CHEBI:63617 - pergolide

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ChEBI Name pergolide
ChEBI ID CHEBI:63617
Definition A 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D1 and D2 agonist properties, it is used as the mesylate salt in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:8020
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Formula C19H26N2S
Net Charge 0
Average Mass 314.48800
Monoisotopic Mass 314.182
InChI InChI=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
InChIKey YEHCICAEULNIGD-MZMPZRCHSA-N
SMILES [H][C@@]12Cc3c[nH]c4cccc(c34)[C@@]1([H])C[C@@H](CSC)CN2CCC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): dopamine agonist
A drug that binds to and activates dopamine receptors.
Application(s): antiparkinson drug
A drug used in the treatment of Parkinson's disease.
dopamine agonist
A drug that binds to and activates dopamine receptors.
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ChEBI Ontology
Outgoing 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 pergolide(1+) (CHEBI:63706) is conjugate acid of pergolide (CHEBI:63617)
IUPAC Name
(8β)-8-[(methylsulfanyl)methyl]-6-propylergoline
INNs Sources
pergolida ChemIDplus
pergolide ChemIDplus
pergolidum ChemIDplus
Manual Xrefs Databases
2105 DrugCentral
C07425 KEGG COMPOUND
D08339 KEGG DRUG
DB01186 DrugBank
HMDB0015317 HMDB
LSM-3352 LINCS
Pergolide Wikipedia
US4166182 Patent
View more database links
Registry Numbers Types Sources
5091461 Reaxys Registry Number Reaxys
66104-22-1 CAS Registry Number KEGG COMPOUND
66104-22-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11852289 PubMed citation Europe PMC
15180134 PubMed citation Europe PMC
16845152 PubMed citation Europe PMC
18071034 PubMed citation Europe PMC
2012117 PubMed citation Europe PMC
Last Modified
22 February 2017