Fentonium Bromide

Title: Fentonium Bromide
CAS Registry Number: 5868-06-4
CAS Name: [3(S)-endo]-8-(2-[1,1¢-Biphenyl]-4-yl-2-oxoethyl)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-azoniabicyclo[3.2.1]octane bromide
Additional Names: 3a-hydroxy-8-(p-phenylphenacyl)-1aH,5aH-tropanium bromide (-)-tropate; N-(4-phenylphenacyl)-1-hyoscyaminium bromide; phentonium bromide
Manufacturers' Codes: FA-402; Z-326
Trademarks: Ketoscilium (Zambon); Ulcesium (Zambon)
Molecular Formula: C31H34BrNO4
Molecular Weight: 564.51
Percent Composition: C 65.96%, H 6.07%, Br 14.15%, N 2.48%, O 11.34%
Literature References: Anticholinergic. Prepn: U. Teotino, D. Della Bella, GB 1026640; eidem, US 3356682 (1966, 1967 both to Whitefin Holding); Teotino et al., Chim. Ther. 3, 453 (1968). Human pharmacology: Azzollini et al., Curr. Ther. Res. 12, 734 (1970). Clinical studies: Alberto et al., Minerva Med. 62, 852 (1971).
Properties: Crystals, mp 203-205° (dec). [a]D23 -5.68° (c = 5 in DMF). Also reported as mp 193-194°. [a]D25 -4.7° (c = 5 in DMF). LD50 in mice (mg/kg): 12.1 i.v.; >400 s.c. and orally (Teotino, Della Bella).
Melting point: mp 203-205° (dec); mp 193-194°
Optical Rotation: [a]D23 -5.68° (c = 5 in DMF); [a]D25 -4.7° (c = 5 in DMF)
Toxicity data: LD50 in mice (mg/kg): 12.1 i.v.; >400 s.c. and orally (Teotino, Della Bella)
Therap-Cat: Antispasmodic.
Keywords: Antispasmodic; Antimuscarinic.
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