Entacapone

Entacapone

Clinical data
Pronunciation	/ˌɛntəkəˈpoʊn/ or /ɛnˈtækəpoʊn/
Trade names	Comtan (single ingredient), Stalevo (multi-ingredient)
AHFS/Drugs.com	Monograph
MedlinePlus	a601236
License data	US DailyMed: e41bbc90-bb83-4514-a38f-994e9fa76472
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	N04BX02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	35%
Protein binding	98% (binds to serum albumin)
Metabolism	Hepatic
Biological half-life	0.4–0.7 hours
Excretion	Feces (90%), urine (10%)
Identifiers
IUPAC name (2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
CAS Number	130929-57-6 Y
PubChem CID	5281081
IUPHAR/BPS	6647
DrugBank	DB00494 Y
ChemSpider	4444537 Y
UNII	4975G9NM6T
KEGG	D00781 Y
ChEBI	CHEBI:4798 Y
ChEMBL	CHEMBL953 Y
ECHA InfoCard	100.128.566
Chemical and physical data
Formula	C14H15N3O5
Molar mass	305.286 g/mol
3D model (Jmol)	Interactive image
SMILES [O-][N+](=O)c1cc(\C=C(/C#N)C(=O)N(CC)CC)cc(O)c1O
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+ Y Key:JRURYQJSLYLRLN-BJMVGYQFSA-N Y

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 known as a selective and reversible inhibitor of the enzyme catechol-O-methyltransferase (COMT). When taken together with levodopa (L-DOPA) and carbidopa, entacapone stops catechol-O-methyltransferase from breaking down and metabolizing levodopa, resulting in an overall increase of levodopa remaining in the brain and body.

Carbidopa/levodopa/entacapone (Stalevo), another medication developed by Orion Pharma and marketed by Novartis, is a single tablet formulation that contains levodopa, carbidopa, and entacapone.

Entacapone is used in addition to levodopa and carbidopa for people with Parkinson's disease to treat the signs and symptoms of end-of-dose "wearing-off." "Wearing-off" is characterized by the re-appearance of both motor and non-motor symptoms of Parkinson’s disease occurring towards the end of a previous levodopa and carbidopa dose. In clinical trials, entacapone has not been shown to slow progression or reverse Parkinson’s disease.

Entacapone is an orally active drug that can be taken with or without food.

Pregnancy category C: risk is not ruled out.