Irinotecan hydrochloride trihydrate
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Irinotecan hydrochloride trihydrate
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CAS No:
136572-09-3
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Formula:
C33H38N4O6.ClH.3H2O
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Chemical Name:
Irinotecan hydrochloride trihydrate
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Synonyms:
[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,hydrochloride,hydrate (1:1:3);[1,4′-Bipiperidine]-1′-carboxylic acid,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,monohydrochloride,trihydrate,(S)-;[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,monohydrochloride,trihydrate;1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline,[1,4′-bipiperidine]-1′-carboxylic acid deriv.;Irinotecan hydrochloride hydrate;Irinotecan hydrochloride trihydrate;Onivyde;Onivyde pegylated liposomal
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CAS No:
Description
White powderChEBI: 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.
Irinotecan hydrochloride hydrate is 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. It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an antineoplastic agent, an apoptosis inducer and a prodrug. It contains an irinotecan hydrochloride (anhydrous).|Irinotecan Hydrochloride is the hydrochloride salt of a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. Irinotecan, a prodrug, is converted to a biologically active metabolite 7-ethyl-10-hydroxy-camptothecin (SN-38) by a carboxylesterase-converting enzyme. One thousand-fold more potent than its parent compound irinotecan, SN-38 inhibits topoisomerase I activity by stabilizing the cleavable complex between topoisomerase I and DNA, resulting in DNA breaks that inhibit DNA replication and trigger apoptotic cell death. Because ongoing DNA synthesis is necessary for irinotecan to exert its cytotoxic effects, it is classified as an S-phase-specific agent.|A semisynthetic camptothecin derivative that inhibits DNA TOPOISOMERASE I to prevent nucleic acid synthesis during S PHASE. It is used as an antineoplastic agent for the treatment of COLORECTAL NEOPLASMS and PANCREATIC NEOPLASMS.
Irinotecan hydrochloride trihydrate Basic Attributes
677.18
676.287537
1308068-626-2
042LAQ1IIS
C1381
L01CE02
29349990
Safety Information
22
20/21-22
DW1060750
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
H302
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 15 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Treatment of metastatic adenocarcinoma of the pancreas, in combination with 5 fluorouracil (5 FU) and leucovorin (LV), in adult patients who have progressed following gemcitabine based therapy.|Drug: Irinotecanhydrochloride|Drug: Irinotecan-hydrochloride-liposome
Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)
7 Ethyl 10 hydroxycamptothecin
Irinotecan hydrochloride trihydrate Use and Manufacturing
Irinotecan HCl (4.8 g), water (30 ml), ethanol (10 ml) and 5 percent HCl (0.3 ml) were charged. The mixture was heated to 75-80 °C and stirred until all dissolved. The solution was cooled to 65 Irinotecan HCl (4.8 g), water (30 ml), ethanol (10 ml) and 5 percent HCl (0.3 ml) were charged. The mixture was heated to 75-80 °C and stirred until all dissolved. The solution was cooled to 65
A DNA topoisomerase inhibitor.
Human drugs -> Orphan -> Onivyde pegylated liposomal (previously known as Onivyde) -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:677.2
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:5
Exact Mass:676.2875067
Monoisotopic Mass:676.2875067
Topological Polar Surface Area:116
Heavy Atom Count:47
Complexity:1200
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:5
Compound Is Canonicalized:Yes
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Irinotecan hydrochloride trihydrate
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