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CHEBI:90881 - irinotecan hydrochloride hydrate

Default Structure
ChEBI IDCHEBI:90881
ChEBI Nameirinotecan hydrochloride hydrate
Stars
DefinitionA 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.
Last Modified12 January 2016
SubmitterSteve
DownloadsMolfile
FormulaC33H38N4O6.3H2O.HCl
Net Charge0
Average Mass677.195
Monoisotopic Mass676.28751
SMILESCCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC.Cl.O.O.O
InChIInChI=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
InChIKeyKLEAIHJJLUAXIQ-JDRGBKBRSA-N
Wikipedia
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 5.99.1.2 (DNA topoisomerase) inhibitor  A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) 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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
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 5.99.1.2 (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)
IUPAC Names 
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)
(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)
Synonyms  Source
CPT 11KEGG DRUG
CPT-11KEGG DRUG
Irinotecan hydrochlorideKEGG DRUG
irinotecan hydrochloride trihydrateChEBI
irinotecan monohydrochloride trihydrateChEBI
U-101,440EChemIDplus
Brand Names  Source
CamptosarDrugBank
ONIVYDEChEBI
Manual XrefsDatabases
D01061KEGG DRUG
DB00762DrugBank
IrinotecanWikipedia
Registry NumbersSources
Reaxys:4838283Reaxys
CAS:136572-09-3KEGG DRUG
CAS:136572-09-3ChemIDplus
Citations