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IRINOTECAN

IUPAC Name: [(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

Symbol: IR

Molecular Formula: C33H38N4O6

Molecular weight: 586.7 g/mol

CAS No: 97682-44-5

ATC Code: L01CE02

Drug Class: Anti-Cancer

General Properties:

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 apoptosis inducer, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an antineoplastic agent and a prodrug. It is a pyranoindolizinoquinoline, a N-acylpiperidine, a carbamate ester, a tertiary alcohol, a tertiary amino compound, a delta-lactone and a ring assembly. It is functionally related to a SN-38. It is a conjugate base of an irinotecan(1+).

Irinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. It is a derivative of camptothecin that inhibits the action of topoisomerase I. Irinotecan prevents religation of the DNA strand by binding to topoisomerase I-DNA complex, and causes double-strand DNA breakage and cell death. It is a derivative of camptothecin.

Irinotecan is a Topoisomerase Inhibitor. The mechanism of action of irinotecan is as a Topoisomerase Inhibitor.

Indication:

Irinotecan is a medication used to manage and treat a variety of solid tumors. It is in the DNA topoisomerase I inhibitor class of drugs. Also known as CPT-11, irinotecan is used adjunctively with other therapeutic agents against colorectal cancer as a first- or second-line treatment.

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