(E )-2- cyano-3- (3,4- dihydroxy -5-nitro -phenyl)- N, N- diethyl- prop-2- enamide


COMT inhibitors

162-163 ° C

Template: Infobox chemical / molecular formula search available

Entacapone is a drug for the treatment of Parkinson's disease. The active substance belongs to the class of catechol -O-methyltransferase inhibitors, known as COMT inhibitors.

Field of application

The drug is for the treatment of Parkinson's disease that develop motor fluctuations from L- DOPA therapy, are used. It prevents the breakdown of dopamine and the precursor L-DOPA by the COMT ( catechol-O- methyltransferase ) to inactive metabolites and is taken with each levodopa dose. The efficacy of the drug in the treatment of fluctuations is confirmed by studies. A prevention or delay the occurrence of fluctuations effect by the treatment of patients with stable levodopa response with COMT inhibitors has so far been established only in animal experiments. In this respect human studies are currently being carried out according to the German Society of Neurology.

Contraindications include liver failure and pheochromocytoma. Coadministration of entacapone with non-selective monoamine oxidase inhibitors (MAO -A and MAO -B, such as phenelzine, tranylcypromine ) is contraindicated. Co-administration of a selective MAO -A inhibitor and a selective MAO - B inhibitor and entacapone is also contraindicated

  • Administration: oral
  • Plasma half-life: 0.4-0.7 hours
  • Elimination: 90% faecal, 10 % renal

Production and representation

The preparation of entacapone is effected by a Knoevenagel Kondenstion of 3,4- dihydroxy- 5-nitrobenzaldehyde with 2-cyano- N, N- diethylacetamide. In this synthesis variant, the (E ) are produced - and (Z )-isomer in the ratio 2:1. Separation of the isomers can be effected by a crystallization of the hydrochloride salts.

Trade names

Comtan (A, CH), Comtess (D, A)

Stalevo (D, A, CH) (in combination with L- dopa and carbidopa )