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CHEBI:3286 - cabergoline

Default Structure
ChEBI IDCHEBI:3286
ChEBI Namecabergoline
Stars
DefinitionAn N-acylurea that is (8R)-ergoline-8-carboxamide in which the hydrogen attached to the piperidine nitrogen (position 6) is substituted by an allyl group and the hydrogens attached to the carboxamide nitrogen are substituted by a 3-(dimethylamino)propyl group and an N-ethylcarbamoyl group. A dopamine D2 receptor agonist, cabergoline is used in the management of Parkinson's disease and of disorders associated with hyperprolactinaemia.
Last Modified22 February 2017
DownloadsMolfile
FormulaC26H37N5O2
Net Charge0
Average Mass451.615
Monoisotopic Mass451.29473
SMILES[H][C@@]12Cc3cnc4cccc(c34)[C@@]1([H])C[C@@H](C(=O)N(CCCN(C)C)C(=O)NCC)CN2CC=C
InChIInChI=1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
InChIKeyKORNTPPJEAJQIU-KJXAQDMKSA-N
Wikipedia
Roles Classification
Biological Role:
dopamine agonist  A drug that binds to and activates dopamine receptors.
Applications:
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
dopamine agonist  A drug that binds to and activates dopamine receptors.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
cabergoline (CHEBI:3286) has role antineoplastic agent (CHEBI:35610)
cabergoline (CHEBI:3286) has role antiparkinson drug (CHEBI:48407)
cabergoline (CHEBI:3286) has role dopamine agonist (CHEBI:51065)
cabergoline (CHEBI:3286) is a N-acylurea (CHEBI:74266)
IUPAC Name 
(8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide
INNs  Source
cabergolinaChemIDplus
cabergolineChemIDplus
cabergolinumChemIDplus
Synonyms  Source
1-((6-allylergolin-8β-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylureaChemIDplus
1-[(6-allylergoline-8β-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylureaChEBI
1-ethyl-3-(3'-dimethylamionpropyl)-2-(6'-allylergoline-8'β-carbonyl)ureaChEBI
(8R)-6-allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergoline-8-carboxamideChEBI
(8β)-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-ergoline-8-carboxamideChEBI
CabergolineKEGG COMPOUND
Manual XrefsDatabases
1830VSDB
460DrugCentral
BE888243Patent
C08187KEGG COMPOUND
CabergolineWikipedia
D00987KEGG DRUG
DB00248DrugBank
HMDB0014393HMDB
LSM-3939LINCS
US4526892Patent
Registry NumbersSources
Beilstein:6020775Beilstein
CAS:81409-90-7ChemIDplus
CAS:81409-90-7KEGG COMPOUND
Citations