Irinotecan hydrochloride
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Irinotecan hydrochloride
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CAS No:
100286-90-6
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Formula:
C33H38N4O6.ClH
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Chemical Name:
Irinotecan hydrochloride
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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 (1:1);[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,(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;1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline,[1,4′-bipiperidine]-1′-carboxylic acid deriv.;CPT 11;Camptothecin 11;7-Ethyl-10-[[4-(1-piperidyl)-1-piperidyl]carbonyloxy]camptothecin hydrochloride;Camptothecin 11 hydrochloride;Irinotecan hydrochloride;U 101440E;Topotecin;Campto;Camptosar;Topotesin;(19S)-10,19-Diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0[2,11].0[4,9].0[15,20]]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate hydrochloride;111348-33-5
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CAS No:
Description
Yellow Crystalline PowderChEBI: A hydrochloride obtained by combining irinotecan with one molar equivalent of hydrochloric acid. Used (in the form of its trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancr as 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.lrinotecan hydrochlor
Irinotecan hydrochloride (anhydrous) is a hydrochloride obtained by combining irinotecan with one molar equivalent of hydrochloric acid. Used (in the form of its 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 EC 5.99.1.2 (DNA topoisomerase) inhibitor, an antineoplastic agent, an apoptosis inducer and a prodrug. It contains an irinotecan(1+).|Irinotecan and topotecan are semisynthetic derivatives of the plant alkaloid camptothecin and are used as antineoplastic agents in the therapy of colorectal, ovarian and non-small cell lung cancer. Both irinotecan and topotecan are associated with an appreciable rate of serum enzyme elevations during therapy, and irinotecan has been implicated in causing steatohepatitis when given as cyclic anticancer therapy.|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 Basic Attributes
623.14
622.255798
1308068-626-2
06X131E4OE
759878|616348
DTXSID6045953
29399990
Characteristics
113
4.76890
Yellow crystalline powder
250-256°C (dec.)
257 °C
482ºC
67.7 ° (C=1, H2O)
soluble in DMSO at 100mg/ml. soluble in water at 25mg/ml with warming;soluble in DMF at approximately 20mg/ml. Sparingly soluble in aqueous buffers.
Refrigerator
1.31E-32mmHg at 25°C
Safety Information
NONH for all modes of transport
3
22
DW1060750
Xn
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory.
Toxicity
Chemotherapy with irinotecan and topotecan in combination with other agents is associated with serum enzyme elevations in up 15% of patients depending upon the dose, other agents used, the frequency of monitoring and degree of elevation that is reported. The ALT elevations are usually asymptomatic and transient and may resolve without dose modification. Marked elevations occur in 1% to 4% of patients, but rarely require dose modification. Genetic variants in hepatic transporters and metabolic enzymes have been associated with predisposition to irinotecan toxicity, including OATP 1B1 (SLC01B1), UGT1A1 and CYP 3A4. However, the major toxicities of irinotecan are hematologic and diarrhea, and liver test elevations are rare causes of drug interruption or dose modification.
Drug Information
Drug: Irinotecanhydrochloride|Drug: Folfiri|Drug: Folfiri-bevacizumab|Drug: Folfiri-cetuximab|Drug: Folfirinox|Drug: Xeliri
Irinotecan and topotecan are semisynthetic derivatives of the plant alkaloid camptothecin and are used as antineoplastic agents in the therapy of colorectal, ovarian and non-small cell lung cancer. Both irinotecan and topotecan are associated with an appreciable rate of serum enzyme elevations during therapy, and irinotecan has been implicated in causing steatohepatitis when given as cyclic anticancer therapy.
Antineoplastic Agents
Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)
7 Ethyl 10 hydroxycamptothecin
Irinotecan hydrochloride Use and Manufacturing
A DNA topoisomerase inhibitor
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:623.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:622.2558127
Monoisotopic Mass:622.2558127
Topological Polar Surface Area:113
Heavy Atom Count:44
Complexity:1200
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Irinotecan hydrochloride is a derivative of camptothecin that specifically acts on topoisomerase I. It binds to the topoisomerase I-DNA complex, preventing the reconnection of single-stranded DNA and causing damage to double-stranded DNA. Its active metabolite SN-38 has an inhibitory effect on topoisomerase I that is 1000 times greater than that of irinotecan hydrochloride, but its exact contribution is still unknown.
Registered Holders
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Fermion Oy
Active
Finland
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SCINOPHARM TAIWAN, LTD.
Active
Taiwan, China
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Yuanda Wuyao (Jiangsu) Pharmaceutical Co., Ltd.
Active
China
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