Tiotropium Bromide Basic Information
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Product Name |
Tiotropium Bromide |
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Synonyms |
(1α,2β,4β,5α,7β)-7-[(Hy-droxydi-2-thienylacetyl)axy]-9,9-dimethyl-3-oxa-9-azoniatri-cyclo[3.3.1.02.4]nonane;(1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide;Anhydrous Tiotropium Bromide;3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane, 7-[(2-hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-, bromide (1:1), (1α,2β,4β,5α,7β)-;(1R,2R,4S,5S,7s)-7-[(2-Hydroxy-2,2-dithiophen-2-ylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide monohydrate;(1a,2,4,5a,7)-7-[(2-Hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane Bromide;(1α,2β,4β,5α,7β-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3．3．1．0^<2,4>^]nonane bromide;Ba-679 |
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CAS |
136310-93-5 |
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MF |
C19H22BrNO4S2 |
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MW |
472.42 |
| EINECS | 680-665-7 |
Tiotropium Bromide Properties
| Melting point | 218-2200C |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| color | White to Off-White |
| λmax | 240nm(lit.) |
| Merck | 14,9454 |
Tiotropium Bromide Usage
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Uses |
Atropine derivatives. Bronchodilator drugs. Muscarinic receptor antagonist |
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Description |
Tiotropium bromide is a long-acting inhaled muscarinic antagonist, developed for the once-daily treatment of chronic obstructive pulmonary disease. Tiotropium bromide can be prepared in three steps. The Grignard condensation of 2-thienyl magnesium bromide with oxalic acid dimethyl ester, followed by a transesterlfication with scopine provided the ester which was quaternized with methyl bromide. Tiotropium bromide binds to human recombinant muscarinic receptors M1-, M2- and M3-subtypes with high and similar affinity, comparable to those obtained with ipratropium. Tiotropium bromide is characterized by its novel property of kinetic selectivity : while ipratropium rapidly dissociated from each of the receptor subtypes, tiotropium dissociated rapidly from M2 receptors (t1/2=3.6 h) but slowly from MI (t1/2=14.6 h) and M3 (t1/2=34.7 h) receptors. Inhibition of cholinergic bronchospasm by tiotropium bromide was demonstrated in anesthetized guinea pigs, rabbits and dogs. In healthy volunteers, inhalation of tiotropium bromide resulted in an absolute bioavailability of 19.5%, a t,,, value of 5 min. and the terminal half-life value of 5-6 days. There was no evidence of drug accumulation after repeated administration. The extent of biotransfonation was small with a urinary excretion of 74% of unchanged substance after iv. administration. Long term studies in patients with stable COPD have demonstrated that tiotropium bromide gave an effective bronchodilation that was maintained over 24h, significantly improved lung function as measured by FEVI (+ll-12%) and showed progressive reduction in dyspnea. It also reduced exacerbations of COPD patients and improved quality of life. Tiotropium bromide produced greater and more sustained bronchodilation than ipratropium bromide. Tiotropium has been shown to cause superior bronchodilatation and symptomatic improvements when compared to twice daily salmeterol in COPD. Tiotropium bromide was well tolerated and caused few adverse effects. The most common side effect reported was the mechanism-related effect of dry mouth. |
Pharmacological action
This product is a quaternary ammonium derivative. It is a long-acting anticholinergic drug. It has the same affinity for 5 muscarinic receptors of M1～M5 type. By binding to muscarinic receptors on bronchial smooth muscles, it inhibits the release of parasympathetic nerve terminals. Contraction of the trachea caused by acetylcholine. In the human airway, this product has a high affinity with receptors, and dissociates slowly from muscarinic M1 and M3 receptors. It can block cholinergic nerve-mediated bronchial smooth muscle contraction for a long time, and can expand the bronchus for a long time. , Effectively improve lung function, relieve breathing difficulties, reduce the frequency of chronic obstructive pulmonary disease (COPD) aggravation, curb the deterioration of the disease, and improve the quality of life. This product improves the selectivity of M1 and M3 receptors and prolongs the action time, thereby avoiding side effects such as saliva secretion and dilated pupils caused by M2 receptor blockade.
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