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 ;
	(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]

^ "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.
^ ^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.
^ 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.
^ 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.
^ 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.