irinotecan

Term ID

CHEBI:80630

Synonyms

• (+)-Irinotecan
• (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
• HSDB 7607
• Irinophore C
• irinotecan
• Irinotecan lactone
• Irinotecan mylan
• irinotecanum

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.

References

• CAS:97682-44-5
• DrugBank:DB00762
• Drug_Central:1482
• HMDB:HMDB0014900
• KEGG:C16641
• KEGG:D08086
• LINCS:LSM-2167
• PDBeChem:CP0
• PMID:26081596
• PMID:26352218
• PMID:26381420
• PMID:26487578
• PMID:26503200
• PMID:26526067
• PMID:26541586
• PMID:26574999
• PMID:26580826
• PMID:26739304
• Reaxys:4839096
• Wikipedia:Irinotecan

Ontology

ChEBI  ( EBI )