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The Drug Ontology
| Preferred Name | irinotecan | |
| Synonyms |
Irinotecan mylan Irinophore C (+)-Irinotecan irinotecanum Irinotecan lactone HSDB 7607 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 |
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| 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 |
|
| alternative label |
Irinotecan mylan Irinophore C (+)-Irinotecan irinotecanum Irinotecan lactone HSDB 7607 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
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|
| charge |
0
|
|
| database_cross_reference |
Drug_Central:1482 PMID:26487578 PMID:26739304 PMID:26081596 PMID:26352218 KEGG:C16641 LINCS:LSM-2167 Reaxys:4839096 KEGG:D08086 HMDB:HMDB0014900 Wikipedia:Irinotecan CAS:97682-44-5 PMID:26541586 DrugBank:DB00762 PMID:26580826 PDBeChem:CP0 PMID:26574999 PMID:26503200 PMID:26526067 PMID:26381420
|
|
| 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.
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|
| formula |
C33H38N4O6
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|
| 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 mylan Irinophore C (+)-Irinotecan irinotecanum Irinotecan lactone HSDB 7607 irinotecan
|
|
| has_RxCUI |
51499
|
|
| 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
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|
| notation |
CHEBI:80630
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|
| prefLabel |
irinotecan
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|
| 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
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|
| 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 |
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