Camptothecin

Camptothecin

Clinical data
ATC code	none
Identifiers
IUPAC name (S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b] quinoline-3,14-(4H,12H)-dione
CAS Number	7689-03-4 Y
PubChem CID	2538
DrugBank	DB04690 Y
ChemSpider	22775 Y
UNII	XT3Z54Z28A
KEGG	C01897 Y
ChEBI	CHEBI:27656 Y
ChEMBL	CHEMBL65 Y
ECHA InfoCard	100.113.172
Chemical and physical data
Formula	C20H16N2O4
Molar mass	348.352 g/mol
3D model (Jmol)	Interactive image
Melting point	275 to 277 °C (527 to 531 °F)
SMILES O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)cccc5
InChI InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1 Y Key:VSJKWCGYPAHWDS-FQEVSTJZSA-N Y

Camptothecin (CPT) is a cytotoxic quinoline alkaloid which inhibits the DNA enzyme topoisomerase I (topo I). It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata (Camptotheca, Happy tree), a tree native to China used as a cancer treatment in Traditional Chinese Medicine. CPT showed remarkable anticancer activity in preliminary clinical trials but also low solubility and (high) adverse drug reaction. Because of these disadvantages, synthetic and medicinal chemists have developed numerous syntheses of Camptothecin and various derivatives to increase the benefits of the chemical, with good results. Two CPT analogues have been approved and are used in cancer chemotherapy today, topotecan and irinotecan.

CPT has a planar pentacyclic ring structure, that includes a pyrrolo[3,4-β]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). Its planar structure is thought to be one of the most important factors in topoisomerase inhibition.