side effects between bicalutamide monotherapy, analogues, and are attributed to the fact that whereas analogues and suppress estrogen production, bicalutamide monotherapy does not lower estrogen levels and in fact actually increases them.


title: Bicalutamide

text: Bicalutamide does not share the risk of neuropsychiatric side effects like depression and fatigue as well as cardiovascular side effects like coagulation changes, blood clots, fluid retention, ischemic cardiomyopathy, and adverse serum lipid changes that has been associated with. It has a much lower risk of hepatotoxicity than flutamide and and of interstitial pneumonitis than nilutamide. The drug also does not share the unique risks of diarrhea with flutamide and nausea, vomiting, visual disturbances, and alcohol intolerance with nilutamide. Unlike enzalutamide, bicalutamide is not associated with seizures or related central side effects like anxiety and insomnia. However, although the risk of adverse liver changes with bicalutamide is low, enzalutamide differs from bicalutamide in having no known risk of elevated liver enzymes or hepatotoxicity. In contrast to the spironolactone, bicalutamide does not have antimineralocorticoid effects, and hence is not associated with hyperkalemia, urinary frequency, dehydration, hypotension, or other related side effects. In women, unlike and spironolactone, bicalutamide does not produce menstrual irregularity or amenorrhea and does not interfere with ovulation or fertility.


title: Bicalutamide

text: A single oral dose of bicalutamide in humans that results in symptoms of overdose or that is considered to be life-threatening has not been established. Dosages of up to 600 mg/day have been well tolerated in clinical trials, and it is notable that there is a saturation of absorption with bicalutamide such that circulating levels of its active ("R")-enantiomer do not further increase above a dosage of 300 mg/day. Overdose is considered unlikely to be life-threatening with bicalutamide or other first-generation (i.e., flutamide and nilutamide). A massive overdose of nilutamide (13 grams, or 43 times the normal maximum 300 mg/day clinical dosage) in a 79-year-old man was uneventful, producing no clinical signs, symptoms, or toxicity. There is no specific antidote for bicalutamide or overdose, and treatment should be based on symptoms, if any are present.


title: Bicalutamide

text: Bicalutamide is almost exclusively metabolized by CYP3A4. As such, its levels in the body may be altered by inhibitors and inducers of CYP3A4. (For a list of CYP3A4 inhibitors and inducers, see here.) However, in spite of the fact bicalutamide is metabolized by CYP3A4, there is no evidence of clinically significant drug interactions when bicalutamide at a dosage of 150 mg/day or less is co-administered with drugs that inhibit or induce cytochrome P450 enzyme activity.


title: Bicalutamide

text: "In-vitro" studies suggest that bicalutamide may be able to inhibit CYP3A4 and, to a lesser extent, CYP2C9, CYP2C19, and CYP2D6. Conversely, animal studies suggest that bicalutamide may induce cytochrome P450 enzymes. In a clinical study, bicalutamide co-administered with the CYP3A4 substrate midazolam caused only a small and statistically non-significant increase in midazolam levels (+27%) presumably due to CYP3A4 inhibition. However, this was well below increases in midazolam exposure with potent CYP3A4 inhibitors like ketoconazole (+1500%), itraconazole (+1000%), and erythromycin (+350%), and is considered to not be clinically important. There is no indication of clinically significant enzyme inhibition or induction with bicalutamide at doses of 150mg/day or below.


title: Bicalutamide

text: Because bicalutamide circulates at relatively high concentrations and is highly protein-bound, it has the potential to displace other highly protein-bound drugs like warfarin, phenytoin, theophylline, and aspirin from plasma binding proteins. This could, in turn, result in increased free concentrations of such drugs and increased effects and/or side effects, potentially necessitating dosage adjustments. Bicalutamide has specifically been found to displace coumarin anticoagulants like warfarin from their plasma binding proteins (namely albumin) "in vitro", potentially resulting in an increased anticoagulant effect, and for this reason, close monitoring of prothrombin time and dosage adjustment as necessary is recommended when bicalutamide is used in combination with these drugs. However, in spite of this, no conclusive evidence of an interaction between bicalutamide and other drugs was found in clinical trials of nearly 3,000 patients.


title: Bicalutamide

text: Bicalutamide acts as a highly selective competitive silent antagonist of the ( = 159–243 nM), the major biological target of the androgen sex hormones testosterone and , and hence is an antiandrogen. The activity of bicalutamide lies in the ("R")-isomer. Due to its selectivity for the , bicalutamide does not interact importantly with other steroid hormone receptors and hence has no clinically relevant off-target hormonal activity (e.g., progestogenic, estrogenic, glucocorticoid, antimineralocorticoid). However, it has been reported that bicalutamide has weak affinity for the progesterone receptor (PR), where it is an antagonist, and hence it could have some antiprogestogenic activity. Bicalutamide does not inhibit 5α-reductase nor is known to inhibit other enzymes involved in androgen steroidogenesis (e.g., CYP17A1). Although it does not bind to the estrogen receptors (ERs), bicalutamide can increase estrogen levels secondarily to blockade when used as a monotherapy in males, and hence can have some "indirect" estrogenic effects in males. Bicalutamide neither suppresses nor inhibits androgen production in the body (i.e., it does not act as an antigonadotropin or androgen steroidogenesis inhibitor or lower androgen levels) and hence exclusively mediates its antiandrogenic effects by antagonizing the . In addition to the classical nuclear , bicalutamide has been assessed at the membrane androgen receptors (mARs) and found to act as a potent antagonist of ZIP9 ( = 66.3 nM), whereas it does not appear to interact with GPRC6A.


title: Bicalutamide

text: The affinity of bicalutamide for the is relatively low as it is approximately 30 to 100 times lower than that of , which is 2.5- to 10-fold as potent as an agonist as testosterone in bioassays and is the main endogenous ligand of the receptor in the prostate gland. However, typical clinical dosages of bicalutamide result in circulating levels of the drug that are thousands of times higher than those of testosterone and , allowing it to powerfully prevent them from binding to and activating the receptor. This is especially true in the case of surgical or medical castration, in which testosterone levels in the circulation are approximately 95% reduced and levels in the prostate gland are about 50 to 60% reduced. In women, levels of testosterone are substantially lower (20- to 40-fold) than in men, so much smaller doses of bicalutamide (e.g., 25 mg/day in the hirsutism studies) are necessary.


title: Bicalutamide

text: Blockade of the by bicalutamide in the pituitary gland and hypothalamus results in prevention of the negative feedback of androgens on the hypothalamic–pituitary–gonadal axis (HPG axis) in males and consequent disinhibition of pituitary luteinizing hormone (LH) secretion. This, in turn, results in an increase in circulating levels and activation of the gonadal production of testosterone and by extension production of estradiol. Levels of testosterone have been found to increase 1.5- to 2-fold (59–97% increase) and levels of estradiol about 1.5- to 2.5-fold (65–146% increase) in men treated with 150 mg/day bicalutamide monotherapy. In addition to testosterone and estradiol, there are smaller increases in concentrations of , sex hormone-binding globulin, and prolactin. Estradiol levels with bicalutamide monotherapy are similar to those in the low-normal premenopausal female range while testosterone levels generally remain in the high end of the normal male range. Testosterone concentrations do not typically exceed the normal male range due to negative feedback on the axis by the increased concentrations of estradiol. Bicalutamide influences the axis and increases hormone levels only in men and not also in women. This is due to the much lower levels of androgens in women and their lack of basal suppression of the axis in this sex. As evidenced by its effectiveness in the treatment of prostate cancer and other androgen-dependent conditions, the antiandrogenic actions of bicalutamide considerably exceed any impact of the increased levels of testosterone it results in. However, the elevated levels of estradiol remain unopposed by bicalutamide and are responsible for the gynecomastia and feminizing side effects it causes in men. Although bicalutamide monotherapy increases gonadotropin and sex hormone levels in men, this will not occur if bicalutamide is combined with an antigonadotropin such as a analogue, estrogen, or progestogen, as these medications maintain negative feedback on the HPG axis.


title: Bicalutamide

text: Under normal circumstances, bicalutamide has no capacity to activate the . However, in prostate cancer, mutations and overexpression of the can accumulate in prostate gland cells which can convert bicalutamide from an antagonist of the into an agonist. This can result in paradoxical stimulation of prostate cancer growth with bicalutamide and is responsible for the phenomenon of the antiandrogen withdrawal syndrome, where antiandrogen discontinuation paradoxically slows the rate of prostate cancer growth.


title: Bicalutamide

text: In transgender women, breast development is a desired effect of antiandrogen or estrogen treatment. Breast development and gynecomastia induced by bicalutamide is thought to be mediated by increased activation of the secondary to blockade of the (resulting in disinhibition of the in breast tissue) and increased levels of estradiol. In addition to fat deposition, connective tissue growth, and ductal development, bicalutamide has been found to produce moderate lobuloalveolar development of the breasts. However, full lobuloalveolar maturation necessary for lactation and breastfeeding will not occur without progestogen treatment.


