Etoposide

Etoposide
Clinical data
Pronunciation	/ˌɛtoʊˈpoʊsaɪd/
Trade names	Etopophos, Toposar, Vepesid, others
Other names	VP-16; VP-16-213
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy; category	AU: D;
Routes of; administration	By mouth, intravenous
ATC code	L01CB01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	Highly variable, 25 to 75%
Protein binding	97%
Metabolism	Liver (CYP3A4 involved)
Elimination half-life	Oral: 6 h., IV: 6-12 h., IV in children: 3 h.
Excretion	Kidney and fecal
Identifiers
	IUPAC name 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside], 4' -(dihydrogen phosphate);
CAS Number	33419-42-0 ;
PubChem CID	36462;
IUPHAR/BPS	6815;
DrugBank	DB00773 ;
ChemSpider	33510 ;
UNII	6PLQ3CP4P3;
KEGG	D00125 ; as salt: D04107 ;
ChEBI	CHEBI:4911 ;
ChEMBL	ChEMBL44657 ;
CompTox Dashboard (EPA)	DTXSID5023035 ;
ECHA InfoCard	100.046.812
Chemical and physical data
Formula	C29H32O13
Molar mass	588.562 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	243.5 °C (470.3 °F)
	SMILES C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@@H]3c4cc5c(cc4[C@H]([C@@H]6[C@@H]3COC6=O)c7cc(c(c(c7)OC)O)OC)OCO5)O)O;
	InChI InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1 ; Key:VJJPUSNTGOMMGY-MRVIYFEKSA-N ;
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Etoposide, sold under the brand name Vepesid among others, is a chemotherapy medication used for the treatments of a number of types of cancer including testicular cancer, lung cancer, lymphoma, leukemia, neuroblastoma, and ovarian cancer. It is also used for hemophagocytic lymphohistiocytosis. It is used by mouth or injection into a vein.

Side effects are very common. They can include low blood cell counts, vomiting, loss of appetite, diarrhea, hair loss, and fever. Other severe side effects include allergic reactions and low blood pressure. Use during pregnancy will likely harm the fetus. Etoposide is in the topoisomerase inhibitor family of medication. It is believed to work by damaging DNA.

Etoposide was approved for medical use in the United States in 1983. It is on the World Health Organization's List of Essential Medicines.

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