136310-93-5

Basic information

• Product Name: Tiotropium bromide
• 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;(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^^]nonane bromide;Ba-679;Ba-679 BR;otropiuM broMide;TiotropiuM broMide anhydrous
• CAS NO: 136310-93-5
• Molecular Formula: C19H22BrNO4S2
• Molecular Weight: 472.42
• EINECS: 1308068-626-2
• Product Categories: API;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Tiotropium;stock for supply, stable production, we can also offer commerical quantity
• Mol File: 136310-93-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 218-2200C
• Appearance: White solid
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Merck: 14,9454
• CAS DataBase Reference: Tiotropium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Tiotropium bromide(136310-93-5)
• EPA Substance Registry System: Tiotropium bromide(136310-93-5)

Safety Data

• Hazardous Substances Data: 136310-93-5(Hazardous Substances Data)

Usage

Description

Tiotropium bromide, also known as Spiriva, is a long-acting inhaled muscarinic antagonist used for the maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD). It is a white solid that binds to M1, M2, and M3 muscarinic acetylcholine receptors, decreasing acetylcholine-induced contraction of the trachea and providing bronchodilation.

Uses

1. Used in Pharmaceutical Industry:
Tiotropium bromide is used as a muscarinic receptor antagonist for the treatment of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. It provides effective bronchodilation that is maintained over 24 hours, significantly improves lung function as measured by FEV1 (+11-12%), and shows a progressive reduction in dyspnea.
2. Used in Respiratory Medicine:
Tiotropium bromide is used as a bronchodilator for patients with COPD. It offers superior bronchodilatation and symptomatic improvements when compared to twice daily salmeterol in COPD patients.
3. Used in Drug Resistance:
Tiotropium bromide is used as a selectively selective choline drug to combat resistance in the treatment of COPD.
4. Used in Asthma Treatment:
Tiotropium bromide is used as an anti-asthmatic agent to help manage and alleviate asthma symptoms.
5. Used in Long-term COPD Management:
Tiotropium bromide is used in long-term studies to reduce exacerbations of COPD patients and improve their quality of life. It has been shown to produce greater and more sustained bronchodilation than ipratropium bromide.
Note: The provided materials do not mention the use of Glycerol, so the usage of Glycerol cannot be listed based on the given information.

Originator

Boehringer lngelheim (Germany)

Pharmacokinetics

Tiotropium is administered as a dry powder via inhalation using a HandiHaler, in which is placed the drug, contained in a green capsule. Patients should be cautioned not to be confused and take the medication orally. Systemic distribution following oral inhalation is minimal, essentially because of its hydrophilic character. If swallowed, only approximately 14% of the dose is eliminated in the urine, with the remainder being found in the feces. Inhaled tiotropium has a 30-minute onset of action but a much longer duration of action than ipratropium (24 versus <4 hours, respectively). Tiotropium is metabolized by both CYP3A4 and CYP2D6, followed by glutathione conjugation to a variety of metabolites. Only a very small amount is nonenzymatically hydrolyzed to inactive products.

Clinical Use

Tiotropium is the dithienyl derivative of N-methyl scopolamine, a quaternary analogue of naturally occurring scopolamine in Atropa belladonna. It is indicated primarily for the relief of bronchospasms associated with COPD and can be considered to be a site-specific, local medication to the lung.

Side effects

Tiotropium has an adverse reaction profile similar to that of ipratropium, with dry mouth being the most common adverse effect; however, blurred vision, tachycardia, urinary difficulty, headache precipitation, and exacerbation of narrow-angle glaucoma have been reported.

Synthesis

At least two synthetic paths have been disclosed in the patent and literature. The synthesis of tiotropium is depicted in the scheme. Tropenol hydrochloride 209 was first neutralized with ammonia in toluene and then the free base was reacted with methyl di-(2- thienyl)glycolate (210) in the presence of sodium hydride to furnish desired tropenol ester 211 in 83% yield. The vanadium-catalyzed oxidation of tropenol ester 211 using hydrogen peroxide-urea complex gave epoxide 212, which was converted into its quaternary salt 25 with methyl bromide. The last two steps were carried out in a one-pot process in 88%yield.

Related news

ORIGINAL ARTICLEInvestigation of the efficacy of generic and brand-name Tiotropium bromide (cas 136310-93-5) in the management of chronic obstructive pulmonary disease: A randomized comparative trial09/07/2019

Introduction: The beneficial effects of tiotropium bromide, a long acting anticholinergic bronchodilator, in the management of chronic obstructive pulmonary disease have been shown in previous studies. The present study aimed to compare the efficacy and safety of generic (Tiova®) and brand-name ...detailed

Original articleAsthma, lower airway diseasesEffect of Tiotropium bromide (cas 136310-93-5) on airway remodeling in a chronic asthma model09/06/2019

BackgroundRecent evidence suggests that acetylcholine acting through muscarinic receptors may play an inhibitory role in the mechanisms that drive the structural changes in the airways called airway remodeling. The novel anticholinergic drug tiotropium bromide, which selectively antagonizes musc...detailed

Tiotropium bromide (cas 136310-93-5) inhibits relapsing allergic asthma in BALB/c mice☆09/03/2019

Recurrent relapses of allergic lung inflammation in asthmatics may lead to airway remodeling and lung damage. We tested the efficacy of tiotropium bromide, a selective long-acting, muscarinic receptor antagonist as an adjunct therapy in relapses of allergic asthma in mice. We compared the effect...detailed

Original articleComparison of the rapid effects of single inhalations of formoterol and Tiotropium bromide (cas 136310-93-5) on respiratory function and COPD symptoms in a randomized crossover study09/02/2019

BackgroundThis study aimed to compare rapid improvements in respiratory function and symptoms following single inhalation of formoterol (FOM) dry power inhaler (DPI) or tiotropium bromide (TIO) DPI in patients with chronic obstructive pulmonary disease (COPD).detailed

Effects of Tiotropium bromide (cas 136310-93-5) on airway hyperresponsiveness and inflammation in mice exposed to organic dust09/01/2019

IntroductionAcute exposure to organic dust (OD) in pig barns induces intense airway inflammation with neutrophilia and hyperresponsiveness. This reaction is likely associated with increased cholinergic activity. Therefore, the involvement of cholinergic mechanisms in the reaction to acute exposu...detailed

Evaluation of patients’ real-world post-dispensing use and storage environments of Tiotropium bromide (cas 136310-93-5) Respimat® soft mist inhaler on its in vitro dose delivery and lung deposition08/31/2019

BackgroundOral inhalation is the main drug delivery route for treating obstructive lung conditions. Thus, many inhaler devices with various design and pharmaceutical formulation have been introduced. The fine particle dose (FPD) and mass median aerodynamic diameter (MMAD ≤ 5 μm) of the aerosol...detailed

Pharmacological characterization of the interaction between Tiotropium bromide (cas 136310-93-5) and olodaterol on human bronchi and small airways08/30/2019

Combining a long-acting β2-agonist (LABA) with a long-acting muscarinic antagonist (LAMA) is the cornerstone to treat patients with chronic obstructive pulmonary disease (COPD). In this study we have characterized the interaction between the LAMA tiotropium bromide, and the LABA olodaterol, on ...detailed