CHEBI:4798 - entacapone

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ChEBI Name entacapone
ChEBI ID CHEBI:4798
Definition A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H15N3O5
Net Charge 0
Average Mass 305.28612
Monoisotopic Mass 305.101
InChI InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
InChIKey JRURYQJSLYLRLN-BJMVGYQFSA-N
SMILES CCN(CC)C(=O)C(\C#N)=C\c1cc(O)c(O)c(c1)[N+]([O-])=O
Roles Classification
Biological Role(s): EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).
Application(s): central nervous system drug
A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.
antidyskinesia agent
Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
antiparkinson drug
A drug used in the treatment of Parkinson's disease.
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ChEBI Ontology
Outgoing entacapone (CHEBI:4798) has role antidyskinesia agent (CHEBI:66956)
entacapone (CHEBI:4798) has role antiparkinson drug (CHEBI:48407)
entacapone (CHEBI:4798) has role central nervous system drug (CHEBI:35470)
entacapone (CHEBI:4798) has role EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (CHEBI:48406)
entacapone (CHEBI:4798) is a 2-nitrophenols (CHEBI:86421)
entacapone (CHEBI:4798) is a catechols (CHEBI:33566)
entacapone (CHEBI:4798) is a monocarboxylic acid amide (CHEBI:29347)
entacapone (CHEBI:4798) is a nitrile (CHEBI:18379)
Incoming 3-O-ethylentacapone (CHEBI:48380) has functional parent entacapone (CHEBI:4798)
3-O-methylentacapone (CHEBI:48381) has functional parent entacapone (CHEBI:4798)
IUPAC Name
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
INNs Sources
entacapona ChemIDplus
entacapone KEGG DRUG
entacaponum ChemIDplus
Synonyms Sources
(E)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide ChemIDplus
Comtess DrugBank
Entacapone KEGG COMPOUND
N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide Patent
Brand Name Source
Comtan DrugBank
Database Links Databases
1018 DrugCentral
C07943 KEGG COMPOUND
D00781 KEGG DRUG
DB00494 DrugBank
Entacapone Wikipedia
EP426468 Patent
US5135950 Patent
US6599530 Patent
WO2005063693 Patent
View more database links
Registry Numbers Types Sources
130929-57-6 CAS Registry Number KEGG COMPOUND
130929-57-6 CAS Registry Number ChemIDplus
8158723 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11244274 PubMed citation Europe PMC
11586115 PubMed citation Europe PMC
11732751 PubMed citation Europe PMC
12952501 PubMed citation Europe PMC
15698633 PubMed citation Europe PMC
15875340 PubMed citation Europe PMC
15878587 PubMed citation Europe PMC
15992091 PubMed citation Europe PMC
19578428 PubMed citation Europe PMC
19879254 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-07-19 Entacapone is a selective and reversible inhibitor of catechol O-methyltransferase, an enzyme involved in dopamine and levodopa metabolism, and thus slows the metabolism of levodopa, so prolonging its effects. It is used as an adjunct to combination preparations of levodopa and dopa-decarboxylase inhibitors in patients with Parkinson's disease and 'end of dose' motor fluctuations who cannot be stabilised using levodopa combinations alone.