CHEBI:5971 - irinotecan hydrochloride (anhydrous)

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ChEBI Name irinotecan hydrochloride (anhydrous)
ChEBI ID CHEBI:5971
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C33H39ClN4O6
Net Charge 0
Average Mass 623.140
Monoisotopic Mass 622.25581
InChI InChI=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
InChIKey GURKHSYORGJETM-WAQYZQTGSA-N
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
Roles Classification
Biological Role(s): 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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 irinotecan hydrochloride hydrate (CHEBI:90881) has part irinotecan hydrochloride (anhydrous) (CHEBI:5971)
IUPAC Names
(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
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
Synonyms Sources
7-Ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxy camptothecin hydrochloride ChemIDplus
Camptothecin 11 hydrochloride ChemIDplus
CPT 11 ChemIDplus
CPT-11 ChemIDplus
Irinotecan HCl ChemIDplus
Irinotecan hydrochloride ChemIDplus
irinotecan monohydrochloride ChEBI
U 101440E ChemIDplus
Manual Xrefs Databases
DB00762 DrugBank
Irinotecan Wikipedia
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Registry Numbers Types Sources
100286-90-6 CAS Registry Number ChemIDplus
4837793 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
12 January 2016