CHEBI:80630 - irinotecan

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ChEBI Name irinotecan
ChEBI ID CHEBI:80630
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C33H38N4O6
Net Charge 0
Average Mass 586.679
Monoisotopic Mass 586.279
InChI InChI=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
InChIKey UWKQSNNFCGGAFS-XIFFEERXSA-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
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
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.
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ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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 conjugate base of irinotecan(1+) (CHEBI:90895)
Incoming 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 Sources
irinotecan ChemIDplus
irinotecanum ChemIDplus
Synonyms Sources
(+)-Irinotecan ChemIDplus
HSDB 7607 ChemIDplus
Irinophore C ChemIDplus
Irinotecan lactone ChemIDplus
Irinotecan mylan ChemIDplus
Manual Xrefs Databases
1482 DrugCentral
C16641 KEGG COMPOUND
CP0 PDBeChem
D08086 KEGG DRUG
DB00762 DrugBank
HMDB0014900 HMDB
Irinotecan Wikipedia
LSM-2167 LINCS
View more database links
Registry Numbers Types Sources
4839096 Reaxys Registry Number Reaxys
97682-44-5 CAS Registry Number KEGG COMPOUND
97682-44-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
26081596 PubMed citation Europe PMC
26352218 PubMed citation Europe PMC
26381420 PubMed citation Europe PMC
26487578 PubMed citation Europe PMC
26503200 PubMed citation Europe PMC
26526067 PubMed citation Europe PMC
26541586 PubMed citation Europe PMC
26574999 PubMed citation Europe PMC
26580826 PubMed citation Europe PMC
26739304 PubMed citation Europe PMC
Last Modified
22 February 2017