کامپتوتسین

Also known as (+)-camptothecin, (+)-camptothecine, (s)-(+)-camptothecin, (s)-camptothecin, 20(S)-Camptothecin, 21,22-Secocamptothecin-21-oic acid lactone, Camptothecine, D-camptothecin

Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark of Camptotheca acuminata (喜树 "Happy tree"), a tree native to China used in traditional Chinese medicine. It has been used clinically in China for the treatment of gastrointestinal tumors. CPT showed anticancer activity in preliminary clinical trials, especially against breast, ovarian, colon, lung, and stomach cancers. However, it has low solubility and adverse effects have been reported when used

Key facts

Drug.N: 2
Drug.O: 4
Drug.C: 20
Drug.H: 16
Drug.Watchedfields: changed
Drug.verifiedrevid: 443672460
Drug.IUPAC_name: (S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
Drug.image: camptothecin.svg
Drug.image_class: skin-invert-image
Drug.CAS_number: 7689-03-4
Drug.ATC_prefix: none
Drug.PubChem: 2538
Drug.DrugBank: DB04690
Drug.ChemSpiderID: 22775
Drug.UNII: XT3Z54Z28A
Drug.KEGG: C01897
Drug.ChEBI: 27656
Drug.ChEMBL: 65

via Wikipedia infobox

Chemical data

Formula: C20H16N2O4
Molecular weight: 348.4 g/mol
IUPAC name: (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
InChIKey: VSJKWCGYPAHWDS-FQEVSTJZSA-N
XLogP: 1
Polar surface area: 79.7 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0