title: Bicalutamide

text: Bicalutamide monotherapy seems to have minimal effect on testicular spermatogenesis, testicular ultrastructure, and certain aspects of male fertility. This seems to be because testosterone levels in the testes (where ≈95% of testosterone in males is produced) are extremely high (up to 200-fold higher than circulating levels) and only a small fraction (less than 10%) of the normal levels of testosterone in the testes are actually necessary to maintain spermatogenesis. As a result, bicalutamide appears to not be able to compete with testosterone in this sole part of the body to an extent sufficient to considerably interfere with androgen signaling and function. However, while bicalutamide does not seem to be able to adversely influence testicular spermatogenesis, it may interfere with -dependent sperm maturation and transport outside of the testes in the epididymides and vas deferens where androgen levels are far lower, and hence may still be able to impair male fertility. In addition, the combination of bicalutamide with other medications, such as estrogens, progestogens, and analogues, can compromise spermatogenesis due to their own adverse effects on male fertility. These medications are able to strongly suppress gonadal androgen production, which can severely impair or abolish testicular spermatogenesis, and estrogens also appear to have direct and potentially long-lasting cytotoxic effects in the testes at sufficiently high concentrations.


title: Bicalutamide

text: Bicalutamide has been found to act as an inhibitor or inducer of certain cytochrome P450 enzymes including CYP3A4, CYP2C9, CYP2C19, and CYP2D6 in preclinical research, but no evidence of this has been found in humans treated with up to 150 mg/day. It has also been identified "in vitro" as a strong inhibitor of CYP27A1 (cholesterol 27-hydroxylase) and as an inhibitor of CYP46A1 (cholesterol 24-hydroxylase), but this has yet to be assessed or confirmed "in vivo" or in humans and the clinical significance remains unknown. Bicalutamide has been found to be a P-glycoprotein (ABCB1) inhibitor. Like other first-generation and enzalutamide, it has been found to act as a weak non-competitive inhibitor of GABA receptor-mediated currents "in vitro" ( = 5.2 μM). However, unlike enzalutamide, bicalutamide has not been found to be associated with seizures or other related adverse central effects, so the clinical relevance of this finding is uncertain.


title: Bicalutamide

text: Though its absolute bioavailability in humans is unknown, bicalutamide is known to be extensively and well-absorbed. Its absorption is not affected by food. The absorption of bicalutamide is linear at doses up to 150 mg/day and is saturable at doses above this, with no further increases in steady-state levels of bicalutamide occurring at doses above 300 mg/day. Whereas absorption of ("R")-bicalutamide is slow, with levels peaking at 31 to 39 hours after a dose, ("S")-bicalutamide is much more rapidly absorbed. Steady-state concentrations of the drug are reached after 4 to 12 weeks of treatment independently of dosage, with a 10- to 20-fold progressive accumulation in levels of ("R")-bicalutamide. The long time to steady-state levels is the result of bicalutamide's very long elimination half-life.


title: Bicalutamide

text: The tissue distribution of bicalutamide is not well-characterized. The amount of bicalutamide in semen that could potentially be transferred to a female partner during sexual intercourse is low and is not thought to be important. Based on animal studies with rats and dogs it was thought that bicalutamide could not cross the blood–brain barrier and hence could not enter the brain. As such, it was initially thought to be a peripherally selective antiandrogen. However, subsequent clinical studies found that this was not also the case for humans, indicating species differences; bicalutamide crosses into the human brain and, in accordance, produces effects and side effects consistent with central antiandrogenic action. Bicalutamide is highly plasma protein bound (96.1% for racemic bicalutamide, 99.6% for ("R")-bicalutamide) and is bound mainly to albumin, with negligible binding to and corticosteroid-binding globulin.


title: Bicalutamide

text: Bicalutamide is metabolized in the liver. ("R")-Bicalutamide is metabolized slowly and almost exclusively via hydroxylation by CYP3A4 into ("R")-hydroxybicalutamide. This metabolite is then glucuronidated by UGT1A9. In contrast to ("R")-bicalutamide, ("S")-bicalutamide is metabolized rapidly and mainly by glucuronidation (without hydroxylation). None of the metabolites of bicalutamide are known to be active and levels of the metabolites are low in plasma, where unchanged biclautamide predominates. Due to the stereoselective metabolism of bicalutamide, ("R")-bicalutamide has a far longer terminal half-life than ("S")-bicalutamide and its levels are about 10- to 20-fold higher in comparison following a single dose and 100-fold higher at steady-state. ("R")-Bicalutamide has a relatively long elimination half-life of 5.8 days with a single dose and 7 to 10 days following repeated administration.


title: Bicalutamide

text: Bicalutamide is eliminated in similar proportions in feces (43%) and urine (34%), while its metabolites are eliminated roughly equally in urine and bile. The drug is excreted to a substantial extent in unmetabolized form, and both bicalutamide and its metabolites are eliminated mainly as glucuronide conjugates. The glucuronide conjugates of bicalutamide and its metabolites are eliminated from the circulation rapidly, unlike unconjugated bicalutamide.


title: Bicalutamide

text: The pharmacokinetics of bicalutamide are not affected by consumption of food, a person's age or body weight, renal impairment, or mild-to-moderate hepatic impairment. However, steady-state levels of bicalutamide are higher in Japanese individuals than in white people.


title: Bicalutamide

text: Bicalutamide is a racemic mixture consisting of equal proportions of enantiomers ("R")-bicalutamide (dextrorotatory) and ("S")-bicalutamide (levorotatory). Its systematic name () is ("RS")-"N"-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide. The compound has a chemical formula of CHFNOS, a molecular weight of 430.373 g/mol, and is a fine white to off-white powder.


title: Bicalutamide

text: The acid dissociation constant (pKa') of bicalutamide is approximately 12. It is a highly lipophilic compound (log P = 2.92). At 37 °C (98.6 °F), or normal human body temperature, bicalutamide is practically insoluble in water (4.6 mg/L), acid (4.6 mg/L at pH 1), and alkali (3.7 mg/L at pH 8). In organic solvents, it is slightly soluble in chloroform and absolute ethanol, sparingly soluble in methanol, and freely soluble in acetone and tetrahydrofuran.


title: Bicalutamide

text: Bicalutamide is a synthetic and nonsteroidal compound which was derived from flutamide. It is a bicyclic compound (has two rings) and can be classified as and has variously been referred to as an anilide ("N"-phenylamide) or aniline, a diarylpropionamide, and a toluidide.


title: Bicalutamide

text: First-generation including bicalutamide, flutamide, and nilutamide are all synthetic, nonsteroidal anilide derivatives and structural analogues of each other. Bicalutamide is a diarylpropionamide while flutamide is a monoarylpropionamide and nilutamide is a hydantoin. Bicalutamide and flutamide, though not nilutamide, can also be classified as toluidides. All three of the compounds share a common 3-trifluoromethylaniline moiety. Bicalutamide is a modification of flutamide in which a 4-fluorophenylsulfonyl moiety has been added and the nitro group on the original phenyl ring has been replaced with a cyano group. Topilutamide, also known as fluridil, is another that is closely related structurally to the first-generation , but, in contrast to them, is not used in the treatment of prostate cancer and is instead used exclusively as a topical antiandrogen in the treatment of pattern hair loss.


title: Bicalutamide

text: The second-generation enzalutamide and apalutamide were derived from and are analogues of the first-generation , while another second-generation , darolutamide, is said to be structurally distinct and chemically unrelated to the other . Enzalutamide is a modification of bicalutamide in which the inter-ring linking chain has been altered and cyclized into a 5,5-dimethyl-4-oxo-2-thioxo imidazolidine moiety. In apalutamide, the 5,5-dimethyl groups of the imidazolidine ring of enzalutamide are cyclized to form an accessory cyclobutane ring and one of its phenyl rings is replaced with a pyridine ring.


title: Bicalutamide

text: The first nonsteroidal androgens, the arylpropionamides, were discovered via structural modification of bicalutamide. Unlike bicalutamide (which is purely antiandrogenic), these compounds show tissue-selective androgenic effects and were classified as selective androgen receptor modulators (SARMs). Lead of this series included acetothiolutamide, enobosarm (ostarine; S-22), and andarine (acetamidoxolutamide or androxolutamide; S-4). They are very close to bicalutamide structurally, with the key differences being that the linker sulfone of bicalutamide has been replaced with an ether or thioether group to confer agonism of the and the 4-fluoro atom of the pertinent phenyl ring has been substituted with an acetamido or cyano group to eliminate reactivity at the position.


title: Bicalutamide

text: A few radiolabeled derivatives of bicalutamide have been developed for potential use as radiotracers in medical imaging. They include [F]bicalutamide, 4-[Br]bromobicalutamide, and [Br]bromo-thiobicalutamide. The latter two were found to have substantially increased affinity for the relative to that of bicautamide. However, none of these agents have been evaluated in humans.


title: Bicalutamide

text: 5"N"-Bicalutamide, or 5-azabicalutamide, is a minor structural modification of bicalutamide which acts as a reversible covalent antagonist of the and has approximately 150-fold higher affinity for the and about 20-fold greater functional inhibition of the relative to bicalutamide. It is among the most potent antagonists to have been developed and is being researched for potential use in the treatment of antiandrogen-resistant prostate cancer.


title: Bicalutamide

text: A number of chemical syntheses of bicalutamide have been published in the literature. The procedure of the first published synthesis of bicalutamide can be seen below.


title: Bicalutamide

text: Bicalutamide as well as all of the other currently marketed were derived from structural modification of flutamide, which itself was originally synthesized as a bacteriostatic agent in 1967 at Schering Plough Corporation and was subsequently and serendipitously found to possess antiandrogenic activity. Bicalutamide was discovered by Tucker and colleagues at Imperial Chemical Industries (ICI) in the 1980s and was selected for development from a group of over 2,000 synthesized compounds. It was first patented in 1982 and was first reported in the scientific literature in June 1987.


