Structure via PubChem · Public domain (PubChem)
entacapone
Sign in to saveAlso known as COM998, OR-611, (E)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide, N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide
Entacapone, sold under the brand name Comtan among others, is a medication commonly used in combination with other medications for the treatment of Parkinson's disease. Entacapone together with levodopa and carbidopa allows levodopa to have a longer effect in the brain and reduces Parkinson's disease signs and symptoms for a greater length of time than levodopa and carbidopa therapy alone.
Chemical data
- Formula
- C14H15N3O5
- Molecular weight
- 305.29 g/mol
- IUPAC name
- (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
- SMILES
- CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N
- InChIKey
- JRURYQJSLYLRLN-BJMVGYQFSA-N
- XLogP
- 2.1
- Polar surface area
- 130 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
865 papers- Entacapone.The Annals of pharmacotherapy · 2000
- Entacapone.Expert opinion on drug metabolism & toxicology · 2010
- Levodopa/carbidopa/entacapone for the treatment of early Parkinson's disease: a meta-analysis.Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology · 2020
- Catechol-O-methyltransferase inhibition with entacapone: Evidence from controlled clinical trials in Parkinson's disease.European journal of neurology · 2023
- Entacapone/levodopa/carbidopa combination tablet: Stalevo.Drugs in R&D · 2003
via PubMed
Wikidata facts
- Mass
- 305.101171
Show 6 more facts
- chemical formula
- C₁₄H₁₅N₃O₅
- Commons category
- Entacapone
- defined daily dose
- 1
- canonical SMILES
- CCN(CC)C(=O)C(=CC1=CC(=C(C(=C1)O)O)[N+](=O)[O-])C#N
- isomeric SMILES
- CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N
- World Health Organisation international non-proprietary name
- entacapone
Sources (9)
via Wikidata · CC0
~8 min read
Article
23 sectionsContents
- Medical uses
- Pregnancy and breastfeeding
- Children
- Liver problems
- Kidney problems
- Contraindications
- Side effects
- Movement problems
- Diarrhea
- Urine color
- Sudden sleep onset
- Low blood pressure
- Behavior problems
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism and elimination
- Research
- Restless legs syndrome
- References
Entacapone, sold under the brand name Comtan among others, is a medication commonly used in combination with other medications for the treatment of Parkinson's disease. Entacapone together with levodopa and carbidopa allows levodopa to have a longer effect in the brain and reduces Parkinson's disease signs and symptoms for a greater length of time than levodopa and carbidopa therapy alone.
Entacapone is a selective and reversible inhibitor of the enzyme catechol-O-methyltransferase (COMT). When taken together with levodopa (L-DOPA) and carbidopa, entacapone stops COMT from breaking down levodopa, resulting in an overall increase of levodopa remaining in the brain and body. Entacapone does not cross into the brain and hence does not inhibit COMT there.