Etoposide

Etoposide
Clinical data
Pronunciation/ˌɛtoʊˈpoʊsaɪd/
Trade namesEtopophos, Toposar, Vepesid, others
Other namesVP-16; VP-16-213
AHFS/Drugs.comMonograph
MedlinePlusa684055
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHighly variable, 25 to 75%
Protein binding97%
MetabolismLiver (CYP3A4 involved)
Elimination half-lifeOral: 6 h., IV: 6-12 h., IV in children: 3 h.
ExcretionKidney and fecal
Identifiers
  • 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside], 4' -(dihydrogen phosphate)
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.812 Edit this at Wikidata
Chemical and physical data
FormulaC29H32O13
Molar mass588.562 g·mol−1
3D model (JSmol)
Melting point243.5 °C (470.3 °F)
  • 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=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 checkY
  • Key:VJJPUSNTGOMMGY-MRVIYFEKSA-N checkY
  (verify)

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.[2] It is also used for hemophagocytic lymphohistiocytosis.[3] It is used by mouth or injection into a vein.[2]

Side effects are very common.[2] They can include low blood cell counts, vomiting, loss of appetite, diarrhea, hair loss, and fever.[2] Other severe side effects include allergic reactions and low blood pressure.[2][4] Use during pregnancy will likely harm the fetus.[2] Etoposide is in the topoisomerase inhibitor family of medication.[2] It is believed to work by damaging DNA.[2]

Etoposide was approved for medical use in the United States in 1983.[2] It is on the World Health Organization's List of Essential Medicines.[5]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c d e f g h i "Etoposide". The American Society of Health-System Pharmacists. Archived from the original on 31 March 2016. Retrieved 8 December 2016.
  3. ^ Yildiz H, Van Den Neste E, Defour JP, Danse E, Yombi JC (January 2020). "Adult haemophagocytic lymphohistiocytosis: a Review". QJM. 115 (4): 205–213. doi:10.1093/qjmed/hcaa011. PMID 31943120.
  4. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 227. hdl:10665/44053. ISBN 9789241547659.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.