Structure via PubChem · Public domain (PubChem)
topotecan
Sign in to saveAlso known as Hycamtin®, SK-S-104864-A, 9-[(dimethylamino)methyl]-10-hydroxy-(4S)-camptothecin, Topotecanum, 9-[(dimethylamino)Methyl]-10-hydroxy-(4S)-camptothecin, Topotecane
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.
Chemical data
- Formula
- C23H23N3O5
- Molecular weight
- 421.4 g/mol
- IUPAC name
- (19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
- SMILES
- CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O
- InChIKey
- UCFGDBYHRUNTLO-QHCPKHFHSA-N
- XLogP
- 0.5
- Polar surface area
- 103 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
3,947 papersvia PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 421.164
- Manufacturer
- Pfizer
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₃H₂₃N₃O₅
- Commons category
- Topotecan
- canonical SMILES
- CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=C(C5=C4)CN(C)C)O)O
- isomeric SMILES
- CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=C(C5=C4)CN(C)C)O)O
- World Health Organisation international non-proprietary name
- topotecan
- legal status (medicine)
- boxed warning
Sources (9)
via Wikidata · CC0
~6 min read
Encyclopedic overview
9 sectionsContents
- Uses
- Experimental uses
- Angelman's syndrome
- Mechanism of action
- Side effects
- Generic versions
- References
- Sources
- External links
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.
Excerpted from Wikipedia’s “topotecan” article, available under the CC BY-SA 4.0 licence.