Link to this page
Chemical Entities of Biological Interest Ontology
| Preferred Name | irinotecan | |
| Synonyms |
irinotecan Irinotecan lactone (+)-Irinotecan Irinophore C HSDB 7607 Irinotecan mylan irinotecanum (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 |
|
| Definitions |
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. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_80630 |
|
| charge |
0
|
|
| database_cross_reference |
PMID:26503200 PMID:26081596 PMID:26541586 KEGG:D08086 PMID:26580826 CAS:97682-44-5 PMID:26487578 DrugBank:DB00762 PMID:26739304 PMID:26381420 PDBeChem:CP0 PMID:26574999 LINCS:LSM-2167 Wikipedia:Irinotecan KEGG:C16641 PMID:26526067 HMDB:HMDB0014900 Reaxys:4839096 Drug_Central:1482 PMID:26352218
|
|
| 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.
|
|
| formula |
C33H38N4O6
|
|
| has functional parent | ||
| has role |
http://purl.obolibrary.org/obo/CHEBI_35610 http://purl.obolibrary.org/obo/CHEBI_50276 |
|
| has_exact_synonym |
(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
|
|
| has_obo_namespace |
chebi_ontology
|
|
| has_related_synonym |
irinotecan Irinotecan lactone (+)-Irinotecan Irinophore C HSDB 7607 Irinotecan mylan irinotecanum
|
|
| id |
CHEBI:80630
|
|
| in_subset | ||
| 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
|
|
| is conjugate base of | ||
| label |
irinotecan
|
|
| mass |
586.679
|
|
| monoisotopicmass |
586.27913
|
|
| notation |
CHEBI:80630
|
|
| prefLabel |
irinotecan
|
|
| 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
|
|
| treeView |
http://purl.obolibrary.org/obo/CHEBI_48591 http://purl.obolibrary.org/obo/CHEBI_18946 http://purl.obolibrary.org/obo/CHEBI_48626 http://purl.obolibrary.org/obo/CHEBI_23003 http://purl.obolibrary.org/obo/CHEBI_26878 |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_48591 http://purl.obolibrary.org/obo/CHEBI_18946 http://purl.obolibrary.org/obo/CHEBI_48626 http://purl.obolibrary.org/obo/CHEBI_23003 http://purl.obolibrary.org/obo/CHEBI_26878 |
| Delete | Subject | Author | Type | Created |
|---|---|---|---|---|
| No notes to display |