title: Bicalutamide

text: Bicalutamide was first studied in a phase I clinical trial in 1987 and the results of the first phase II clinical trial in prostate cancer were published in 1990. The pharmaceutical division of was split out into an independent company called Zeneca in 1993, and in April and May 1995, Zeneca (now AstraZeneca, after merging with Astra AB in 1999) began pre-approval marketing of bicalutamide for the treatment of prostate cancer in the . It was first launched in the in May 1995, and was subsequently approved by the on 4 October 1995, for the treatment of prostate cancer at a dosage of 50 mg/day in combination with a analogue.


title: Bicalutamide

text: Following its introduction for use in combination with a analogue, bicalutamide was developed as a monotherapy at a dosage of 150 mg/day for the treatment of prostate cancer, and was approved for this indication in Europe, Canada, and a number of other countries in the late 1990s and early 2000s. This application of bicalutamide was also under review by the in the in 2002, but ultimately was not approved in this country. In Japan, bicalutamide is licensed at a dosage of 80 mg/day alone or in combination with a analogue for prostate cancer. The unique 80 mg dosage of bicalutamide used in Japan was selected for development in this country on the basis of observed pharmacokinetic differences with bicalutamide in Japanese men.


title: Bicalutamide

text: Subsequent to negative findings of bicalutamide monotherapy for in the clinical programme, approval of bicalutamide for use specifically in the treatment of was withdrawn in a number of countries including the (in October or November 2003) and several other European countries and Canada (in August 2003). In addition, the and Canada explicitly recommended against the use of 150 mg/day bicalutamide for this indication. The drug is effective for, remains approved for, and continues to be used in the treatment of and , on the other hand.


title: Bicalutamide

text: The patent protection of bicalutamide expired in the in March 2009 and the drug has subsequently been available as a generic, at greatly reduced cost.


title: Bicalutamide

text: Bicalutamide was the fourth antiandrogen (and the third ) to be introduced for the treatment of prostate cancer, following the in 1973 and the flutamide in 1983 (1989 in the ) and nilutamide in 1989 (1996 in the ). It has been followed by abiraterone acetate in 2011, enzalutamide in 2012, apalutamide in 2018, and darolutamide in 2019, and may also be followed by in-development drugs such as proxalutamide and seviteronel.


title: Bicalutamide

text: "Bicalutamide" is the generic name of the drug in English and French and its , , , , , , and . It is also referred to as "bicalutamidum" in Latin, "bicalutamida" in Spanish and Portuguese, "bicalutamid" in German, and "bikalutamid" in Russian and other Slavic languages. The "bica-" prefix corresponds to the fact that bicalutamide is a "bicyclic" compound, while the "-lutamide" suffix is the standard suffix for . Bicalutamide is also known by its former developmental code name -176,334.


title: Bicalutamide

text: Bicalutamide is marketed by AstraZeneca in oral tablet form under the brand names Casodex, Cosudex, Calutide, Calumid, and Kalumid in many countries. It is also marketed under the brand names Bicadex, Bical, Bicalox, Bicamide, Bicatlon, Bicusan, Binabic, Bypro, Calutol, and Ormandyl among others in various countries. The drug is sold under a large number of generic trade names such as Apo-Bicalutamide, Bicalutamide Accord, Bicalutamide Actavis, Bicalutamide Bluefish, Bicalutamide Kabi, Bicalutamide Sandoz, and Bicalutamide Teva as well. A combination formulation of bicalutamide and goserelin is marketed by AstraZeneca in Australia and New Zealand under the brand name ZolaCos-CP.


title: Bicalutamide

text: Bicalutamide is off-patent and available as a generic. Unlike bicalutamide, the newer enzalutamide is still on-patent, and for this reason, is considerably more expensive in comparison.


title: Bicalutamide

text: The patent protection of all three of the first-generation has expired and flutamide and bicalutamide are both available as low-cost generics. Nilutamide, on the other hand, has always been a poor third competitor to flutamide and bicalutamide and, in relation to this fact, has not been developed as a generic and is only available as brand name Nilandron, at least in the


title: Bicalutamide

text: Bicalutamide is considerably less costly than analogues, which, in spite of some having been off-patent many years, have been reported (in 2013) to typically cost –$15,000 per year (or about per month) of treatment.


title: Bicalutamide

text: Sales of bicalutamide (as Casodex) worldwide peaked at US$1.3 billion in 2007, and it has been described as a "billion-dollar-a-year" drug prior to losing its patent protection starting in 2007. In 2014, despite the introduction of abiraterone acetate in 2011 and enzalutamide in 2012, bicalutamide was still the most commonly prescribed drug in the treatment of metastatic castration-resistant prostate cancer (mCRPC). Moreover, in spite of being off-patent, bicalutamide was said to still generate a few hundred million dollars in sales per year for AstraZeneca. Total worldwide sales of brand name Casodex were approximately US$13.4 billion as of the end of 2018.


title: Bicalutamide

text: Between January 2007 and December 2009 (a period of three years), 1,232,143 prescriptions of bicalutamide were dispensed in the , or about 400,000 prescriptions per year. During that time, bicalutamide accounted for about 87.2% of the market, while flutamide accounted for 10.5% of it and nilutamide for 2.3% of it. Approximately 96% of bicalutamide prescriptions were written for diagnosis codes that clearly indicated neoplasm. About 1,200, or 0.1% of bicalutamide prescriptions were dispensed to pediatric patients (age 0–16).


title: Bicalutamide

text: Bicalutamide is a prescription drug. It is not specifically a controlled substance in any country and therefore is not an illegal drug. However, the manufacture, sale, distribution, and possession of prescription drugs are all still subject to legal regulation throughout the world.


title: Bicalutamide

text: Bicalutamide has been studied in combination with the 5α-reductase inhibitors finasteride and dutasteride in prostate cancer. It has also been studied in combination with raloxifene, a selective estrogen receptor modulator (SERM), for the treatment of prostate cancer. Bicalutamide has been tested for the treatment of -positive /-negative locally advanced and metastatic breast cancer in women in a phase II study for this indication. Enzalutamide is also being investigated for this type of cancer. Bicalutamide has also been studied in a phase II clinical trial for ovarian cancer in women.


title: Bicalutamide

text: Bicalutamide has been studied in the treatment of benign prostatic hyperplasia (BPH) in a 24-week trial of 15 patients at a dosage of 50 mg/day. Prostate volume decreased by 26% in patients taking bicalutamide and urinary irritative symptom scores significantly decreased. Conversely, peak urine flow rates and urine pressure flow examinations were not significantly different between bicalutamide and placebo. The decrease in prostate volume achieved with bicalutamide was comparable to that observed with the 5α-reductase inhibitor finasteride, which is approved for the treatment of BPH. Breast tenderness (93%), gynecomastia (54%), and sexual dysfunction (60%) were all reported as side effects of bicalutamide at the dosage used in the study, although no treatment discontinuations due to adverse effects occurred and sexual functioning was maintained in 75% of patients.


title: Bicalutamide

text: A phase III clinical trial of bicalutamide in combination with an ethinylestradiol-containing combined oral contraceptive for the treatment of severe hirsutism in women with was completed in Italy in 2017 under supervision of the Italian Agency for Drugs (AIFA).


title: Bicalutamide

text: Antiandrogens have been suggested for treating COVID-19 in men and as of May 2020 high-dose bicalutamide is in a phase II clinical trial for this purpose.


title: Bicalutamide

text: Bicalutamide may be used to treat hyperandrogenism and associated benign prostatic hyperplasia secondary to hyperadrenocorticism (caused by excessive adrenal androgens) in male ferrets. However, it has not been formally assessed in controlled studies for this purpose.


title: Sonic the Hedgehog (OVA)

text: Unlike other "Sonic the Hedgehog" media, the setting of the series is in the world of Planet Freedom, which is split into two distinct realms: the Land of the Sky and the Land of Darkness.


title: Sonic the Hedgehog (OVA)

text: The Land of the Sky consists of an unknown number of continents that drift high in the stratosphere of the planet, all of them connected to a massive ice formation which also serves to anchor them to the planet's surface below. According to Knuckles, if this ice network was destroyed, Planet Freedom's rotation would hurl the Land of the Sky into outer space, undoubtedly killing everyone on it.


title: Sonic the Hedgehog (OVA)

text: The Land of Darkness is the actual surface of Planet Freedom, a post-apocalyptic wilderness with the dastardly Robotnik as its sole living inhabitant. The Land of Darkness can only be accessed in one of two ways: by a whirlwind-like "portal" in the Land of the Sky, or via a warp zone, an extradimensional link between two points on Planet Freedom. Most of its terrain is untamed and mountainous, but a crumbling city serves as the location of Robotnik's empire. The city and terrain strongly imply that Planet Freedom is a post apocalyptic Earth that was built upon with floating islands, with certain landmarks suggesting that the ruins are those of New York City.


title: Sonic the Hedgehog (OVA)

text: Sonic the Hedgehog is relaxing on the beach of South Island with Miles "Tails" Prower, when Old Man Owl arrives with a message from the President asking Sonic to come to his office. Once there, they discover Dr. Robotnik has taken the President and his daughter Sara prisoner. After giving exposition of how Planet Freedom works (explaining the two "dimensions" of the planet, The Land of the Sky, and The Land of Darkness), Robotnik explains that a giant mecha named Metal Robotnik ("Black Eggman" in the original Japanese release) has exiled him from his utopian city of Robotropolis ("Eggmanland" in the original) and sabotaged the Robot Generator, which will explode by sunrise the next day. He asks Sonic to head to the Land of Darkness to stop it in exchange for the President and Sara's lives. Once there, Metal Robotnik tries to stop them from reaching the generator. Knuckles the Echidna arrives and rescues them, and all three team up to destroy the mecha. Unbeknownst to them, Metal Robotnik is revealed to have been controlled by Robotnik, with Sara unwillingly in tow. The episode ends with Sonic, Tails, and Knuckles heading to Robotropolis.


