Entacapone

Entacapone
Systematic (IUPAC) name
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Clinical data
Trade names Comtan
AHFS/Drugs.com monograph
MedlinePlus a601236
Pregnancy cat. C(US)
Legal status Prescription only, unscheduled (USA)
Routes Oral
Pharmacokinetic data
Bioavailability 35%
Protein binding 98% (binds to serum albumin)
Metabolism Hepatic
Half-life 0.4-0.7 hour
Excretion 90% feces, 10% urine
Identifiers
CAS number 130929-57-6
ATC code N04BX02
PubChem CID 5281081
DrugBank APRD00416
ChemSpider 4444537 Y
UNII 4975G9NM6T Y
KEGG D00781 Y
ChEBI CHEBI:4798 Y
ChEMBL CHEMBL953 Y
Synonyms
Chemical data
Formula C14H15N3O5 
Mol. mass 305.286 g/mol
SMILES eMolecules & PubChem
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Entacapone (INN) ( /ˌɛntəkəˈpn/ or /ɛnˈtækəpn/) 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.

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 diarrhoea, nausea and abdominal pains. The substance 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 Novartis medication that contains entacapone in combination with carbidopa and levodopa (active ingredients in Sinemet).

References

External links