106133-20-4

Basic information

• Product Name: Tamsulosin
• Synonyms: 5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulfonamide;TAMSOLUSIN;TAMSULOSIN;TAMSULOSINE;(R)(-)5-[2-[2-(2-Ethoxyphenoxy)ethyl]amino-propyl]-2-methoxybenzenesulfonmidehydrochloride;TamsulosinRHCl;TANSULOSIN;Amsulosin
• CAS NO: 106133-20-4
• Molecular Formula: C₂₀H₂₈N₂O₅S
• Molecular Weight: 408.51
• EINECS: 1533716-785-6
• Product Categories: Tamsulosin;API
• Mol File: 106133-20-4.mol
• Article Data: 41

Chemical Properties

• Melting Point: 226-228°C
• Boiling Point: 595.5 °C at 760 mmHg
• Flash Point: 313.9 °C
• Appearance: White crystals
• Density: 1.191 g/cm³
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 10.08±0.60(Predicted)
• CAS DataBase Reference: Tamsulosin(CAS DataBase Reference)
• NIST Chemistry Reference: Tamsulosin(106133-20-4)
• EPA Substance Registry System: Tamsulosin(106133-20-4)

Safety Data

• Hazardous Substances Data: 106133-20-4(Hazardous Substances Data)

Usage

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.

Originator

Yamanouchi (Japan)

Uses

Different sources of media describe the Uses of 106133-20-4 differently. You can refer to the following data:
1. tamsulosin
2. chemotherapy drug

Manufacturing Process

In 1,000 ml of acetonitrile was suspended 17 g of 5-{2-[2-(2- ethoxyphenoxy)ethylamino]-1-hydroxy-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride and while stirring the suspension, 9 g of thionyl chloride was added dropwise to the suspension at room temperature, whereby the product first dissolved and then began to crystallize gradually. After stirring the mixture for two days, the crystals formed were recovered by filtration, washed with chloroform and dried to provide 15 g of 5-{1-chloro-2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride. Melting point: 197°-200°C.In methanol was dissolved the 5-{1-chloro-2-[2-(2- ethoxyphenoxy)ethylamino]ethyl}-2-methoxybenzenesulfonamide hydrochloride and after adding thereto 10% palladium carbon, dechlorination was performed under hydrogen stream at normal temperature and pressure. The palladium carbon was filtered away and the filtrate was concentrated under reduced pressure to provide the 2-methoxy-5-{2-[2-(2- ethoxyphenoxy)ethylamino]ethyl}benzenesulfonamide hydrochloride, which was recrystallized from 120 ml of a mixture of methanol and ethanol (1:4 by volume ratio) to provide the colorless crystals thereof. The melting point of the 5-{2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride: 254°-256°C.

Brand name

Harnal

Therapeutic Function

Antihypertensive

General Description

Tamsulosin (Flomax), a nonquinazoline benzensulfonamide,is the first in the class of subtype selective 1Ablocker.It is many folds more selective for α1A-receptorsthan for the other α1-receptors. This selectivity may favorblockade of α1A-receptors found in the prostate gland overthose found in vascular tissue. Tamsulosin is efficacious inthe treatment of BPH with little effect on blood pressure.Orthostatic hypotension is not as great with this agent aswith the nonselective quinazolines.

InChI:InChI=1/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1

Upstream product

• 112101-81-2 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide 
• 112244-38-9 (+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 80223-79-6 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride 
• 116091-63-5 2-methoxy-5-(2-oxopropyl)benzenesulfonamide 
• 6781-16-4 (2-ethoxyphenoxy)methyl cyanide 
• 94-71-3 2-Ethoxyphenol 
• 104-01-8 4-Methoxyphenylacetic acid 
• 94666-07-6 5-[2-[2-(2-ethoxyphenoxy)-ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide 
• 169506-15-4 2-(2-ethyloxyphenoxy)ethyl methanesulfonate 
• 3250-73-5 2-(2-ethoxyphenoxy)ethanol 
• 116091-64-6 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride 
• 3259-03-8 2-(o-ethoxyphenoxy)-ethyl bromide 
• 842130-16-9 (R)-2-(N-(trifluoroacetyl)arnino)-1-(4'-methoxy-3'-sulphamoyl)-phenylpropane 

