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Entacapone (INN) (/ˌɛntəkəˈpoʊn/ or /ɛnˈtækəpoʊn/) is a drug that functions as a catechol-O-methyl transferase (COMT) inhibitor. It is used in the treatment of Parkinson's disease.

When administered in conjunction with dopaminergic agents such as L-DOPA, entacapone prevents COMT from metabolizing L-DOPA into 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD) in the periphery, which does not easily cross the blood–brain barrier (BBB). Pharmacologically, entacapone is somewhat similar to carbidopa or benserazide, in that it is an inhibitor of an enzyme that converts L-DOPA into a compound that cannot cross the blood–brain barrier. Carbidopa and benserazide inhibit aromatic L-amino acid decarboxylase, which converts L-DOPA into dopamine, which cannot cross the blood–brain barrier.

Entacapone is a member of the class of drugs known as nitrocatechols.

Side effects

The most frequent undesirable effects caused by entacapone relate to the increased effects of L-DOPA, such as involuntary movements (dyskinesias). These occur most frequently at the beginning of entacapone treatment. Others common side effects are gastrointestinal problems, including nausea and abdominal pains. Diarrhea is a frequently reported and troublesome side effect that can result in unnecessary investigation, but resolves quickly on withdrawal of the drug. Entacapone may cause urine to turn reddish-brown. This is a harmless side effect and is not a cause for concern. In studies with entacapone, some people have reported experiencing a dry mouth.

Products

Entacapone is developed by Orion Pharma and marketed by Novartis under the trade name COMTan in the United States.

Stalevo is another medication developed by Orion Pharma and marketed by Novartis that contains entacapone in combination with carbidopa and levodopa (active ingredients in Sinemet).

External links

• Entacapone/Carbidopa/Levodopa (marketed as Stalevo) Information (FDA)
• Entacapone (Medline plus/NIH)
• Comtan (manufacturer's website)
• Stalevo (manufacturer's website)

Entacapone

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Systematic (IUPAC) name
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Clinical data
Trade names	Comtan (single ingredient), Stalevo (multi-ingredient)
AHFS/Drugs.com	monograph
MedlinePlus	a601236
Licence data	US Daily Med:link
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Legal status	AU: Prescription Only (S4) CA: ℞-only UK: Prescription-only (POM) US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	35%
Protein binding	98% (binds to serum albumin)
Metabolism	Hepatic
Half-life	0.4-0.7 hour
Excretion	Faeces (90%), Urine (10%)
Identifiers
CAS Registry Number	130929-57-6 7pxY
ATC code	N04BX02
PubChem	CID 5281081
DrugBank	DB00494 7pxY
ChemSpider	4444537 7pxY
UNII	4975G9NM6T 7pxY
KEGG	D00781 7pxY
ChEBI	CHEBI:4798 7pxY
ChEMBL	CHEMBL953 7pxY
Synonyms	</td></tr>
Chemical data
Formula	C14H15N3O5</td></tr>
Molecular mass	305.286 g/mol</td></tr>
SMILES [O-][N+](=O)c1cc(\C=C(/C#N)C(=O)N(CC)CC)cc(O)c1O </td></tr>
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+  7pxY Key:JRURYQJSLYLRLN-BJMVGYQFSA-N  7pxY </td></tr></th></tr>
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