Structure via PubChem · Public domain (PubChem)
etoposide
Sign in to saveAlso known as (-)-etoposide, Etopophos®, Toposar®, trans-etoposide, VePesid®, VP 16-213, VP-16, 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5aH)-one
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.
Chemical data
- Formula
- C29H32O13
- Molecular weight
- 588.6 g/mol
- IUPAC name
- (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
- SMILES
- C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
- InChIKey
- VJJPUSNTGOMMGY-MRVIYFEKSA-N
- XLogP
- 0.6
- Polar surface area
- 161 Ų
- H-bond donors
- 3
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
30,378 papers- Etoposide (VP-16-213).Cancer treatment reviews · 1979
- Etoposide: an update.Clinical pharmacy · 1989
- Etoposide pharmacology.Seminars in oncology · 1992
- Oral etoposide.Drug intelligence & clinical pharmacy · 1988
- Etoposide: discovery and medicinal chemistry.Current medicinal chemistry · 2004
via PubMed
Wikidata facts
- Mass
- 588.184
Show 5 more facts
- chemical formula
- C₂₉H₃₂O₁₃
- canonical SMILES
- CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
- isomeric SMILES
- C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
- World Health Organisation international non-proprietary name
- etoposide
- Commons category
- Etoposide
Sources (7)
via Wikidata · CC0
~5 min read
Article
9 sectionsContents
- Medical uses
- Administration
- Side effects
- Pharmacology
- Mechanism of action
- Chemistry
- History
- References
- External links
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.