Entacapone

Originator

Comtan,Orion Corporation

Definition

ChEBI: Entacapone is 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. It has a role as an EC 2.1.1.6 (catechol O-methyltransferase) inhibitor, an antiparkinson drug, a central nervous system drug and an antidyskinesia agent. It is a monocarboxylic acid amide, a nitrile, a member of catechols and a member of 2-nitrophenols.

Manufacturing Process

N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide (2- Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl).
A solution containing 1.83 g of 3,4-dihydroxy-5-nitrobenzaldehyde, 1.5 g of N,N-diethylcyanoacetamide and catalytic amount of piperidine acetate in 40 ml of dry ethanol was refluxed over night. After cooling the solvent was evaporated in vacuo and the residue was recrystallized from waterdimethylformamide. Yield of desired product was 2.23 g (73%), melting point 153°-156°C.

Therapeutic Function

Antiparkinsonian