9786. Trospium Chloride

Nomenclature

CAS number: 10405-02-4
(1α,3β,5α)-3-[(Hydroxydiphenylacetyl)oxy]spiro[8-azoniabicyclo[3.2.1]octane-8,1′-pyrrolidinium] chloride; 3α-hydroxyspiro[1αH,5αH-nortropane-8,1′-pyrrolidinium] chloride benzilate; azoniaspiro(3α-benziloyloxynortropane-8,1′-pyrrolidine) chloride; azoniaspiro(3α-diphenylglycoloyloxynortropan-8,1′-pyrrolidine) chloride; 3α-benziloyloxyspiro(nortropane-8,1′-pyrrolidinium) chloride; Regurin (Galen); Relaspium (Isei); Sanctura (Indevus); Spasmex (Pfleger); Spasmolyt (Madaus).
C25H30ClNO3; mol wt 427.96.
C 70.16%, H 7.07%, Cl 8.28%, N 3.27%, O 11.22%.

Description and references

Tropine derivative with anticholinergic activity. Prepn: NL 6402155; R. Pfleger et al., US 3480626 (1964, 1969 both to Pfleger); H. Bertholdt et al., Arzneim.-Forsch. 17, 719 (1967). Pharmacology and toxicology in animals: H. Antweiler et al., ibid. 16, 1581 (1966). Inhibition of gastric motility and acid secretion in humans: G. Lux, P. Frühmorgen, Fortschr. Med. 96, 2113 (1978). Fluorimetric determn in plasma and urine: G. Schladitz-Keil et al., J. Chromatogr. 345, 99 (1985). Bioavailability: eidem, Arzneim.-Forsch. 36, 984 (1986). Clinical trial in bladder hyper-reflexia: H. Madersbacher et al., Br. J. Urol. 75, 452 (1995). Review in overactive bladder: N. R. Zinner, Expert Opin. Pharmacother. 6, 1409-1420 (2005).

Chemical structure

Properties

Crystals from ethanol-ether, mp 255-257° (dec). Soly in water: ≈1 g/2 ml. LD50 in mice (mg/kg): 12.3 i.v. (Antweiler).

Therapeutic Category

Antispasmodic; in treatment of urinary incontinence.

Keywords

Antimuscarinic; Antispasmodic