Topotecan

Topotecan
Clinical data
Trade names	Hycamtin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a610007
License data	US DailyMed: Topotecan;
Pregnancy; category	AU: D; ;
Routes of; administration	Intravenous infusion, by mouth
ATC code	L01CE01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	31.4 % in humans
Protein binding	35%
Metabolism	Liver
Elimination half-life	2–3 hours
Excretion	Kidney
Identifiers
	IUPAC name (S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione monohydrochloride;
CAS Number	123948-87-8 119413-54-6 (hydrochloride);
PubChem CID	60700;
IUPHAR/BPS	7101;
DrugBank	DB01030 ;
ChemSpider	54705 ;
UNII	7M7YKX2N15;
KEGG	D08618 ; D02168;
ChEMBL	ChEMBL84 ;
CompTox Dashboard (EPA)	DTXSID3042685 ;
ECHA InfoCard	100.213.372
Chemical and physical data
Formula	C23H23N3O5
Molar mass	421.453 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)c(c(O)cc5)CN(C)C;
	InChI InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1 ; Key:UCFGDBYHRUNTLO-QHCPKHFHSA-N ;
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Topotecan, sold under the brand name Hycamtin among others, is a chemotherapeutic agent medication that is a topoisomerase inhibitor. It is a synthetic, water-soluble analog of the natural chemical compound camptothecin. It is used in the form of its hydrochloride salt to treat ovarian cancer, lung cancer and other cancer types.

After GlaxoSmithKline received final FDA approval for topotecan on 15 October 2007, it became the first topoisomerase I inhibitor for oral use.^[7]

^ "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 October 2023.
^ "Hycamtin- topotecan capsule". DailyMed. 7 July 2022. Retrieved 26 August 2024.
^ "Hycamtin- topotecan hydrochloride injection, powder, lyophilized, for solution". DailyMed. 7 July 2022. Retrieved 26 August 2024.
^ "Hycamtin EPAR". European Medicines Agency (EMA). 12 November 1996. Retrieved 26 August 2024.
^ Léger F, Loos WJ, Bugat R, Mathijssen RH, Goffinet M, Verweij J, et al. (December 2004). "Mechanism-based models for topotecan-induced neutropenia". Clinical Pharmacology and Therapeutics. 76 (6): 567–78. doi:10.1016/j.clpt.2004.08.008. PMID 15592328. S2CID 37527965.
^ Gelderblom H, Loos WJ, Sissung TM, Burger H, Nooter K, Soepenberg O, et al. (July 2004). "Effect of ABCG2 genotype and mRNA expression on the bioavailability of topotecan". Journal of Clinical Oncology. 22 (14 suppl): 2015. doi:10.1200/jco.2004.22.90140.2015. PMID 28015603.
^ Delgado JL, Hsieh CM, Chan NL, Hiasa H (January 2018). "Topoisomerases as anticancer targets". The Biochemical Journal. 475 (2): 373–398. doi:10.1042/BCJ20160583. PMC 6110615. PMID 29363591.