311. Alpiropride

Nomenclature

CAS number: 81982-32-3
4-Amino-2-methoxy-5-[(methylamino)sulfonyl]-N-[[1-(2-propen-1-yl)-2-pyrrolidinyl]methyl]benzamide; (±)-N-[(1-allyl-2-pyrrolidinyl)methyl]-4-amino-5-(methylsulfamoyl)-o-anisamide; N-(1-allyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-methylsulfamoylbenzamide; RIV-2093; Rivistel (Delagrange).
C17H26N4O4S; mol wt 382.48.
C 53.38%, H 6.85%, N 14.65%, O 16.73%, S 8.38%.

Description and references

Dopamine D2-receptor antagonist structurally similar to sulpiride, q.v. Prepn: J. Perrot, M. Thominet, EP 47207; eidem, US 4550179 (1982, 1985 both to Soc. d'Etudes Sci. Ind. l'Ile-de-France). Dopamine receptor binding study: P. Sokoloff et al., Arch. Pharmacol. 327, 221 (1984). HPLC determn in plasma and urine: F. Bressolle et al., J. Chromatogr. 343, 443 (1985). Pharmacokinetics and metabolism in humans: F. Bressolle et al., J. Pharm. Clin. 4, 261 (1985). Preliminary study in experimentally induced migraine: A. Bès et al., Int. J. Clin. Pharmacol. Res. 6, 189 (1986).

Chemical structure

Properties

Crystals from absolute ethanol, mp 168.5-169°. LD50 in male mice (mg/kg): 44 i.v.; 184 i.p.; 204 s.c.; 3600 orally (Perrot, Thominet, 1985).

Therapeutic Category

Antimigraine.

Keywords

Antimigraine