Tiotropium bromide monohydrate

Base Information

• Chemical Name: Tiotropium bromide monohydrate
• CAS No.: 139404-48-1
• Molecular Formula: C19H22BrNO4S2^.xH2O
• Molecular Weight: 472.424
• Hs Code.: 2934999090
• European Community (EC) Number: 629-840-1,690-508-4
• UNII: L64SXO195N
• ChEMBL ID: CHEMBL3545181
• DSSTox Substance ID: DTXSID30904820
• NCI Thesaurus Code: C61974
• RXCUI: 1298831
• Wikidata: Q27114833
• Mol file: 139404-48-1.mol

Synonyms:679 BR, BA;7-((hydroxybis(2-thienyl)acetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane bromide;BA 679 BR;BA-679 BR;BA679 BR;BR, BA 679;Bromide, Tiotropium;Spiriva;tiotropium;tiotropium bromide

Chemical Property of Tiotropium bromide monohydrate

Chemical Property:

• Melting Point: 218-220oC
• PSA: 124.77000
• LogP: -0.75580
• Solubility.: Sparingly soluble in water, soluble in methanol, practically insoluble in methylene chloride.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 489.02793
• Heavy Atom Count: 28
• Complexity: 564

Purity/Quality:

99% Min ^*data from raw suppliers

Tiotropium Bromide Monohydrate Pharmaceutical Secondary Standard; Certified Reference Material ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.O.[Br-]
• Isomeric SMILES: C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.O.[Br-]
• Recent ClinicalTrials: ANTES B+ Clinical Trial
• Recent EU Clinical Trials: A prospective multicenter placebo-controlled trial to study the efficacy and safety of Tiotropium in preventing severe asthma exacerbations in partial and uncontrolled preschool asthma. TIPP-Study
• Uses: Tiotropium Bromide hydrate is a hydrate of tiotropium bromide (Spiriva; Tiova; BA 679BR; tiopropium) that is an anticholinergic and bronchodilator and a muscarinic receptor antagonist. Although tiotropium Bromide (Spiriva; Tiova; BA 679BR; tiopropium) doe
• Clinical Use: Maintenance treatment of chronic obstructive pulmonary disease
• Drug interactions: Potentially hazardous interactions with other drugs Avoid administration with other anti-cholinergic drugs. Anti-arrhythmics: increased risk of antimuscarinic side effects with disopyramide.

Technology Process of Tiotropium bromide monohydrate

There total 27 articles about Tiotropium bromide monohydrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

N-demethyltiotropium (136310-64-0) + methyl bromide (74-83-9) → tiotropium bromide (139404-48-1)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 16h; Large scale;

Reference yield: 87.7%

N-methylsconinium hexafluorophosphate + hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8) → tiotropium bromide (139404-48-1)

Guidance literature:

N-methylsconinium hexafluorophosphate; hydroxy-di-thiophen-2-yl-acetic acid methyl ester; With potassium tert-butylate; In acetone; at 0 ℃; for 20 - 24h; Zeolite of type 4A;

With lithium bromide; In acetone; Product distribution / selectivity;

Reference yield: 85.0%

scopine methobromide → tiotropium bromide (139404-48-1)

Guidance literature:

sodium dithienylglycolate; With chloro-trimethyl-silane; 1,1'-carbonyldiimidazole; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.5h;

scopine methobromide; With 1H-imidazole; sodium hydride; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 1h;

With methanol; hydrogen bromide; In 1-methyl-pyrrolidin-2-one; acetic acid; at 0 - 20 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

N-demethyltiotropium

methyl bromide

tiotropium bromide monohydrate

hydroxy-di-thiophen-2-yl-acetic acid methyl ester

Refernces

• 1、 -. "Preparation method of tiotropium bromide". Paragraph 0075-0077. . Retrieved 2021/08/19.
• 2、 -. "A PROCESS FOR PREPARING TIOTROPIUM BROMIDE AND INTERMEDIATES THEREOF". . . Retrieved 2018/04/20.