irinotecan

irinotecan

[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-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)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate

PubChem CID: 60838

Irinotecan is a member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. It has a role as an antineoplastic agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It is a delta-lactone, a carbamate ester, a tertiary alcohol, a ring assembly, a N-acylpiperidine, a pyranoindolizinoquinoline and a tertiary amino compound. It is functionally related to a SN-38. It is a conjugate base of an irinotecan(1+).

2D Structure

Properties

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Synonyms(20)