Topotecan

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.

Topotecan
Clinical data
Trade namesHycamtin, Potactasol
AHFS/Drugs.comMonograph
MedlinePlusa610007
License data
Pregnancy
category
  • AU: D
Routes of
administration
Intravenous infusion, by mouth (capsules)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability31.4 % in humans
Protein binding35%
MetabolismLiver
Elimination half-life2–3 hours
ExcretionKidney
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.213.372
Chemical and physical data
FormulaC23H23N3O5
Molar mass421.453 g·mol−1
3D model (JSmol)
  • O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)c(c(O)cc5)CN(C)C
  • 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 Y
  • Key:UCFGDBYHRUNTLO-QHCPKHFHSA-N Y
 NY (what is this?)  (verify)

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

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