title: Sonic the Hedgehog (OVA)

text: After entering Robotropolis, Knuckles distracts the enemy robots while Sonic and Tails try to stop the generator in the heart of the city. They arrive just in time, but when Sonic pulls the lever, the machine traps him and scans his body. Knuckles frees Sonic just as the machine crumbles to the ground, revealing Dr. Robotnik's newest robot, Hyper Metal Sonic. Dr. Robotnik appears in Metal Robotnik's remains and reveals he lured Sonic to copy his mind, personality, and abilities for Hyper Metal Sonic. Sonic and Metal battle, but Metal easily overpowers Sonic. Tails and Knuckles return to the Land of the Sky, where Tails learns that Metal is out to destroy the planet by digging into the ice caps that hold the Land of the Sky together, allowing lava to emerge and melt the ice. Sonic wakes up in Green Lake City and returns to the Presidential Palace, learning of Metal's goal from the President.


title: Sonic the Hedgehog (OVA)

text: Sonic, Tails, and Knuckles go to the ice caps, where Sara is being held hostage by Robotnik, planning to marry her so the two will rule over Planet Freedom after the Land of the Sky's decimation. Sonic encounters Metal and the two have a lengthy battle. Tails manage to corrupt Metal's data, and Sonic severely damages him. During the altercation, the President and Old Man arrive and are trapped in their aircraft, but Metal saves them. Sonic realizes that Metal does have emotions, as he was programmed with Sonic's persona and instincts. Metal gets blown into a crack and falls into a subglacial volcano. Sonic reaches out his hand to help him, but Metal rejects it, telling him "there is only one Sonic" before being destroyed by the rising magma. Robotnik states he still has Sonic's DNA and can re-build Metal Sonic, but one of his missiles from the fight inadvertently blows up the disc containing Sonic's DNA. Knuckles then punches Sonic as revenge for Sonic accidentally stepping on him during the brawl, and the two get into a chase, with all the others following behind, ending the episode.


title: Sonic the Hedgehog (OVA)

text: The OVA series was produced by Studio Pierrot, Sega Enterprises and General Entertainment under the supervision of Sonic Team, Yuji Naka and Naoto Ohshima. It is directed and storyboarded by Kazuho Ikegami, with Mayori Sekijima handling the story structure, Masashi Kubota writing the scripts, Tsuneo Ninomiya designing the characters and Mitsuhiro Tada composing the music. Both episodes feature an ending theme "LOOK-ALIKE," composed and arranged by Tada and written and sung by Riyu Konaka. The OVA was originally distributed by Taki Corporation in Japan on a rental-only basis between January 26 and March 22 before being released for retail sale on May 31, 1996.


title: Sonic the Hedgehog (OVA)

text: ADV Films announced they had licensed the OVA series at Project A-Kon 9, which took place in May 1998. It was dubbed in English and released as a single direct-to-video film titled Sonic the Hedgehog: The Movie on VHS and DVD on September 7, 1999, to coincide with the international release of "Sonic Adventure" for the Dreamcast. It was later re-released on DVD on January 13, 2004. Due to ADV Films being dissolved and its assets being spun off into Section23 Films and Sentai Filmworks, both releases are now out of print.


title: Sonic the Hedgehog (OVA)

text: In the United States, it reached number 7 on the "Billboard" video sales chart and number 6 on the "Billboard" kids' video sales chart.


title: Sonic the Hedgehog (OVA)

text: The March 1996 issue of the "DieHard Magazine" gave the OVA a positive review stating that "all in all, the artwork looks amazing, plus it's an O.V.A., so the artists have been given quite an extensive budget. The animation is much cleaner than you could ever expect from a TV show, but the characters on-screen presence is what really makes Sonic so cool. It's like playing the game, but in anime form. After the U.S. Sonic cartoon has been canceled, this anime is definitely a good choice."


title: Sonic the Hedgehog (OVA)

text: Henry Gilbert of GamesRadar approved of the concept of a colorful, fast-paced anime adaptation of "Sonic", noting the fights between Sonic and his evil counterpart, Metal Sonic, as "cool." This is unfortunately accompanied by "scenes of slapstick humor, anime cliches, and childish voice acting" as well as the "perpetually annoying" Sara.


title: Sonic the Hedgehog (OVA)

text: Chris Shepard of Anime News Network praised the OVA for its non-traditional action and said it was "good for Sonic fans". He called the English dub poor, and said the story "strayed from the video games a little too much" and it was "very basic".


title: Sonic the Hedgehog (OVA)

text: In 2020, 3GI Industries, who had previously created "Shrek Retold", released "Sonic Rebuilt", a recreation of the film by over 200 artists.


title: Suleyman Kerimov

text: Suleyman Abusaidovich Kerimov (; ; born 12 March 1966) is a Russia-based billionaire, oligarch, and politician of Lezgian origin. Kerimov has close ties to Vladimir Putin's government in Russia, as well as Ramzan Kadyrov, the Chechen leader.


title: Suleyman Kerimov

text: He entered politics in the 1990s. By 1999, he won control of Nafta Moskva, a former state-oil trader. In the 2000s, Kerimov obtained billions of dollars in loans from big Russian state-owned banks, such as Sberbank and VTB. Through these loans, he became a major stakeholder in Gazprom and Uralkali, as well as Sberbank. By 2008, his fortune had risen to $21 billion, and by 2022, it had decreased to $11 billion.


title: Suleyman Kerimov

text: Since 2008, Kerimov has represented the Republic of Dagestan in the Federation Council of Russia. In April 2018, he was placed under sanctions by the United States Department of Treasury. In the wake of 2022 Russian Invasion of Ukraine, Kerimov was sanctioned as a Russian oligarch close to President Putin, by the US, UK and EU on 15 March 2022. Kerimov's son Said Kerimov resigned from the board of Polyus Gold in April 2022 and the family sold its stake in the company worth $6.3 billion relinquishing the majority shareholder position of Polyus Gold.


title: Suleyman Kerimov

text: He bought Anzhi Makhachkala in 2011, which subsequently made numerous high-profile signings. The club bought Samuel Eto’o, making him the highest-paid player in the world. In 2013, Kerimov drastically and abruptly cut the team's funding, prompting a firesale of players.


title: Suleyman Kerimov

text: Kerimov was born in Derbent, Dagestan. He graduated from high school in 1983, and following this enrolled in the Civil Engineering Department at Dagestan Polytechnic Institute in 1984, though his obligatory military service for the Soviet Army brought his studies to a halt just one year later. After completing his service in 1986, Kerimov continued his studies at Dagestan State University, where he graduated with a degree in financial accounting and economics in 1989. During his studies he was Deputy Chairman of DSU's Trade Union Committee. It was also at university that Kerimov met his wife, Firuza, the daughter of a former Trade Union leader.


title: Suleyman Kerimov

text: Kerimov has stated to have dreamed of making money from an early age, an ambition that prompted him to later move from his native Dagestan in the early 1990s.


title: Suleyman Kerimov

text: Soon after his university graduation in 1989, Kerimov took a job as an economist at the Eltav electrical plant in Makhachkala, the capital of Dagestan. The state-controlled plant supplied transistors and semi-conductors to television-makers, while also producing diodes, microchips and halogen lamps. Kerimov was paid 150 roubles (approximately $250 dollars) a month and he and his wife lived in a worker's hostel attached to the plant, where they shared one room of a two-room flat.


title: Suleyman Kerimov

text: Eventually, Kerimov rose to the rank of Deputy Director General at Eltav and began to dabble in investing alongside during the fall of the Soviet Union.


title: Suleyman Kerimov

text: In 1993, Kerimov was put in charge of handling relations between Eltav and Fedprombank, a Moscow bank established by the electrical company. Fedprombank financed lagging industries and Kerimov and his associates soon became creditors to large utility companies, allowing them to continue to provide key services. Once the Russian economy stabilized, the debts were repaid with hefty returns for Fedprombank and, consequently, Kerimov.


title: Suleyman Kerimov

text: In 1995, Kerimov was appointed to head the banking and trading company Soyuz-Finans, and by 1997, Kerimov had built a 50% stake in Vnukovo Airlines and used his leverage to take over Fedprombank, buying out his partners’ shares.


title: Suleyman Kerimov

text: In late 1999, Kerimov bought a 55% stake in the oil trading company Nafta Moskva, the successor to the Soviet monopoly firm Soyuznefteexport, for $50 million. By 2000, he had increased his stake of Nafta Moskva to 100%. Kerimov undertook a mass restructuring of the company, selling off all of the oil-related aspects and creating an investment and holding company. Nafta's investments in the mid-2000s included purchase of the business center Smolensky Passazh and AvtoBank.


