9508. Tolcapone

Nomenclature

CAS number: 134308-13-7
(3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone; 3,4-dihydroxy-4′-methyl-5-nitrobenzophenone; Ro-40-7592; Tasmar (Valeant).
C14H11NO5; mol wt 273.24.
C 61.54%, H 4.06%, N 5.13%, O 29.28%.

Description and references

Orally active inhibitor of central and peripheral catechol-O-methyltransferase (COMT). Prepn: K. Bernauer et al., EP 237929; eidem, US 5236952 (1987, 1993 both to Hoffmann-La Roche). Pharmacology: G. Zürcher et al., Adv. Neurol. 53, 497 (1990). HPLC determn in plasma: U. Timm, R. Erdin, J. Chromatogr. 593, 63 (1992). Clinical pharmacokinetics: J. Dingemanse et al., Clin. Pharmacol. Ther. 57, 508 (1995). Clinical evaluation as adjunct to levodopa: P. Limousin et al., Clin. Neuropharmacol. 18, 258 (1995). Review of pharmacology and clinical experience: G. M. Keating, K. A. Lyseng-Williamson, CNS Drugs 19, 165-184 (2005); of safety and efficacy: N. Borges, Expert Opin. Drug Saf. 4, 69-73 (2005).

Chemical structure

Properties

Crystals from methylene chloride, mp 146-148°.

Therapeutic Category

Antiparkinsonian.

Keywords

Antiparkinsonian; COMT Inhibitor