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Topotecan information


Topotecan
Clinical data
Trade namesHycamtin, Potactasol
AHFS/Drugs.comMonograph
MedlinePlusa610007
License data
  • EU EMA: by INN
  • US DailyMed: Topotecan
Pregnancy
category
  • AU: D
Routes of
administration
Intravenous infusion, by mouth (capsules)
ATC code
  • L01CE01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability31.4 % in humans[2][3]
Protein binding35%
MetabolismLiver
Elimination half-life2–3 hours
ExcretionKidney
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 ☒N 119413-54-6 (hydrochloride)
PubChem CID
  • 60700
IUPHAR/BPS
  • 7101
DrugBank
  • DB01030 checkY
ChemSpider
  • 54705 checkY
UNII
  • 7M7YKX2N15
KEGG
  • D08618 checkY
  • D02168
ChEMBL
  • ChEMBL84 checkY
CompTox Dashboard (EPA)
  • DTXSID3042685 Edit this at Wikidata
ECHA InfoCard100.213.372 Edit this at Wikidata
Chemical and physical data
FormulaC23H23N3O5
Molar mass421.453 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 checkY
  • Key:UCFGDBYHRUNTLO-QHCPKHFHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 October 15, 2007, it became the first topoisomerase I inhibitor for oral use.[4]

  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. ^ 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.
  3. ^ 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.
  4. ^ Delgado, Justine L.; Hsieh, Chao-Ming; Chan, Nei-Li; Hiasa, Hiroshi (2018-01-31). "Topoisomerases as anticancer targets". Biochemical Journal. 475 (2): 373–398. doi:10.1042/BCJ20160583. ISSN 0264-6021. PMC 6110615. PMID 29363591.

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