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CHEBI:5971 - irinotecan hydrochloride (anhydrous)

ChEBI IDCHEBI:5971
ChEBI Nameirinotecan hydrochloride (anhydrous)
Stars
DefinitionA 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.
Last Modified12 January 2016
DownloadsMolfile
FormulaC33H38N4O6.HCl
Net Charge0
Average Mass623.150
Monoisotopic Mass622.25581
SMILESCCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC.Cl
InChIInChI=1S/C33H38N4O6.ClH/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/t33-;/m0./s1
InChIKeyGURKHSYORGJETM-WAQYZQTGSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) has part irinotecan(1+) (CHEBI:90895)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) has role antineoplastic agent (CHEBI:35610)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) has role apoptosis inducer (CHEBI:68495)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) has role prodrug (CHEBI:50266)
irinotecan hydrochloride (anhydrous) (CHEBI:5971) is a hydrochloride (CHEBI:36807)
Incoming Relation(s)
irinotecan hydrochloride hydrate (CHEBI:90881) has part irinotecan hydrochloride (anhydrous) (CHEBI:5971)
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
(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
Synonyms  Source
Irinotecan hydrochlorideChemIDplus
irinotecan monohydrochlorideChEBI
7-Ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxy camptothecin hydrochlorideChemIDplus
CPT-11ChemIDplus
U 101440EChemIDplus
CPT 11ChemIDplus
Manual XrefsDatabases
DB00762DrugBank
IrinotecanWikipedia
Registry NumbersSources
Reaxys:4837793Reaxys
CAS:100286-90-6ChemIDplus
Citations