CHEBI:90881 - irinotecan hydrochloride hydrate

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ChEBI Name irinotecan hydrochloride hydrate
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C33H45ClN4O9
Net Charge 0
Average Mass 677.186
Monoisotopic Mass 676.28751
InChI InChI=1S/C33H38N4O6.ClH.3H2O/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(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;3*1H2/t33-;;;;/m0..../s1
SMILES C1(=CC=C2C(=C1)C(=C3C(=N2)C=4N(C3)C(C5=C(C4)[C@](C(OC5)=O)(CC)O)=O)CC)OC(=O)N6CCC(CC6)N7CCCCC7.Cl.O.O.O
Roles Classification
Biological Role(s): EC (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing irinotecan hydrochloride hydrate (CHEBI:90881) has part irinotecan hydrochloride (anhydrous) (CHEBI:5971)
irinotecan hydrochloride hydrate (CHEBI:90881) has role antineoplastic agent (CHEBI:35610)
irinotecan hydrochloride hydrate (CHEBI:90881) has role apoptosis inducer (CHEBI:68495)
irinotecan hydrochloride hydrate (CHEBI:90881) has role EC (DNA topoisomerase) inhibitor (CHEBI:50276)
irinotecan hydrochloride hydrate (CHEBI:90881) has role prodrug (CHEBI:50266)
irinotecan hydrochloride hydrate (CHEBI:90881) is a hydrate (CHEBI:35505)
(4S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate hydrochloride—water (1/3)
1-[1-({[(4S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl]oxy}carbonyl)piperidin-4-yl]piperidin-1-ium chloride—water (1/3)
Synonyms Sources
Irinotecan hydrochloride KEGG DRUG
irinotecan hydrochloride trihydrate ChEBI
irinotecan monohydrochloride trihydrate ChEBI
U-101,440E ChemIDplus
Brand Names Sources
Camptosar DrugBank
Manual Xrefs Databases
DB00762 DrugBank
Irinotecan Wikipedia
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Registry Numbers Types Sources
136572-09-3 CAS Registry Number KEGG DRUG
136572-09-3 CAS Registry Number ChemIDplus
4838283 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
23984532 PubMed citation Europe PMC
24190390 PubMed citation Europe PMC
24424522 PubMed citation Europe PMC
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26352218 PubMed citation Europe PMC
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26706406 PubMed citation Europe PMC
Last Modified
12 January 2016