1534. Butropium Bromide

Nomenclature

CAS number: 29025-14-7
[3(S)-endo]-8-[(4-Butoxyphenyl)methyl]-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-azoniabicyclo[3.2.1]octane bromide; 8-(p-butoxybenzyl)-3α-hydroxy-1αH,5αH-tropanium bromide (-)-tropate; l-[1-(p-n-butoxybenzyl)hyoscyaminium] bromide; BHB; Coliopan (Eisai).
C28H38BrNO4; mol wt 532.51.
C 63.15%, H 7.19%, Br 15.01%, N 2.63%, O 12.02%.

Description and references

Anticholinergic. Prepn: S. Tanaka, K. Hashimoto, DE 1950378; eidem, US 3696110 (1970, 1972 both to Eisai); Tanaka et al., J. Pharm. Soc. Jpn. 92, 510 (1972). Prepn of the labelled compound: Fujita et al., J. Labelled Compd. 9, 149, 555 (1972). Activity: Akutsu, Ichikawa, Showa Igakkai Zasshi 32, 494 (1972), C.A. 78, 119243g (1973).

Chemical structure

Properties

Crystals from ethanol-acetone, mp 166-168°; also reported as white needles from isopropanol, mp 158-160° (Tanaka, Hashimoto). [α]D20 -21.7° (c = 0.5 in water). Freely sol in glacial acetic acid; sol in chloroform, DMF. Sparingly sol in ethanol; slightly sol in water, 0.1N HCl, 0.1N NaOH. Practically insol in acetone, ether, benzene. LD50 in male mice (mg/kg): 1500 orally; 660 s.c.; 12.0 i.v. (Tanaka, Hashimoto, 1972).

Therapeutic Category

Antispasmodic.

Keywords

Antispasmodic; Antimuscarinic