136572-09-3 Usage
Description
Irinotecan hydrochloride trihydrate, also known as Onivyde, is a semi-synthetic derivative of camptothecin, an FDA-approved anticancer drug. It is a prodrug that is converted by tissue esterases to 7-ethyl-10-hydroxycamptothecin (SN-38), a potent inhibitor of DNA topoisomerase I. Irinotecan hydrochloride trihydrate is a white powder and is marketed under the brand name Camptosar by Pharmacia & Upjohn.
Uses
Used in Anticancer Applications:
Irinotecan hydrochloride trihydrate is used as a DNA topoisomerase inhibitor for the treatment of various types of cancer. It is particularly effective against solid malignancies and is used in combination with other chemotherapeutic agents to enhance their efficacy and overcome drug resistance.
Used in Pancreatic Cancer Treatment:
Irinotecan hydrochloride trihydrate is used as a component of a combination therapy 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 approximately 1000 times more active.
Used in Drug Delivery Systems:
Irinotecan hydrochloride trihydrate can be incorporated into various drug delivery systems to improve its bioavailability, delivery, and therapeutic outcomes. These systems may include organic and metallic nanoparticles as carriers, aiming to enhance the drug's effectiveness against cancer cells and minimize side effects.
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.
