Irinotecan is a pyranoindolizinoquinoline carbamate ester formed by the 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]quinoline-3,14-dione. It is used as its hydrochloride salt trihydrate in combination with fluorouracil and leucovorin for treating metastatic pancreatic adenocarcinoma after gemcitabine-based therapy failure. Irinotecan is hydrolyzed to its active metabolite SN-38, which is ~1000 times more active. It functions as an apoptosis inducer, DNA topoisomerase inhibitor, antineoplastic agent, and prodrug. It is classified as a pyranoindolizinoquinoline, N-acylpiperidine, carbamate ester, tertiary alcohol, tertiary amino compound, delta-lactone, and ring assembly. It is functionally related to SN-38 and is the conjugate base of irinotecan(1+).
