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CHEBI:80630 - irinotecan

ChEBI IDCHEBI:80630
ChEBI Nameirinotecan
Stars
DefinitionA member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt 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 Modified22 February 2017
DownloadsMolfile
FormulaC33H38N4O6
Net Charge0
Average Mass586.689
Monoisotopic Mass586.27913
SMILESCCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
InChIInChI=1S/C33H38N4O6/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/t33-/m0/s1
InChIKeyUWKQSNNFCGGAFS-XIFFEERXSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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:
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 (CHEBI:80630) has functional parent SN-38 (CHEBI:8988)
irinotecan (CHEBI:80630) has role antineoplastic agent (CHEBI:35610)
irinotecan (CHEBI:80630) has role apoptosis inducer (CHEBI:68495)
irinotecan (CHEBI:80630) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
irinotecan (CHEBI:80630) has role prodrug (CHEBI:50266)
irinotecan (CHEBI:80630) is a N-acylpiperidine (CHEBI:48591)
irinotecan (CHEBI:80630) is a carbamate ester (CHEBI:23003)
irinotecan (CHEBI:80630) is a pyranoindolizinoquinoline (CHEBI:48626)
irinotecan (CHEBI:80630) is a ring assembly (CHEBI:36820)
irinotecan (CHEBI:80630) is a tertiary alcohol (CHEBI:26878)
irinotecan (CHEBI:80630) is a tertiary amino compound (CHEBI:50996)
irinotecan (CHEBI:80630) is a δ-lactone (CHEBI:18946)
irinotecan (CHEBI:80630) is conjugate base of irinotecan(1+) (CHEBI:90895)
Incoming Relation(s)
irinotecan(1+) (CHEBI:90895) is conjugate acid of irinotecan (CHEBI:80630)
IUPAC Name 
(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
INNs  Source
irinotecanChemIDplus
irinotecanumChemIDplus
Synonyms  Source
(+)-IrinotecanChemIDplus
Irinotecan lactoneChemIDplus
HSDB 7607ChemIDplus
Irinotecan mylanChemIDplus
Irinophore CChemIDplus
Manual XrefsDatabases
D08086KEGG DRUG
CP0PDBeChem
C16641KEGG COMPOUND
DB00762DrugBank
HMDB0014900HMDB
IrinotecanWikipedia
LSM-2167LINCS
1482DrugCentral
Registry NumbersSources
Reaxys:4839096Reaxys
CAS:97682-44-5KEGG COMPOUND
CAS:97682-44-5ChemIDplus
Citations