Tamsulosin

Base Information

• Chemical Name: Tamsulosin
• CAS No.: 106133-20-4
• Molecular Formula: C20H28N2O5S
• Molecular Weight: 444.98
• Hs Code.: 2935009090
• European Community (EC) Number: 600-716-9
• UNII: G3P28OML5I
• DSSTox Substance ID: DTXSID3023631
• Nikkaji Number: J340.699G
• Wikipedia: Tamsulosin
• Wikidata: Q418480
• NCI Thesaurus Code: C75055
• RXCUI: 77492
• Pharos Ligand ID: 214LGSBKMYMF
• Metabolomics Workbench ID: 43015
• ChEMBL ID: CHEMBL836
• Mol file: 106133-20-4.mol

Synonyms:5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide;Flomax;LY 253352;LY-253352;tamsulosin;tamsulosin hydrochloride;YM 617;YM-617

Chemical Property of Tamsulosin

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Melting Point: 226-228 °C
• Refractive Index: 1.553
• Boiling Point: 595.5 °C at 760 mmHg
• PKA: 10.08±0.60(Predicted)
• Flash Point: 313.9 °C
• PSA: 108.26000
• Density: 1.191 g/cm³
• LogP: 4.51290
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 408.17189317
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)-propyl)-2-methoxybenzenesulfonamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Benign Prostatic Hypertrophy Agents
• Canonical SMILES: CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
• Isomeric SMILES: CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
• Recent ClinicalTrials: Effect of Preoperative Tamsulosin on Postoperative Urinary Retention
• Recent EU Clinical Trials: The effect of tamsulosin on the spontaneous passage of bile stones
• Recent NIPH Clinical Trials: Efficacy of Tamsulosin plus Tadalafil versus Tamsulosin as medical expulsive therapy for lower ureteric stones: A randomized controlled trial
• Description: Tamsulosin hydrochloride is the first in the class of potent and selective α- 1A adrenoceptor antagonists introduced for the treatment of dysuria associated with benign prostatic hypertrophy (BPH). In a clinical study, significant improvement in irritative and obstructive symptoms has been reported for tamsulosin treated patients with BPH. ln vitro studies in human penile erectile tissue and vas deferens indicated that tamsulosin may be of use in treating male sexual dysfunction.
• Uses: tamsulosin chemotherapy drug
• Therapeutic Function: Antihypertensive

Technology Process of Tamsulosin

There total 82 articles about Tamsulosin 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: 89.8%

(+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (112244-38-9) + 2-(o-ethoxyphenoxy)-ethyl bromide (3259-03-8) → (R)-tamsulosin (106133-20-4,106138-88-9)

Guidance literature:

In N-methyl-acetamide; water;

Reference yield: 86.0%

(R)-tamsulosin-(S)-BPA salt → (R)-tamsulosin (106133-20-4,106138-88-9)

Guidance literature:

With ammonia; In water; at 45 - 50 ℃; for 0.5h; pH=10.5; Product distribution / selectivity;

Reference yield: 76.5%

5-[(R)-2-[[2-(2-ethoxyphenoxy)ethyl][(R)-1-phenylethyl]amino]propyl]-2-methoxybenzenesulfonamide → (R)-tamsulosin (106133-20-4,106138-88-9)

Guidance literature:

With methanol; palladium 10% on activated carbon; ammonium formate; at 20 ℃; Reagent/catalyst; Temperature;

upstream raw materials:

2-(2-ethoxyphenoxy)acetaldehyde

(S)-5-(2-hydroxypropyl)-2-methoxybenzenesulfonamide

(R)-5-(2-azidopropyl)-2-methoxybenzenesulfonamide

(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate

Downstream raw materials:

tamsulosin hydrochloride

(R)-tamsulosin maleate salt

(R)-tamsulosin

(R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulphonamide adipate

Refernces

• 1、 -. "Preparation method of tamsulosin hydrochloride". . . Retrieved 2021/05/22.
• 2、 -. "Preparation method of tamsulosin hydrochloride". Paragraph 0041; 0046-0047. . Retrieved 2020/07/13.