9454. Tiotropium Bromide

Nomenclature

CAS number: 136310-93-5
(1α,2β,4β,5α,7β)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide; 6β,7β-epoxy-3β-hydroxy-8-methyl-1αH,5αH-tropanium bromide, di-2-thienylglycolate; Ba-679 BR; Ba-679; Spiriva (Boehringer, Ing.).
C19H22BrNO4S2; mol wt 472.42.
C 48.31%, H 4.69%, Br 16.91%, N 2.96%, O 13.55%, S 13.57%.

Description and references

Muscarinic receptor antagonist. Prepn: R. Banholzer et al., EP 418716; eidem, US 5610163 (1991, 1997 both to Boehringer Ingelheim). Pharmacology: T. Takahashi et al., Am. J. Respir. Crit. Care Med. 150, 1640 (1994). Binding study: E.-B. Haddad et al., Mol. Pharmacol. 45, 899 (1994). Comparative clinical trial with salmeterol, q.v., in chronic obstructive pulmonary disease (COPD): J. F. Donohue et al., Chest 122, 47 (2002).

Chemical structure

Properties

mp 218-220°.

Therapeutic Category

Bronchodilator.

Keywords

Bronchodilator; Quaternary Ammonium Compounds; Antimuscarinic