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irinotecan |
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CHEBI:80630 |
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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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This entity has been manually annotated by the ChEBI Team.
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Molfile
XML
SDF
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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 |
UWKQSNNFCGGAFS-XIFFEERXSA-N |
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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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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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.
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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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View more via ChEBI Ontology
(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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irinotecan
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ChemIDplus
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irinotecanum
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ChemIDplus
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(+)-Irinotecan
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ChemIDplus
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HSDB 7607
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ChemIDplus
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Irinophore C
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ChemIDplus
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Irinotecan lactone
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ChemIDplus
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Irinotecan mylan
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ChemIDplus
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1482
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DrugCentral
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C16641
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KEGG COMPOUND
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CP0
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PDBeChem
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D08086
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KEGG DRUG
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DB00762
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DrugBank
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HMDB0014900
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HMDB
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Irinotecan
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Wikipedia
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LSM-2167
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LINCS
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View more database links |
4839096
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Reaxys Registry Number
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Reaxys
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97682-44-5
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CAS Registry Number
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KEGG COMPOUND
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97682-44-5
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CAS Registry Number
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ChemIDplus
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26081596
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PubMed citation
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Europe PMC
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26352218
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PubMed citation
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Europe PMC
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26381420
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PubMed citation
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Europe PMC
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26487578
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PubMed citation
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Europe PMC
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26503200
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PubMed citation
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Europe PMC
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26526067
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PubMed citation
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Europe PMC
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26541586
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PubMed citation
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Europe PMC
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26574999
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PubMed citation
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Europe PMC
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26580826
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PubMed citation
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Europe PMC
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26739304
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PubMed citation
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Europe PMC
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