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CHEBI:63617 - pergolide

ChEBI IDCHEBI:63617
ChEBI Namepergolide
Stars
DefinitionA diamine that is ergoline in which the β-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is replaced by a propyl group. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used as the mesylate salt in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.
Secondary ChEBI IDCHEBI:8020
Last Modified22 February 2017
DownloadsMolfile
FormulaC19H26N2S
Net Charge0
Average Mass314.498
Monoisotopic Mass314.18167
SMILES[H][C@@]12Cc3cnc4cccc(c34)[C@@]1([H])C[C@@H](CSC)CN2CCC
InChIInChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,18-/m1/s1
InChIKeyYEHCICAEULNIGD-MZMPZRCHSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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.
ChEBI Ontology
Outgoing Relation(s)
pergolide (CHEBI:63617) has role antiparkinson drug (CHEBI:48407)
pergolide (CHEBI:63617) has role dopamine agonist (CHEBI:51065)
pergolide (CHEBI:63617) is a diamine (CHEBI:23666)
pergolide (CHEBI:63617) is a methyl sulfide (CHEBI:86315)
pergolide (CHEBI:63617) is a organic heterotetracyclic compound (CHEBI:38163)
pergolide (CHEBI:63617) is conjugate base of pergolide(1+) (CHEBI:63706)
Incoming Relation(s)
pergolide(1+) (CHEBI:63706) is conjugate acid of pergolide (CHEBI:63617)
IUPAC Name 
(8β)-8-[(methylsulfanyl)methyl]-6-propylergoline
INNs  Source
pergolidumChemIDplus
pergolideChemIDplus
pergolidaChemIDplus
Manual XrefsDatabases
C07425KEGG COMPOUND
D08339KEGG DRUG
US4166182Patent
DB01186DrugBank
PergolideWikipedia
HMDB0015317HMDB
LSM-3352LINCS
2105DrugCentral
Registry NumbersSources
Reaxys:5091461Reaxys
CAS:66104-22-1KEGG COMPOUND
CAS:66104-22-1ChemIDplus
Citations