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Tiotropium bromide

CAS No.
136310-93-5
Chemical Name:
Tiotropium bromide
Synonyms
TiotropiuM broMide anhydrous;(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;(1R,2R,4S,5S,7s)-7-(2-Hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-diMethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-iuM broMide;(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;Tiova;Ba-679;BA 79BR;Spiriva
CBNumber:
CB4244930
Molecular Formula:
C19H22BrNO4S2
Molecular Weight:
472.42
MDL Number:
MFCD00867027
MOL File:
136310-93-5.mol
MSDS File:
SDS
Last updated:2024-11-21 17:11:28

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
CAS DataBase Reference 136310-93-5(CAS DataBase Reference)
FDA UNII XX112XZP0J
ATC code R03BB04,R03BB54

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS07
Signal word  Danger
Hazard statements  H360-H315-H319
Precautionary statements  P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
HS Code  2942.00.0500
NFPA 704
0
2 0

Tiotropium bromide price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical T3032 Tiotropium Bromide >98.0%(HPLC)(T) 136310-93-5 50mg $129 2024-03-01 Buy
TCI Chemical T3032 Tiotropium Bromide >98.0%(HPLC)(T) 136310-93-5 200mg $323 2024-03-01 Buy
Cayman Chemical 15773 Tiotropium (bromide) ≥98% 136310-93-5 1mg $73 2024-03-01 Buy
Cayman Chemical 15773 Tiotropium (bromide) ≥98% 136310-93-5 5mg $141 2024-03-01 Buy
Cayman Chemical 15773 Tiotropium (bromide) ≥98% 136310-93-5 25mg $431 2024-03-01 Buy
Product number Packaging Price Buy
T3032 50mg $129 Buy
T3032 200mg $323 Buy
15773 1mg $73 Buy
15773 5mg $141 Buy
15773 25mg $431 Buy

Tiotropium bromide Chemical Properties,Uses,Production

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.

Description

Tiotropium is an antagonist that binds to M1, M2, and M3 muscarinic acetylcholine receptors (Kds = 0.43, 0.54, and 0.69 nM, respectively, for human receptors). It decreases acetylcholine-induced contraction of isolated guinea pig trachea in a concentration-dependent manner. In vivo, tiotropium (1 g/L inhaled aerosol) confers complete protection against acetylcholine-induced bronchospasms in anesthetized dogs. Formulations containing tiotropium have been used in the treatment of chronic obstructive pulmonary disease (COPD).

Chemical Properties

White Solid

Originator

Boehringer lngelheim (Germany)

Uses

Anti - Asthmatic

Uses

Specially selective choline drug resistance

Uses

Muscarinic receptor antagonist. Bronchodilator

Definition

ChEBI: An organic bromide salt having (1alpha,2beta,4beta,5alpha,7beta)-7-[(hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]non ne as the counterion. Used (in the form of the hydrate) for maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease.

brand name

Spiriva

General Description

Tiotropium bromide, (1 ,2 ,4 ,7 )-7-[(hydroxidi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane, (Spiriva) is anantimuscarinic agent that is used in an inhalation device to deliverthe drug into the lungs. It is indicated in the treatment ofchronic obstructive pulmonary disease (COPD), includingchronic bronchitis and emphysema. The standard once-dailydose is 18 g of tiotropium.

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.

Synthesis_136310-93-5

storage

Store at +4°C

Tiotropium bromide Preparation Products And Raw materials

Global( 440)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8810 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2472 58
Hebei Kingfiner Technology Development Co.Ltd
+86-15532196582 +86-15373005021 lisa@kingfinertech.com China 3010 58
Zibo Hangyu Biotechnology Development Co., Ltd
+86-0533-2185556 +8617865335152 Mandy@hangyubiotech.com China 10986 58
Hebei Ganmiao New material Technology Co., LTD
+86-17332992504 +86-17332992504 sales8@hbganmiao.com China 300 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106 sales@frappschem.com China 880 50
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 FandaChem@Gmail.com China 9087 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479 sales@fine-chemtech.com CHINA 885 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32957 60

View Lastest Price from Tiotropium bromide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tiotropium bromide pictures 2024-12-13 Tiotropium bromide
136310-93-5
US $0.00-0.00 / g 1g 99% 100kg/month WUHAN FORTUNA CHEMICAL CO., LTD
Tiotropium bromide pictures 2024-11-21 Tiotropium bromide
136310-93-5
US $9.90 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
Tiotropium bromide pictures 2024-11-19 Tiotropium bromide
136310-93-5
US $45.00-77.00 / mg 99.09% 10g TargetMol Chemicals Inc.

Tiotropium bromide Spectrum

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)- (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 Ba-679 BR otropiuM broMide (1R,2S,4R,5S,7R)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-diMethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-iuM broMide TiotropiuM BroMide(Spiriva, BA 679BR) (1α,2β,4β,5α,7β)-7-[(2-Hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-diMethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane 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), (1a,2b,4b,5a,7b)- TiopropiuM TIOTROPIUM BROMIDE Tiotropium bromide, >=99% Tiotropium Bromide Impurity 8 rel-(1R,2R,4S,5S,7s)-7-(2-Hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium bromide Thiamethoxam bromide USP Tiotropium bromide Tiotropium bromide USP/EP/BP Tiotropium Bromide Impurity 6 Tiotropium bromideQ: What is Tiotropium bromide Q: What is the CAS Number of Tiotropium bromide Q: What is the storage condition of Tiotropium bromide Q: What are the applications of Tiotropium bromide (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 (1R,2R,4S,5S,7s)-7-(2-Hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-diMethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-iuM broMide TiotropiuM broMide anhydrous (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 (1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide (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 BA 79BR Spiriva Tiova Tiotropium Bromide (100 mg) 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)- 136310-93-5 C19H22BrNO4S2H2O C19H22NO4S2Br C19H21BrNO4S2 stock for supply, stable production, we can also offer commerical quantity Tiotropium Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds API 136310-93-5