ChemicalBook > CAS DataBase List > Tiotropium bromide

Tiotropium bromide

Product Name
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
Formula Weight
472.42
MOL File
136310-93-5.mol
More
Less

Tiotropium bromide Property

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)
More
Less

Safety

HS Code 
2942.00.0500
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H360May damage fertility or the unborn child

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

More
Less

N-Bromosuccinimide Price

TCI Chemical
Product number
T3032
Product name
Tiotropium Bromide
Purity
>98.0%(HPLC)(T)
Packaging
50mg
Price
$129
Updated
2024/03/01
TCI Chemical
Product number
T3032
Product name
Tiotropium Bromide
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$323
Updated
2024/03/01
Cayman Chemical
Product number
15773
Product name
Tiotropium (bromide)
Purity
≥98%
Packaging
1mg
Price
$73
Updated
2024/03/01
Cayman Chemical
Product number
15773
Product name
Tiotropium (bromide)
Purity
≥98%
Packaging
5mg
Price
$141
Updated
2024/03/01
Cayman Chemical
Product number
15773
Product name
Tiotropium (bromide)
Purity
≥98%
Packaging
25mg
Price
$431
Updated
2024/03/01
More
Less

Tiotropium bromide Chemical Properties,Usage,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

Muscarinic receptor antagonist. Bronchodilator

Uses

Specially selective choline drug resistance

Uses

Anti - Asthmatic

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.

storage

Store at +4°C

Tiotropium bromide Preparation Products And Raw materials

Raw materials

Methyl 2,2-dithienylglycolate Sodium Dichloromethane Methyl bromide

Preparation Products

More
Less

Tiotropium bromide Suppliers

Brazil 1 Canada 2 China 352 Europe 1 France 1 Germany 1 India 33 Israel 1 Italy 3 Japan 1 South Korea 1 Switzerland 1 United Kingdom 8 United States 34 Global 440
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32161
Advantage
58
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63687
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38631
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
CarboMer, Inc.
Tel
--
Fax
--
Email
sales@carbomer.com
Country
United States
ProdList
4026
Advantage
67
BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
SynFine Research
Tel
--
Fax
--
Email
research@synfine.com
Country
United States
ProdList
1024
Advantage
68
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Bio-Era Research Chemicals Inc
Tel
--
Fax
--
Country
United States
ProdList
49
Advantage
58
Interchem Corporation USA
Tel
--
Fax
--
Email
esa@interchem.com
Country
United States
ProdList
469
Advantage
58
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
Cerilliant Corporation
Tel
--
Fax
--
Email
techserv@cerilliant.com
Country
United States
ProdList
1629
Advantage
69
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
Ibis Chemie International
Tel
--
Fax
--
Email
pinakin@satyam.net.in
Country
United States
ProdList
83
Advantage
51
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
More
Less

View Lastest Price from Tiotropium bromide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Tiotropium bromide 136310-93-5
Price
US $0.00-0.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg/month
Release date
2021-06-25
Hebei Weibang Biotechnology Co., Ltd
Product
Tiotropium bromide 136310-93-5
Price
US $9.90/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-21
Baoji Guokang Bio-Technology Co., Ltd.
Product
Tiotropium bromide 136310-93-5
Price
US $158.00/g/Bag
Min. Order
1g
Purity
99
Supply Ability
100kg
Release date
2021-06-05

136310-93-5, Tiotropium bromideRelated Search:

Dimethyl sulfate Allyl bromide Rocuronium bromide Ethidium bromide Dimethyl disulfide Sodium bromate Thifensulfuron methyl Tetrahydrothiophene Dimethyl phthalate Dimethyl carbonate Thianaphthene Vecuronium bromide OXITROPIUM BROMIDE N,N-Dimethylformamide Cephalothin sodium ETHANE Dimidium bromide 2-Thiophenecarboxaldehyde

  • (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
  • Ba-679 BR
  • otropiuM broMide
  • TiotropiuM broMide anhydrous
  • (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
  • (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
  • 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
  • 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