Etoposide

Etoposide
Clinical data


Pronunciation	/ˌɛtoʊˈpoʊsaɪd/
Trade names	Etopophos, Toposar, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	by mouth, intravenous
ATC code	L01CB01 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Highly variable, 25 to 75%
Protein binding	97%
Metabolism	Liver (CYP3A4 involved)
Biological 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)
Synonyms	VP-16; VP-16-213
CAS Number	33419-42-0^Y
PubChem (CID)	36462
IUPHAR/BPS	6815
DrugBank	DB00773^Y
ChemSpider	33510^Y
UNII	6PLQ3CP4P3^Y
KEGG	D00125^Y
ChEBI	CHEBI:4911^Y
ChEMBL	CHEMBL44657^Y
ECHA InfoCard	100.046.812
Chemical and physical data
Formula	C₂₉H₃₂O₁₃
Molar mass	588.557 g/mol
3D model (Jmol)	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^Y Key:VJJPUSNTGOMMGY-MRVIYFEKSA-N^Y

Etoposide, sold under the brand name Etopophos among others, is a chemotherapy medication used for the treatments of a number of types of cancer. This includes testicular cancer, lung cancer, lymphoma, leukemia, neuroblastoma, and ovarian cancer. 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 baby. 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 3.24 to 5.18 USD per 100 mg vial. In the United Kingdom this costs the NHS about 12.15 pounds as of 2015.

Etoposide is used as a form of chemotherapy for cancers such as Kaposi’s sarcoma, Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, nonlymphocytic leukemia, and glioblastoma multiforme. It is often given in combination with other drugs (such as bleomycin in treating testicular cancer). It is also sometimes used in a conditioning regimen prior to a bone marrow or blood stem cell transplant.

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