title: Suleyman Kerimov

text: In 2003, Kerimov managed to secure a $43 million loan from the state-owned Vnesheconombank, which he invested in the oil and gas company Gazprom. Within the next year, share prices for the Russian gas company doubled and Kerimov was able to pay off the entirety of the loan within four months. In 2004 Sberbank, now the largest bank in Russia and Eastern Europe, provided Kerimov with a loan of $3.2 billion., which was later repaid, and these funds were also invested in equities. By 2008, Kerimov had amassed a 5% stake in Gazprom, a 6% stake in Sberbank, along with an estimated fortune of $17.5 billion, making him the 36th richest man in the world. However, in mid-2008, Kerimov sold all his Gazprom and Sberbank shares.


title: Suleyman Kerimov

text: In November 2005, Kerimov's Nafta Moskva acquired JSC Polymetal, one of Russia's largest gold and silver mining companies. In 2007, he took the company public on the London Stock Exchange, then sold 70% of his shares in 2008 before gold would go on to climb to an all-time high in 2011. In 2008, Kerimov sold control over Polymetal.


title: Suleyman Kerimov

text: As markets around the world began to tighten in 2007, Kerimov and his associates expected that Russia would suffer more than the West from the impending economic crisis. A concerted effort was thus made to build closer ties with Western banks. Kerimov decreased his stakes in Gazprom and other Russian blue chips and approached Wall Street, proposing to invest the vast majority of his fortune to defend the institutions from short-sellers. In return, it was expected that Kerimov would receive favorable lending terms for future loans.


title: Suleyman Kerimov

text: In 2007, Kerimov invested billions in Morgan Stanley, Goldman Sachs, Deutsche Bank, Credit Suisse and other financial institutions. Though neither Kerimov nor the Western banks have disclosed the exact size of his investment, it was sizeable enough for Kerimov to receive a call from the United States Treasury during the darkest days of the economic crisis imploring the Russian oligarch not to sell his stakes.


title: Suleyman Kerimov

text: Following his losses during the economic crisis, Kerimov shifted his investment strategy to buying stakes large enough to influence the strategies of the companies he invests in. In 2009, Nafta Moskva bought a $1.3 billion stake (37% stake) in OAO Polyus Gold, Russia’s largest gold producer, from Vladimir Potanin.


title: Suleyman Kerimov

text: Later the stake was increased up to 40.2%. In 2012 the company held an IPO on the London Stock Exchange.


title: Suleyman Kerimov

text: In the spring of 2009, shareholders of Russia's construction giant PIK Group sold 25% of their company's shares to Kerimov. PIK required extra funding after their debt level reached $1.98 billion, and the value of their capital fell by more than 40 times to $279.9 million. Nafta Moskva later increased its stake in PIK Group to 38.3%.


title: Suleyman Kerimov

text: In December 2013 Kerimov sold his shares to property investor Sergei Gordeev and businessman Alexander Mamut, who owns a stake in precious metals miner Polymetal.


title: Suleyman Kerimov

text: In June 2010, Kerimov and his partners Alexander Nesis and Filaret Galchev together paid Dmitry Rybolovlev an estimated $5.3 billion for a 53% stake in Russian potash giant Uralkali, which, together with Belaruskali, at the time made up the duopoly that controlled 70% of the global potash market: the Belarusian Potash Company (BPC). Kerimov secured substantial loans from Russia's VTB bank for the Uralkali takeover.


title: Suleyman Kerimov

text: In July 2013, Uralkali announced it was pulling out of the BPC cartel, dropping prices and increasing production to maximum capacity in a grab for market share. The immediate consequences on the global economy were a 25% drop in potash prices to around $340 a tonne, harming the prospects of both Canadian producers and the Belarusian economy. Belarusian authorities estimate they may lose up to $1 billion a year.


title: Suleyman Kerimov

text: Two weeks after Uralkali's July announcement, Belarusian prime minister Mikhail Myasnikovich responded by inviting Kerimov and the Uralkali managers to Minsk to discuss the current situation. Uralkali's then-CEO attended in Kerimov's place and was arrested by state security forces and charged with "abuse of power".


title: Suleyman Kerimov

text: In the meantime, Belarus also opened a criminal investigation into other Uralkali employees and its main shareholder Suleyman Kerimov. Baumgertner was held in a Belarusian KGB jail until a plan to change ownership of Uralkali was announced, and Belarus then extradited Baumgertner to Russia. Belarus put Kerimov on the national wanted list, and also requested Interpol to publish a Red Notice for him. Interpol clarified later that no Red Notice had been issued and that the request was political in nature. The Belarusian authorities later withdrew the case against Kerimov and closed the criminal investigation. By December 2013, Kerimov sold 21.75% of Uralkali shares to Mikhail Prokhorov for US$3.7 billion and 19,99% (for approximately US$2.9 billion) to Uralchem.


title: Suleyman Kerimov

text: "Forbes" magazine describes Kerimov as one of the most private Russian billionaires, who has not given a single interview over 20 years in business.


title: Suleyman Kerimov

text: Moscow Times quoted a former deputy editor of "Forbes" Russia Kirill Vishnepolsky as describing Kerimov as a "Russian Warren Buffett" for a similarly astute investment style. A senior Moscow banker is reported to have said of Kerimov: "Sometimes it is difficult to talk to him. He is always a few steps ahead of you. For foreigners, it is next to impossible, even those used to a Russian environment. He is very quick and creative, in a sense that ideas come to him that don't come to other people". Kerimov reportedly made extensive use of leverage for his investments, according to financiers and bankers active in Russia.


title: Suleyman Kerimov

text: In 2011, Kerimov purchased FC Anzhi Makhachkala, his hometown football club which competes in the Russian Premier League.


title: Suleyman Kerimov

text: In March 2012, it was reported that Kerimov had given the club a summer transfer budget of over €230 million, in an attempt to qualify for the UEFA Champions League within the next three seasons.


title: Suleyman Kerimov

text: Apart from FC Anzhi, Kerimov financed the construction of a modern football stadium Anzhi Arena for 30,000 spectators and teams from Anzhi's Youth Football Academy.


title: Suleyman Kerimov

text: In August 2013, as a part of new long-term strategy for the club, it was decided to scale back the club's annual budget by $50–70 million, down from their previous outlay of $180 million a season. The club sold some international players and recruited Russian young players instead.


title: Suleyman Kerimov

text: Shortly after Kerimov bought into Nafta Moskva, the company found itself in a conflict with businessman Andrei Andreev. Andreev's assets were transferred to Nafta Moskva, Millhouse Capital and Basic Element. Further dispute brought the parties to the court.


title: Suleyman Kerimov

text: Nafta Moskva, controlled by Kerimov, acquired a 25% stake in the Hotel Moskva project, a multibillion-dollar project to construct a replica of the enormous Stalin-era luxury hotel demolished in 2004. in February 2009, closing the deal by January 2010. In September 2010, Member of Russian Parliament Ashot Egiazaryan accused Kerimov of conspiring with the city government of Moscow to forcibly acquire his 25% stake in the project. After claiming he received death threats, Egiazaryan fled to the United States to seek asylum and filed lawsuits in a civil court in Cyprus, the London Court of International Arbitration and on Capitol Hill claiming that a campaign of threats of criminal prosecution and armed police raids forced him to give up his shares. According to Kerimov's lawyer Mr Egiazaryan transferred his interest in the Moskva Hotel as part of a legitimate business deal but was overextended and was deep in debt. Mr Egiazaryan was facing financial ruin.


title: Suleyman Kerimov

text: Pending deliberation by the courts, Kerimov's assets were frozen, upsetting Uralkali’s $39 billion joint bid with Chinese company Sinochem for the Canadian Potash Corp. The Nicosia district court in Cyprus lifted Kerimov's billion dollar asset freeze in February 2011, arguing that the plaintiffs "failed to prove the urgency of their petition." According to Egiazaryan's lawyer, Andreas Haviaras, the Cyprus ruling was based on "technicalities" and did not prejudge the merits of the case.


title: Suleyman Kerimov

text: The hotel reopened in 2014 under the Four Seasons brand. In October 2015, Suleiman Kerimov sold his interest in the property to businessmen Yury and Alexey Khotin for an undisclosed amount.


title: Suleyman Kerimov

text: In November 2017, Kerimov was arrested by French police at Nice airport in connection with a tax evasion case concerning his alleged purchase of several luxury residences on the French Riviera via shell companies. The charges were dismissed the following June. In March 2019, French prosecutors placed Kerimov under formal investigation "on suspicion of complicity in tax fraud". He was released on bail of €20 million and his lawyer plans to appeal the accusation of fraud.


title: Suleyman Kerimov

text: Kerimov is one of many Russian "oligarchs" named in the Countering America's Adversaries Through Sanctions Act, CAATSA, signed into law by President Donald Trump in 2017.


title: Suleyman Kerimov

text: From 1999 to 2003, Kerimov was a member of the State Duma of the 3rd Convocation, the lower house of the Federal Assembly of Russia, as well as a member of the State Duma Committee for Security. From 2003 to 2007, while continuing his role on the Committee for Security, he was also a member of the 4th Convocation and Deputy Chairman of the State Duma Committee for Physical Education, Sports and Youth. He first gained a seat in parliament with the Liberal Democratic Party, led by Vladimir Zhirinovsky.


title: Suleyman Kerimov

text: Since 2008, Kerimov has served as a member of the Federation Council of the Federation Assembly of the Russian Federation – the upper house of the Federation Assembly— and represents the Republic of Dagestan. In response to the Russian parliament’s passage of a bill prohibiting government officials from holding foreign-issued securities and bank accounts abroad, Kerimov transferred his assets to the Suleyman Kerimov Foundation, a charity registered in Switzerland, in May 2013. This way, he retained both his position in the Federation Council and beneficiary rights to his business assets. Suleiman Kerimov was re-elected to the Federation Council in September 2016.


