136572-09-3 Usage
Description
Irinotecan (136572-09-3) is a semi-synthetic derivative of camptothecin (Cat.# 10-1041) that is an FDA approved anticancer drug. It is a prodrug that is converted by tissue esterases to 7-ethyl-10-hydroxycamptothecin (SN-38, Cat.# 10-2425), a potent inhibitor of DNA topoisomerase I.1,2 Although irinotecan is also a topoisomerase inhibitor, SN-38 is approximately 1000 times as potent in purified enzyme studies. In vitro cytotoxicity assays show much greater variability in potency between the two (2-2000 fold).3
Chemical Properties
White powder
Uses
Different sources of media describe the Uses of 136572-09-3 differently. You can refer to the following data:
1. A DNA topoisomerase inhibitor.
2. Irinotecan Hydrochloride Trihydrate is a DNA topoisomerase inhibitor.
Definition
ChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used 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.
Brand name
Camptosar (Pharmacia &Upjohn)
.
Hazard
Moderately toxic by ingestion.
References
1) Kunimoto et al. (1987) Antitumor activity of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin, a novel water-soluble derivative of camptothecin against murine tumors; Cancer Res., 47 5944
2) Mathijssen et al., (2002) Pharmacology of topoisomerase I inhibitors irinotecan (CPT-11) and topotecan; Curr. Cancer Drug Targets, 253 5892
3) Pfizer drug insert
Check Digit Verification of cas no
The CAS Registry Mumber 136572-09-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,6,5,7 and 2 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 136572-09:
(8*1)+(7*3)+(6*6)+(5*5)+(4*7)+(3*2)+(2*0)+(1*9)=133
133 % 10 = 3
So 136572-09-3 is a valid CAS Registry Number.
InChI:InChI=1/C33H38N4O6.ClH/c1-3-22-23-9-8-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)16-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2;/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;1H/t33-;/m0./s1
136572-09-3Relevant articles and documents
Synthesis method of irinotecan hydrochloride
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Paragraph 0026-0028, (2021/07/17)
The invention discloses a synthesis method of irinotecan hydrochloride, belonging to the technical field of compound preparation. The synthesis method comprises the following steps: (1) in the presence of an organic solvent, alkali and a catalyst, subjecting 7-ethyl-10-hydroxycamptothecin to full reactionwith 4-piperidinyl piperidinecarbonyl chloride at room temperature, quenching the reaction by using a 5% sodium bicarbonate solution, and separating out an organic phase; and (2) adding normal hexane into the organic phase obtained in the step (1) for crystallization, performing filtering, adding an organic solvent and concentrated hydrochloric acid into a filter cake, conducting reacting to obtain a crude irinotecan hydrochloride product, and purifying the crude irinotecan hydrochloride product to obtain irinotecan hydrochloride. According to the invention, carbonate is used as a catalyst, charging is convenient, and generated products are carbon dioxide and water and are friendly to a system; and in addition, n-hexane is adopted as a reverse solvent for crystallization, yield is high, post-treatment is convenient, and industrial mass production is facilitated.
