4501. Glycopyrrolate
Nomenclature
CAS number: 596-51-0
3-[(Cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium
bromide; 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate; α-cyclopentylmandelic acid ester with 3-hydroxy-1,1-dimethylpyrrolidinium
bromide; 1-methyl-3-pyrrolidyl α-cyclopentylmandelate methobromide; 1-methyl-3-pyrrolidyl α-phenyl-α-cyclopentylglycolate methobromide; 3-(2-phenyl-2-cyclopentylglycoloyloxy)-1,1-dimethylpyrrolidinium
bromide; glycopyrronium bromide; AHR-504; Nodapton; Robanul; Robinul (Robins); Tarodyl; Tarodyn. C19H28BrNO3; mol wt 398.33.
C 57.29%, H 7.09%, Br 20.06%, N 3.52%, O 12.05%.
Description and references
Synthetic, quaternary ammonium anticholinergic. Prepn: Franko, Lunsford, J. Med. Pharm. Chem. 2, 523 (1960); Lunsford, US 2956062 (1960 to A. H. Robins). Pharmacodynamics: E. Kaltiala et al., J. Pharm. Pharmacol. 26, 352 (1974). Toxicology: B. V. Franko et al., Toxicol. Appl. Pharmacol. 17, 361 (1970). Clinical comparison with atropine in anaesthetic practice: F. Kongsrud, S. Sponheim, Acta Anaesthesiol. Scand. 26, 620 (1982); A. I. Webb, R. M. McMurphy, Am. J. Vet. Res. 48, 1733 (1987); B. V. G. Malling et al., Br. J. Anaesth. 60, 426 (1988). Brief review of pharmacology and clinical use: R. K. Mirakhur, J. W. Dundee, Anaesthesia 38, 1195-1204 (1983).
Properties
White crystals from butanone, mp 193.2-194.5°. Sol in water. LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.; in male rats (mg/kg): 1150 orally (Franko).Therapeutic Category
Antispasmodic; preanesthetic medicant.
Therapeutic Category (Veterinary)
Preanesthetic medicant.Keywords
Antimuscarinic; Antispasmodic