title: Suleyman Kerimov

text: Kerimov's father was a lawyer at a criminal investigation institution, while his mother was an accountant for the Savings Bank of Russia. He is married and has three children.


title: Suleyman Kerimov

text: In October 2011, Kerimov used his connections to fly Western financial figures such as Jamie Dimon of JPMorgan, Richard Parsons of Citigroup and Stephen Schwarzman of Blackstone to Moscow in support of Medvedev’s initiative to turn Moscow into an "international financial centre".


title: Suleyman Kerimov

text: In 2006 Kerimov was listed among the world's 100 richest people and as Russia's eighth richest man ranked by "Forbes". He had a net worth of $6.9 billion as of 2014, with the previous years' net worth estimated at $7.1 billion (2013) and $6.5 billion (2012).


title: Suleyman Kerimov

text: In 2020, Kerimov's fortune doubled due to a sharp rise in gold prices. In August 2020, he became the richest businessman in Russia for a while. His family's fortune almost entirely based on the 77 percent holding in Polyus gold company was estimated at $24.7 billion.


title: Suleyman Kerimov

text: At the end of 2020, the value of the assets of the Kerimov family was estimated at $20.9 billion. By 2022, his wealth had decreased to $11 billion. He keeps vast assets through networks of offshore companies.


title: Suleyman Kerimov

text: He owns a villa in Cap d’Antibes, France. On 26 November 2006, in Nice, France, Kerimov was seriously injured after losing control of a $650,000 Ferrari Enzo on the Promenade des Anglais. He suffered severe burns as a result of the accident.


title: Suleyman Kerimov

text: Known for spending much of his fortune on parties, the Russian billionaire has paid for celebrities such as Christina Aguilera, Shakira, Amy Winehouse and Jessie J to perform at his events.


title: Suleyman Kerimov

text: From 2005 to 2015, Kerimov owned one of the world's largest private yachts, which is known as "Ice". Previously known as "Air", she was built by German company Lürssen in 2005. "Ice" measures 295 feet (90 metres) in length, and can reach a speed of 18.6 knots (33 km/h; 21 mph). She has won the Superyacht of the Year award at the World Superyacht Awards in 2006, and is currently the 78th largest yacht in the world. He sold "Ice" to The Ministry of Defence for the Republic of Equatorial Guinea in 2015.


title: Suleyman Kerimov

text: In 2022 there were reports that he was the owner of the superyacht "Amadea". In April 2022, it was seized by Fiji police at Lautoka Port as Fijian high court granted a restraining order to Fiji Police to restrain it for being allegedly linked with Kerimov. In May 2022, Fiji's High Court ruled that US authorities can seize the yacht. A possible Fabergé egg was found aboard the yacht.


title: Suleyman Kerimov

text: Kerimov established the Suleyman Kerimov Foundation in 2007. The Kerimov Foundation has donated to mosque and church constructions, as well as sent thousands of pilgrims to Mecca on Hajj annually. Kerimov spent $100 million on the construction of the Moscow Cathedral Mosque.


title: Suleyman Kerimov

text: Kerimov was involved in the reconstruction of the Zarechenskaya secondary school, an advanced comprehensive school west of Moscow. Kerimov is a sponsor of the Sirius educational centre for gifted children, located in Sochi and Dagestan.


title: Suleyman Kerimov

text: Kerimov is head of the supervisory board of the Russian Wrestling Federation, and is a member of the Gorchakov Foundation's supervisory board. The International Federation of Associated Wrestling Styles (FILA) honored Kerimov the "Gold Medal" in 2013.


title: Suleyman Kerimov

text: On 20 March 2017, Kerimov was awarded the Order "For Merit to the Fatherland", II class by President Vladimir Putin for his outstanding contribution to the development of parliamentarianism and legislation.


title: Harmon Killebrew

text: Harmon Clayton Killebrew Jr. (; June 29, 1936May 17, 2011), nicknamed "The Killer" and "Hammerin' Harmon", was an American professional baseball first baseman, third baseman, and left fielder. He was a prolific power hitter who spent most of his 22-year career in Major League Baseball with the Minnesota Twins. At the time of his retirement Killebrew had the fifth-most home runs in major league history. He was second only to Babe Ruth in American League (AL) home runs, and was the AL career leader in home runs by a right-handed batter. Killebrew was inducted into the National Baseball Hall of Fame in 1984.


title: Harmon Killebrew

text: Killebrew was tall and 213 pounds (97 kg). His compact swing generated tremendous power and made him one of the most feared power hitters of the 1960s, when he hit at least 40 home runs in a season eight times. In total Killebrew led the league six times in home runs and three times in RBIs, and was named to 13 All-Star teams. In 1965, he played in the World Series with the Twins, who lost to the Los Angeles Dodgers. His finest season was 1969, when he hit 49 home runs, recorded 140 RBIs and won the AL Most Valuable Player Award while helping lead the Twins to the AL West pennant.


title: Harmon Killebrew

text: With quick hands and exceptional upper body strength, Killebrew was known for both the frequency and distance of his homers. He hit the longest home runs ever recorded at Minnesota's Metropolitan Stadium [], and Baltimore's Memorial Stadium [], and was the first of four players to hit a ball over the left field roof at Detroit's Tiger Stadium. Despite his nicknames and his powerful style of play, Killebrew was a quiet, kind man. Asked once what hobbies he had, Killebrew replied, "Just washing the dishes, I guess."


title: Harmon Killebrew

text: After retiring from baseball, Killebrew became a television broadcaster for several baseball teams from 1976 to 1988. He also served as a hitting instructor for the Oakland Athletics.


title: Harmon Killebrew

text: Born and raised in Payette, Idaho, Killebrew was youngest of four children of Harmon Clayton Sr. and Katherine Pearl (May) Killebrew. His father, a painter and sheriff, was a member of an undefeated Millikin College football team who was later named an All-American under eventual Pro Football Hall of Fame coach Greasy Neale. According to family legend, Harmon Killebrew's grandfather was the strongest man in the Union Army, winning every available heavyweight wrestling championship. Clayton encouraged Harmon and his brothers to stay active in various sports before his sudden death in 1953 at age 59.


title: Harmon Killebrew

text: As a child, Killebrew played baseball at Walter Johnson Memorial Field, named after the Hall of Fame pitcher who spent part of his childhood in Idaho. He worked as a farmhand in his youth, lifting ten-gallon milk cans, each weighing about . Killebrew earned 12 letters in various sports and was named an All-American quarterback at Payette High School; the school retired his uniform number. He was offered an athletic scholarship by the University of Oregon, but declined the offer.


title: Harmon Killebrew

text: In the early 1950s, Senator Herman Welker of Idaho told Washington Senators owner Clark Griffith about Killebrew, who was hitting for an .847 batting average for a semi-professional baseball team at the time. Griffith told his farm director Ossie Bluege about the tip and Bluege flew to Idaho to watch Killebrew play. The Boston Red Sox also expressed interest but Bluege succeeded in signing him to a $50,000 ($ today) contract on June 19, 1954.


title: Harmon Killebrew

text: Killebrew signed his contract under Major League Baseball (MLB)'s Bonus Rule, which required that he spend two full seasons on the major league roster. He made his major league debut four days after signing and six days from his 18th birthday (becoming the youngest active player in the majors at the time), running for pinch-hitter Clyde Vollmer, who had been hit by a pitch with the bases loaded by Chicago White Sox starter Jack Harshman. On August 23, 1954, Killebrew made his first start in the second game of a doubleheader against the Philadelphia Athletics, hitting two singles and a double as the Senators won, 10–3. A year and one day after making his major league debut, Killebrew hit his first major league home run on June 24, 1955, in the fifth inning off Detroit Tigers starter Billy Hoeft, five days shy of his 19th birthday. In his first two seasons, Killebrew struck out 34 times in only 93 at bats, contributing to a .215 batting average with four home runs. Killebrew also had defensive difficulties at third base, where he played behind veteran Eddie Yost.


title: Harmon Killebrew

text: When Killebrew's bonus period expired in 1956, he was sent to the Senators' minor league affiliate in Charlotte of the South Atlantic League. He returned to the majors in early May. On May 29, after being forced into action when regular second baseman Pete Runnels was injured early in a game against the Orioles, Killebrew hit two home runs, including only the second ball ever hit over a wire barrier in Baltimore's Memorial Stadium's center field. Killebrew had a .115 average through June 16, and as a result was sent back to Charlotte; he finished the season there with a .325 batting average and 15 home runs in 70 games. Killebrew spent most of the 1957 season with the Southern Association's Chattanooga Lookouts, where he hit a league-high 29 home runs with 101 RBIs and was named to the All-Star Game. While in Chattanooga, Killebrew became the only player to hit a home run over the center field wall at Engel Stadium, from home plate. In 1958, he was briefly promoted to Indianapolis of the American Association but struggled and was sent back to Chattanooga for most of the season. Killebrew finished the season with 38 games played in Indianapolis and 86 in Chattanooga, where he hit .308 with 17 home runs. He also played a combined 22 games for the Senators in 1957 and 1958.


