Irinotecan
Title: Irinotecan
CAS Registry Number: 97682-44-5
CAS Name: [1,4¢-Bipiperidine]-1¢-carboxylic acid (4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3¢,4¢:6,7]indolizino[1,2-b]quinolin-9-yl ester
Additional Names: 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin; (+)-7-ethyl-10-hydroxycamptothecine 10-[1,4¢-bipiperidine]-1¢-carboxylate; (+)-(4S)-4,11-diethyl-4-hydroxy-9-[(4-piperidinopiperidino)carbonyloxy]-1H-pyrano[3¢,4¢:6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
Molecular Formula: C33H38N4O6
Molecular Weight: 586.68
Percent Composition: C 67.56%, H 6.53%, N 9.55%, O 16.36%
Literature References: DNA topoisomerase I inhibitor. Semisynthetic derivative of camptothecin, q.v.; de-esterified in vivo to the active metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38). Prepn: JP Kokai 85 19790; T. Miyasaka et al., US 4604463 (1985, 1986 both to Yakult Honsha); S. Sawada et al., Chem. Pharm. Bull. 39, 1446 (1991). Antitumor activity and toxicity data: T. Kunimoto et al., Cancer Res. 47, 5944 (1987). Mechanism of action study: Y. Kawato et al., ibid. 51, 4187 (1991). Clinical trial in colorectal cancer: J. Y. Douillard et al., Lancet 355, 1041 (2000). Review of pharmacology and clinical experience: N. Masuda et al., Crit. Rev. Oncol. Hematol. 24, 3-26 (1996); S. O'Reilly, E. K. Rowinsky, ibid. 47-70; of clinical toxicity: K. Seiter, Expert Opin. Drug Safety 4, 45-53 (2005).
Properties: Pale yellow powder, mp 222-223°.
Melting point: mp 222-223°
 
Derivative Type: Hydrochloride trihydrate
CAS Registry Number: 136572-09-3; 100286-90-6 (hydrochloride)
Manufacturers' Codes: CPT-11; DQ-2805
Trademarks: Campto (Sanofi-Aventis); Camptosar (Pharmacia & Upjohn)
Molecular Formula: C33H38N4O6.HCl.3H2O
Molecular Weight: 677.18
Percent Composition: C 58.53%, H 6.70%, N 8.27%, O 21.26%, Cl 5.24%
Properties: Slightly pale yellow needles or crystalline powder from water, mp 256.5°. [a]D20 +67.7° (c = 1 in water). uv max (ethanol): 221, 254, 359, 372 nm (e 53800, 36600, 26200, 25300). Slightly sol in water and organic solvents. pH of 2% aqueous soln = 4. LD50 in mice (mg/kg): 177.5 i.p.; 765.3 orally (Kunimoto).
Melting point: mp 256.5°
Optical Rotation: [a]D20 +67.7° (c = 1 in water)
Absorption maximum: uv max (ethanol): 221, 254, 359, 372 nm (e 53800, 36600, 26200, 25300)
Toxicity data: LD50 in mice (mg/kg): 177.5 i.p.; 765.3 orally (Kunimoto)
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Camptothecin Derivatives; Topoisomerase I Inhibitor.

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