Preferred Name

irinotecan

Synonyms

(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

irinotecan

Irinotecan lactone

(+)-Irinotecan

Irinophore C

HSDB 7607

Irinotecan mylan

irinotecanum

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

http://purl.obolibrary.org/obo/CHEBI_8988

has role

http://purl.obolibrary.org/obo/CHEBI_35610

http://purl.obolibrary.org/obo/CHEBI_50276

http://purl.obolibrary.org/obo/CHEBI_68495

http://purl.obolibrary.org/obo/CHEBI_50266

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

http://purl.obolibrary.org/obo/chebi#3_STAR

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

http://purl.obolibrary.org/obo/CHEBI_90895

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

http://purl.obolibrary.org/obo/CHEBI_50996

http://purl.obolibrary.org/obo/CHEBI_36820

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

http://purl.obolibrary.org/obo/CHEBI_50996

http://purl.obolibrary.org/obo/CHEBI_36820

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Delete Mapping To Ontology Source
http://purl.obolibrary.org/obo/CHEBI_80630 OBA SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 EFO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 PDRO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 FIDEO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 BERO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 DRON SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 OBA SAME_URI
http://purl.obolibrary.org/obo/CHEBI_80630 OBA LOOM
http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C62040 NCIT LOOM
http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C62040 ROO LOOM
http://sbmi.uth.tmc.edu/ontology/ochv#C0123931 OCHV LOOM
http://purl.bioontology.org/ontology/NDFRT/N0000022032 NDFRT LOOM
http://www.drugbank.ca/drugs/DB00762 FTC LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 EFO LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 PDRO LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 FIDEO LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 BERO LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 DRON LOOM
http://purl.obolibrary.org/obo/CHEBI_80630 OBA LOOM
https://go.drugbank.com/drugs/DB00762 MDM LOOM
http://purl.bioontology.org/ontology/RXNORM/51499 RXNORM LOOM
http://purl.bioontology.org/ontology/MESH/D000077146 MESH LOOM
http://www.co-ode.org/ontologies/galen#Irinotecan GALEN LOOM
http://www.phoc.org.cn/pmo/class/PMO_00026193 PMAPP-PMO LOOM
http://purl.bioontology.org/ontology/ATC/L01CE02 ATC LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#C051890 RH-MESH LOOM
http://purl.bioontology.org/ontology/CSP/4009-0014 CRISP LOOM
http://purl.bioontology.org/ontology/VANDF/4024027 VANDF LOOM
http://purl.bioontology.org/ontology/NDDF/005262 NDDF LOOM
http://sbmi.uth.tmc.edu/ontology/ochv#16325 OCHV LOOM
http://purl.obolibrary.org/obo/NCIT_C62040 BERO LOOM
http://purl.obolibrary.org/obo/dinto_DB00762 DINTO LOOM
http://purl.jp/bio/4/id/200906060658722270 IOBC LOOM
http://purl.bioontology.org/ontology/SNOMEDCT/372538008 SNOMEDCT LOOM
http://stirdf.jst.go.jp/id/200907064751838008 IOBC LOOM