title: Harmon Killebrew

text: Calvin Griffith took over the Senators after his uncle Clark Griffith died in 1955, and decided Killebrew was ready to become the Senators' regular third baseman. Griffith traded the 32-year-old Eddie Yost to the Detroit Tigers on December 6, 1958, and Killebrew became the starting third baseman. From May 1 to May 17, he had five multi-home run games and his first five-RBI game on May 12. With 28 home runs by mid-season, he started the first 1959 All-Star Game and was a reserve in the second. Killebrew attracted so much attention in Washington that he was visited by President Dwight D. Eisenhower, who frequently attended games, and Griffith turned down a $500,000 offer for Killebrew from the Cincinnati Reds. Killebrew finished the season with 42 home runs to tie for the American League lead; it also tied the Senators' single-season record set by his teammate Roy Sievers two years earlier. Although 1959 proved his breakout season, he was ineligible for the Rookie of the Year Award because of his previous sparse experience. Instead, the award went to teammate Bob Allison.


title: Harmon Killebrew

text: Killebrew was bothered by injury early in the 1960 season. In March, he had surgery for nasal irritation, and a recurring hamstring injury caused him to miss most of May. On his return, he remained in the lineup for the rest of the season, finishing the year with 31 home runs in 124 games. Killebrew's arrival and home runs did little to improve the Senators' record, as they finished in the second division of the American League every year he played for Washington, including four years in last place. After the 1960 season, the Senators moved to Minnesota and became the Minnesota Twins.


title: Harmon Killebrew

text: For the franchise's first year in Minnesota, Killebrew was named team captain by manager Cookie Lavagetto. He responded by hitting 46 home runs, breaking the franchise record he had tied two years earlier. Among his other production, Killebrew drove in a team-leading 122 RBIs, posted a career-best batting average of .288 and had a slugging percentage of over .600 for the only time in his career. In addition, he had a career-high seven triples, tying for the team lead, and led the Twins in runs, total bases and walks. On June 12, 1961, Killebrew had the only five-hit game of his career, though in a losing effort. Killebrew was named to both 1961 All-Star games. He did not play in the second, but in the first, he hit a pinch hit home run in the sixth inning. After the season ended, Killebrew took part in a home run hitting contest with Jim Gentile and Roger Maris, whose 61 home runs that year broke the single-season record; Killebrew hit 20 to win the contest.


title: Harmon Killebrew

text: After his seven-triple season, his speed began to decrease and he could no longer regularly score triples due to pulling his quadriceps during the 1962 season. Killebrew moved to left field, where he started off the season slowly. He hit under .200 in both April and June, and because of this Killebrew was not selected to play in either 1962 All-Star Game, the last season he was not named an All-Star before 1972. On July 18 in a game against the Cleveland Indians, Killebrew and Bob Allison became the first teammates since 1890 to hit grand slams in the same inning as the Twins scored 11 runs in the first. Over the course of the season, Killebrew hit 48 home runs, 126 RBIs, and had 107 walks, all career highs at the time. No one else in the AL managed even 40 home runs and he also led the league in RBIs. Killebrew's 48 home runs also broke the franchise record for the second year in a row. Not all his stats were positive; Killebrew's batting average dropped from .288 in 1961 to .243 and he struck out a career-worst 142 times, leading the AL.


title: Harmon Killebrew

text: Killebrew's efforts were rewarded in 1963 when he agreed to a contract for about $40,000 ($ today). He started the season off slowly, and he missed the second half of April and early May due to a right knee injury that was slow to heal. Killebrew continued his hitting prowess for the Twins upon his return, and at one point led them on a six-game winning streak. On September 21, Killebrew hit three home runs in a game for the only time in his career in the first game of a doubleheader against the Boston Red Sox. Killebrew finished the season with a .258 batting average, 45 home runs, and 96 RBI, and led the league in home runs and slugging percentage (.555). He had surgery on his troublesome right knee after the season ended.


title: Harmon Killebrew

text: Having played left field for the previous three years with a below-average throwing arm, the additional complication of Killebrew's knee surgery necessitated a move to the infield. For the remainder of his career, he played only 19 games in the outfield. He finished the 1964 season with a .270 batting average, 49 home runs, and 111 RBI; he led the AL in home runs for the third consecutive year.


title: Harmon Killebrew

text: The Twins finally won the American League pennant during the 1965 season. On July 11, the day before the All-Star break, the defending AL champion Yankees had a one-run lead over the Twins going into the bottom of the 9th inning, but Killebrew hit a two-run home run for the win. Two days later, Killebrew started the All-Star Game at his home field, Metropolitan Stadium, and hit a game-tying two-run home run, erasing what had been a 5–0 National League lead. Elected to play first base on his fifth All-Star team, Killebrew became the first player in All-Star game history to be elected at three different positions, having previously been selected to play third base (1959 and 1961) and left field (1963 and 1964).


title: Harmon Killebrew

text: Killebrew drove in the tying or winning run seven times in 1965 before suffering an injury on August 2. During a game against the Orioles, Twins third baseman Rich Rollins made a poor throw to first and while trying to save the play, Killebrew collided with the runner and dislocated his elbow, putting him out of action until mid-September. Despite his absence, the Twins had a win–loss record of 28–19 and even extended their first place lead. Killebrew ended the regular season with 25 home runs and 75 RBI, his lowest numbers in a full season due to the injury. In the 1965 World Series against the Los Angeles Dodgers, Killebrew and Zoilo Versalles led the Twins with .286 batting averages, and Killebrew hit a home run off Don Drysdale in Game 4. Minnesota was shut out in three games and the Dodgers won the series in seven.


title: Harmon Killebrew

text: At the start of the 1966 season, Killebrew hit few home runs; halfway through May, he had hit only two, his lowest total at that point of a season since 1960, when he had missed the first two months of the season. He later increased his tally to 39 and finished the season with a .281 batting average and 110 RBIs. He led the AL with 103 walks and finished 4th in Most Valuable Player Award (MVP) voting after Frank Robinson, Brooks Robinson, and Boog Powell of the American League leading Baltimore Orioles.


title: Harmon Killebrew

text: During the 1967 season Killebrew hit the then longest home run recorded at Metropolitan Stadium, a June 3 shot off Lew Burdette in the 4th inning that landed in the second deck of the bleachers. The Twins, led by Killebrew, were in the pennant race throughout the season, and had a one-game lead as the final two games of the season began against the Boston Red Sox. Having to win only once to clinch the pennant, Killebrew hit a home run in the first game and recorded two hits in each game, but Boston won twice and Minnesota finished in a second place tie with the Detroit Tigers. Killebrew finished the season with a .269 batting average and 113 RBIs, tied AL Triple Crown winner Carl Yastrzemski with 44 home runs, and led the league with 131 walks. He also finished a distant second in MVP voting to the Boston star.


title: Harmon Killebrew

text: In April 1968 Killebrew served as a prosecution witness in a case where his name was being used to fraudulently sell stocks in Idaho. The baseball season proved unsuccessful for Killebrew, whose batting average barely passed .200 most of the year; after a strong start, he hit below .200 in both May and June and his average stood at .204 with 13 home runs going into the all-star break. Even so, he was selected as the starting first baseman in the All-Star Game and Killebrew said that, owing to his poor start, he was "surprised" and "embarrassed" by the selection. During the third inning of the game he stretched for a ball thrown by shortstop Jim Fregosi, his foot slipped, and he did the splits, rupturing his left medial hamstring. He was carried from the field by a stretcher. At the time, the injury was considered career-threatening, but after missing about six weeks, he returned to limited action in September.


title: Harmon Killebrew

text: After enduring seven months of rehabilitation for his injury, Killebrew remained in pain but rebounded to have his best season in 1969. On July 5, Killebrew set a career-high with six RBIs in a game against the Oakland Athletics. On September 7 he topped that mark with a three-run homer and a grand slam in the first two innings, leading the team to another defeat of the Athletics . Killebrew led the best offense in the league and rookie manager Billy Martin's Twins won the new American League West division as a result.


title: Harmon Killebrew

text: For the season, Killebrew set career highs in RBIs, runs, walks and on-base percentage, tied his career high with 49 home runs, and even registered eight of his 19 career stolen bases, en route to winning his only Most Valuable Player Award. Playing in all 162 games, he led the majors in home runs and RBI (140), while leading the AL in on-base percentage (.427), walks (145) and intentional walks (20). As of 2021, Killebrew's home run, RBI, and walk totals from 1969 remain team records, and his 145 walks are tied for the 20th highest single season total in MLB history and 7th highest for a right-handed batter. In the 1969 American League Championship Series, the Baltimore Orioles used their pitching staff, the best in the league, to defeat Minnesota and win the series three games to none. Baltimore avoided Killebrew by walking him six times in the three games to avoid pitching to him, which was as many times as they walked the rest of the Twins team.


title: Harmon Killebrew

text: After his MVP season, Killebrew signed a new contract with the Twins worth $90,000 ($ today). He was set to lead a team that had undergone a lot of change; Killebrew was one of only four Twins remaining from the 1965 pennant-winning club. He spent most of the season's first half continuing his success, and found Baltimore's Brooks Robinson rivalling him for the third base spot during the All-Star voting process; the two were neck-and-neck throughout. He continued his success through the second half of the year, and at season's end had hit 41 home runs with 113 RBIs and finished third in MVP voting behind teammate and runner-up Tony Oliva and Baltimore's Boog Powell. In a rematch of the previous season the Twins again faced Powell and the Orioles in the 1970 American League Championship Series. Killebrew upped his performance and hit two home runs in three games, but Minnesota was again swept.


