8315. Safinamide

Nomenclature

CAS number: 133865-89-1
(2S)-2-[[[4-[(3-Fluorophenyl)methoxy]phenyl]methyl]amino]propanamide; (S)-(+)-2-[[4-(3-fluorobenzoxy)benzyl]amino]propanamide; FCE-26743.
C17H19FN2O2; mol wt 302.34.
C 67.53%, H 6.33%, F 6.28%, N 9.27%, O 10.58%.

Description and references

Voltage-dependent sodium and calcium channel blocker; selective and reversible inhibitor of monoamine oxidase B (MAO-B). Prepn: P. Dostert et al., EP 400495; eidem, US 5236957 (1990, 1993 both to Farmitalia); and anticonvulsant activity: P. Pevarello et al., J. Med. Chem. 41, 579 (1998) DOI PubMed. Mechanism of action study: P. Salvati et al., J. Pharmacol. Exp. Ther. 288, 1151 (1999) PubMed. Review of early clinical development: P. L. Chazot, Curr. Opin. Investig. Drugs 2, 809-813 (2001) PubMed. Clinical pharmacokinetics and pharmacodynamics: A. Marzo et al., Pharmacol. Res. 50, 77 (2004) DOI PubMed. Clinical evaluation in Parkinson's disease: F. Stocchi et al., Neurology 63, 746 (2004) PubMed.

Chemical structure

Properties

mp 208-212°.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 202825-46-5
Safinamide mesylate; NW-1015; PNU-151774E.
C17H19FN2O2.CH4O3S; mol wt 398.45.
C 54.26%, H 5.82%, F 4.77%, N 7.03%, O 20.08%, S 8.05%.

Properties

mp 210° (dec). [α]D25 +12.9° (c = 1.1% in 98% acetic acid).

Therapeutic Category

Antiparkinsonian; anticonvulsant.

Keywords

Monoamine Oxidase Inhibitor; Anticonvulsant; Antiparkinsonian