Downstream Products

• 106133-20-4 tamsulosin hydrochloride 
• 106133-20-4 (R)-tamsulosin 
• 1312673-07-6 (R)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulphonamide adipate 
• 882494-15-7 (R)-tamsulosin fumarate salt 
• 853947-68-9 (R)-tamsulosin maleate salt 
• 853913-61-8 (R)-tamsulosin(+)-tartrate salt 
• 133261-19-5 tamsulosin hydrochloride 
• 521300-99-2 (R)-tamsarocin (-)-camphor-10-sulfonate 

Related news

Tamsulosin (cas 106133-20-4) attenuates abdominal aortic aneurysm growth07/23/2019

BackgroundTamsulosin, an α1A-adrenergic receptor inhibitor, is prescribed to treat benign prostatic hyperplasia in men >60 years of age, the same demographic most susceptible to abdominal aortic aneurysm. The goal of this study was to investigate the effect of tamsulosin on abdominal aortic ane...detailed

The AAHKS Clinical Research Award: Prophylactic Tamsulosin (cas 106133-20-4) Does Not Reduce the Risk of Urinary Retention Following Lower Extremity Arthroplasty: A Double-Blinded Randomized Controlled Trial07/22/2019

BackgroundPostoperative urinary retention (POUR) is common. Selective alpha-1 adrenergic antagonists, such as tamsulosin, are effective for treating urinary retention. The purpose of this study is to determine whether perioperative prophylactic tamsulosin reduces the incidence of POUR following ...detailed

Relevant articles and documents

Continuous-Flow Synthesis of (R)-Tamsulosin Utilizing Sequential Heterogeneous Catalysis

We describe the continuous-flow synthesis of (R)-tamsulosin, a blockbuster therapeutic drug employed for dysuria associated with urinary stones and benign prostatic hyperplasia, by utilizing sequential heterogeneous catalysis. Two heterogeneous catalysts have been developed for the synthesis, and the key step involves reductive amination of nitriles using dimethylpolysilane-modified Pd on activated carbon/calcium phosphate. Overall, (R)-tamsulosin was obtained in 60 % yield and 64 % ee (99 % ee after recrystallization) in a flow stream through four catalytic transformations without the need for the isolation or purification of any intermediates or byproduct.

Preparation method of tamsulosin hydrochloride

The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of tamsulosin hydrochloride. The preparation method comprises the following steps: firstly reacting benzenesulfonamide as shown in a formula (II) with bromo ether as shown in a formula (III) to obtain a condensation compound intermediate as shown in a formula (IV), carrying out transfer hydrogenation reaction on the intermediate as shown in the formula (IV) in the presence of ammonium formate and a catalyst to obtain R-tamsulosin free alkali as shown in a formula (V), subjecting the R-tamsulosin free alkali and hydrochloric acid to a salt forming reaction in an organic solvent, so that the tamsulosin hydrochloride shown in the formula (I) is obtained. The method is characterized in that the reaction of the formula (II) and the formula (III) is carried out in a solvent containing water. According to the synthesis route disclosed by the invention, in the reaction process of the obtained tamsulosin hydrochloride, no disubstituted by-product generated by reaction of bimolecular bromide and amine exists, the obtained tamsulosin hydrochloride has the advantages of good product purity, stable quality and high yield, and the synthesis method disclosed by the invention is mild in reaction condition and convenient to synthesize.

A high optical purity of tamsulosin preparation method of leach

The invention discloses a preparation method of tamsulosin hydrochloride with high optical purity, and belongs to a medicine technology and a chemical field. A recrystallization method is adopted, crude products of (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl phenyl sulfonamide hydrochloride are refined, so that pure products of the (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl group sulfonamide hydrochloride of which the e.e. value is larger than 99.8% is obtained; a crystallizing solvent adopted by the recrystallization method is a mixed solvent consisting of an organic solvent and water, the organic solvent is selected from one of methanol, ethyl alcohol, acetone, acetonitrile and isopropyl alcohol, and the recrystallization temperature is under 15 DEG C. The preparation method disclosed by the invention is simple to operate, short in period, low in cost and good in repeatability, and can solve the inevitable problem of rework for treatment in the industrial production.