title: Harmon Killebrew

text: Killebrew reached 40 home runs in a season for the final time in 1970 and also made his last appearance in the postseason. His contract continued to grow in value though, and before the 1971 season began he was awarded the first $100,000 ($ today) contract in Twins history. Killebrew appeared in his last All-Star Game in 1971, hitting a two-run home run off Ferguson Jenkins to provide the margin of victory for the AL. He finished the season with a .254 batting average, 114 walks, 119 RBI, the latter two of which led the league, and 28 home runs. Killebrew hit his 498th home run on June 22, 1971, but a sprained right toe made his run to milestone number 500 a slow one. He hit number 499 more than a month later and finally hit number 500 off a Mike Cuellar slow curveball in the first inning of an August 10 home game; at the time, he was the 10th player in history to hit 500 home runs. He then wasted no time in hitting number 501, knocking a Cuellar fastball over the fences later in the same game.


title: Harmon Killebrew

text: In 1972, Killebrew showed signs of slowing down. He missed his first All-Star Game since 1962, but instead of expressing disappointment in his streak ending, he noted that Twins shortstop Danny Thompson should have had the opportunity to play instead; Thompson mentioned the same thing about Killebrew. Despite not making the team, Killebrew's home run total continued to climb, and by the end of July he had Jimmie Foxx and Mickey Mantle's career marks in his sights; he went on to pass both in August. Killebrew finished the season with a .231 batting average, 26 home runs, and 74 RBIs. There were questions about Killebrew's health as the 1973 season began, as he had surgery twice during the offseason to fix leg problems. He played through the first half of the season, but an injury to his left knee on June 25 sidelined him. A month later, the injury had not cleared up, and he underwent surgery to remove some torn cartilage; he did not return to the lineup until mid-September. Killebrew played in only 69 games that season, hitting five home runs.


title: Harmon Killebrew

text: Fully recovered for the 1974 season, Killebrew made his mark early on, hitting two home runs in a May 5 match against the Detroit Tigers; the second was career home run number 550. In his honor, the Twins held Harmon Killebrew Day in August, when it was announced that they would retire his number; Killebrew responded by leading the Twins to a 5–4 victory over the Orioles. He finished the season with a .222 batting average, 13 home runs, and 54 RBIs. In December 1974, he was given the option of staying with the Twins as a coach and batting instructor, managing the AAA Tacoma Twins, or being released. He chose to be released, ending his 21-season tenure with the Twins.


title: Harmon Killebrew

text: On January 24, 1975, eight days after getting his release from the Twins, Killebrew signed a one-year contract with the Kansas City Royals. During his return to Minnesota in early May, the Twins formally retired his No. 3 jersey. In that game, Killebrew hit a home run against his former teammates and received a standing ovation from the crowd. In 106 games with the Royals, he had a batting average of .199, 14 home runs, and 44 RBIs. At the end of the season, the Royals released Killebrew. In March 1976, he formally announced his retirement and said he would become an announcer and color commentator for Twins games. At the time of his retirement, he was fifth all-time on the home run list.


title: Harmon Killebrew

text: Killebrew was first eligible for the Hall of Fame in 1981 and received 239 votes, or 59.6% of the vote; 75% of the vote is required for induction. While he did hit 573 home runs (5th all-time when he left the game), he amassed a relatively low hit total (2086), given the years he played, combined with a high number of strikeouts (1699), and a .256 batting average. In 1982, Killebrew received 59.3% of the vote, taking a backseat to Hank Aaron and Frank Robinson, who made it in their first year of eligibility. After receiving 71.9% of the vote in 1983, Killebrew said not getting in that year was more difficult to accept than the previous two times, and asked "Why do the writers feel there only has to be a certain number inducted each time?" In 1984, Killebrew received 83.1% of the vote and was elected to the Hall in his fourth year of eligibility, joining Luis Aparicio and Don Drysdale as electees.


title: Harmon Killebrew

text: Killebrew hit 573 home runs (12th all time), drove in 1,584 RBIs and had 1,559 (15th all time) bases on balls during his career. He is also the all-time home run record holder among players born in Idaho; Vance Law is second. He also finished with the record of having the most plate appearances (9,831) in his career without a sacrifice hit (since broken by Frank Thomas with 10,074 plate appearances).


title: Harmon Killebrew

text: Reggie Jackson once said, "If Harmon Killebrew isn't the league's best player, I've never seen one." The street along the south side of the Mall of America, the former site of Metropolitan Stadium, in Bloomington, Minnesota, is named "Killebrew Drive" in his honor. Banners that hung above the Metrodome's outfield upper deck, resembling baseball cards, showed the retired numbers: Killebrew (3), Rod Carew (29), Tony Oliva (6), Kent Hrbek (14) and Kirby Puckett (34). In 1999, he was ranked 69th on "The Sporting News" list of the 100 Greatest Baseball Players and nominated as a finalist for Major League Baseball's All-Century Team. When the Twins moved to Target Field in 2010, Gate 3 on the southeast (center field) side of the stadium was named in his honor. There are also corresponding gates for the team's other retired numbers. Killebrew Canyon at Heavenly Mountain Resort is also named after Killebrew, who skied the resort's outer limits after his retirement from baseball.


title: Harmon Killebrew

text: Despite rumors that Killebrew is the player depicted in the Major League Baseball logo, according to the creator, Jerry Dior, it was not patterned after any specific player. Killebrew is the model for the Major League Baseball Players Alumni Association, an organization he helped found in 1982.


title: Harmon Killebrew

text: Killebrew was known as an all-around gentleman during his playing career. "He's one of the greatest of all time." He was even noted as being kind to the umpires:


title: Harmon Killebrew

text: Killebrew was known for his quick hands and exceptional upper-body strength, demonstrated by frequent "tape measure" home runs he hit in the prime of his career. Killebrew said his first home run in the Majors was his favorite, coming off Billy Hoeft at Griffith Stadium. He said of it, "Frank House was the catcher. When I came to the plate, he said, 'Kid, we're going to throw you a fastball.' I didn't know whether to believe him or not. I hit it out. It was one of the longest home runs I ever hit. As I crossed the plate, House said, 'That's the last time I ever tell you what pitch is coming.'"


title: Harmon Killebrew

text: On August 3, 1962, he was the first batter ever to hit a baseball over the left field roof at Tiger Stadium, a seldom-reached target as contrasted with the old ballpark's smaller right field area. Only three others accomplished this feat during the next 37 seasons before the stadium closed. On May 24, 1964, Harmon hit the longest measured homer at Baltimore's Memorial Stadium, to deep left center. The ball landed in the far reaches of the bleachers. The only player to hit one completely out of the Orioles' stadium was Frank Robinson in 1966; his blast was reported as about , or about less than Killebrew's. On June 3, 1967, Killebrew hit a home run, the longest measured home run ever hit at Metropolitan Stadium and, as of 2022, the longest in Twins history. That event is commemorated at the Mall of America in Bloomington, which includes a plaque marking home plate, and one red-painted seat from the Met which was placed at the location and elevation of the landing spot of the home run. Target Field had a statue of a Gold Glove outside Gate 34 that was exactly from Target Field's home plate. It was moved to another location after the Twins created the Gate 34 experience.


title: Harmon Killebrew

text: Following his retirement, Killebrew was a television broadcaster for the Twins at WTCN TV from 1976 to 1978, the Oakland Athletics from 1979 to 1982, the California Angels in 1983 and back with Minnesota from 1984 to 1988. While with Oakland, he also served as a major- and minor-league hitting instructor. In the late 1980s, Killebrew had financial problems. In July 1988, his house went into foreclosure and, in 1989, the "Minneapolis Star Tribune" reported that he had fallen $700,000 into debt. He also divorced his first wife of more than 30 years, Elaine Killebrew "née" Roberts, whom he had married in 1955. Soon after, Killebrew's health failed. In May 1990, he was rushed to the hospital with a collapsed lung and damaged esophagus. Together with a subsequent abscess and staph infection, Killebrew endured three surgeries and nearly died. He used a wheelchair for some time post-surgery. By December 1990, his health had improved and he married Nita Patten.


title: Harmon Killebrew

text: Killebrew was involved in a Boise, Idaho insurance and securities business. He moved to Scottsdale, Arizona, in 1990, where he chaired the Harmon Killebrew Foundation, which he created in 1998. Killebrew founded the Danny Thompson Memorial Golf Tournament, now titled the Killebrew-Thompson Memorial in 1977 with former Idaho congressman Ralph Harding, which is played annually in late August in Sun Valley, Idaho, and has donated more than $15.6 million to leukemia and cancer research. Thompson was a Twins teammate who continued his major league career while suffering from leukemia; he died in December 1976 at the age of 29.


title: Harmon Killebrew

text: Despite his nicknames and style of play, Killebrew was considered by his colleagues to be a quiet, kind man. While still an active major leaguer, Killebrew became a member of the Church of Jesus Christ of Latter-day Saints, and never smoked or drank. He was once asked in an interview what hobbies he had, to which he replied, "Just washing the dishes, I guess."


title: Harmon Killebrew

text: On December 29, 2010, Killebrew announced that he had been diagnosed with esophageal cancer and started treatment. On May 13, 2011, a Minnesota Twins press release reported he was ceasing treatment and entering hospice care, because his illness had progressed beyond his doctors' expectation of cure. To honor Killebrew, the Twins wore their 1961 throwback alternate jerseys at home for the remainder of the 2011 season; he was also honored by the Washington Nationals, who hung a jersey with Killebrew's name and number 3 in their home dugout. Killebrew died on May 17, 2011, at his home in Scottsdale at the age of 74. He was interred at Riverside Cemetery in Payette, Idaho.