3594. Entacapone

Nomenclature

CAS number: 130929-57-6
(2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide; (E)-α-cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide; (E)-2-cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide; OR-611; Comtan (Orion); Comtess (Orion).
C14H15N3O5; mol wt 305.29.
C 55.08%, H 4.95%, N 13.76%, O 26.20%.

Description and references

Peripherally acting inhibitor of catechol-O-methyl transferase (COMT), an enzyme involved in the metabolism of catecholamine neurotransmitters and related drugs. Prepn (stereochemistry unspecified): R. J. B"ackstr"om et al., DE 3740383; eidem, US 5446194 (1988, 1995 both to Orion). Prepn of (E)-isomer: A. K. Pippuri et al., EP 426468; eidem, US 5135950 (1991, 1992 both to Orion). Pharmacology: E. Nissinen et al., Arch. Pharmacol. 346, 262 (1992). LC determn in plasma and urine: M. Karlsson, T. Wikberg, J. Pharm. Biomed. Anal. 10, 593 (1992). Identification of metabolites: T. Wikberg et al., Eur. J. Drug Metab. Pharmacokinet. 18, 359 (1993). Clinical pharmacokinetics: T. Ker"anen et al., Eur. J. Clin. Pharmacol. 46, 151 (1994). Clinical effect on levodopa bioavailability in Parkinson's disease: H. M. Routtinen, U. K. Rinne, J. Neurol. Neurosurg. Psychiatry 60, 36 (1996).

Chemical structure

Properties

Crystals from acetic acid + HCl, mp 162-163°. pKa ≈4.5.

Therapeutic Category

Antiparkinsonian.

Keywords

Antiparkinsonian; COMT Inhibitor