Tiotropium bromide monohydrate

• CAT Number: I020701
• CAS Number: 411207-31-3
• Molecular Formula: C19H24BrNO5S2
• Molecular Weight: 490.43
• Purity: ≥95%
• Synonyms: [(1R,2R,4S,5S)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;bromide;hydrate
• InChI: InChI=1S/C19H22NO4S2.BrH.H2O/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15;;/h3-8,11-13,16-17,22H,9-10H2,1-2H3;1H;1H2/q+1;;/p-1/t11?,12-,13+,16-,17+
• InChIKey: MQLXPRBEAHBZTK-KFEMZTBUSA-M
• SMILES: C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.O.[Br-]

Tiotropium bromide monohydrate is an anticholinergic and bronchodilator and a muscarinic receptor antagonist.
Target: mAChR
Tiotropium bromide (Ba 679 BR) is a novel potent and long-lasting muscarinic antagonist that has been developed for the treatment of chronic obstructive airways disease (COPD). Binding studies with [3H]tiotropium bromide in human lung have confirmed that this is a potent muscarinic antagonist with equal affinity for M1-, M2- and M3-receptors and is approximately 10-fold more potent than ipratropium bromide. In vitro tiotropium bromide has a potent inhibitory effect against cholinergic nerve-induced contraction of guinea-pig and human airways, that has a slower onset than atropine or ipratropium bromide. tiotropium bromide dissociates slowly from M3-receptors (on airway smooth muscle) but rapidly from M2 autoreceptors (on cholinergic nerve terminals) [1]. Tiotropium bromide is a quaternary ammonium derivative that binds to muscarinic receptors. However, although tiotropium binds with high affinity to muscarinic receptors of M1-, M2- and M3-subtypes, it dissociates very slowly from M1- and M3-receptors but more rapidly from M2-receptors, thereby giving it a unique kinetic selectivity [2].

Reference

[1]. Barnes, P.J., et al., Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci, 1995. 56(11-12): p. 853-9.
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[2]. Hansel, T.T. and P.J. Barnes, Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc), 2002. 38(9): p. 585-600.
 [Content Brief]