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Etoposide ball-and-stick.png
Systematic (IUPAC) name
Clinical data
Trade names Etopophos
AHFS/ monograph
MedlinePlus a684055
  • AU: D
  • US: D (Evidence of risk)
Legal status
Routes of
Oral, intravenous
Pharmacokinetic data
Bioavailability Highly variable, 25 to 75%
Protein binding 97%
Metabolism Hepatic (CYP3A4 involved)
Excretion Renal and fecal
CAS Number 33419-42-0 YesY
ATC code L01CB01
PubChem CID 36462
DrugBank DB00773 YesY
ChemSpider 33510 YesY
KEGG D00125 YesY
Synonyms VP-16; VP-16-213
Chemical data
Formula C29H32O13
Molar mass 588.557 g/mol
Physical data
Melting point 243.5 °C (470.3 °F)

Etoposide or VP-16 (trade name Etopophos) is a cytotoxic anticancer drug which belongs to the topoisomerase inhibitor drug class. It is used in form of its salt etoposide phosphate.


Medical uses[edit]



It is given intravenously (IV) or orally in capsule form. If the drug is given IV, it must be done slowly over a 30- to 60-minute period because it can lower blood pressure as it is being administered. Blood pressure is checked often during infusing, with the speed of administration adjusted accordingly.

Side effects[edit]

Common are:

Less common are:

When given with warfarin, it may cause bleeding.[3]


Mechanism of action[edit]

Etoposide forms a ternary complex with DNA and the topoisomerase II enzyme (which aids in DNA unwinding), prevents re-ligation of the DNA strands, and by doing so causes DNA strands to break.[4] Cancer cells rely on this enzyme more than healthy cells, since they divide more rapidly. Therefore, this causes errors in DNA synthesis and promotes apoptosis of the cancer cell.[2][5]

Physical and chemical properties[edit]

An illustration of the wild mandrake, showing part of the rhizome (at bottom)

Etoposide is a semisynthetic derivative of podophyllotoxin from the rhizome of the wild mandrake (Podophyllum peltatum). More specifically, it is a glycoside of podophyllotoxin with a D-glucose derivative. It is chemically similar to the anti-cancer drug teniposide, being distinguished only by a methyl rest where teniposide has a thienyl.[6] Both these compounds have been developed with the aim of creating less toxic derivatives of podophyllotoxin.[7]

The substance is a white to yellow-brown, crystalline powder. It is soluble in organic solvents.[7]


Etoposide was first synthesized in 1966 and U.S. Food and Drug Administration approval was granted in 1983.[2]

The nickname VP-16 likely comes from a compounding of the last name of the chemists who performed early work on the drug (von Wartburg and von Kuhn) and podophyllotoxin.[8] Another scientist who was integral in the development of podophyllotoxin-based chemotherapeutics was the medical pharmacologist Hartmann F. Stähelin.


  6. ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 894–5. ISBN 3-8047-1763-2. 
  7. ^ a b Dinnendahl, V, Fricke, U, ed. (2015). Arzneistoff-Profile (in German) 4 (28 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3. 

External links[edit]