106133-20-4 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.
Check Digit Verification of cas no
The CAS Registry Mumber 106133-20-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,1,3 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 106133-20:
(8*1)+(7*0)+(6*6)+(5*1)+(4*3)+(3*3)+(2*2)+(1*0)=74
74 % 10 = 4
So 106133-20-4 is a valid CAS Registry Number.
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
106133-20-4Relevant articles and documents
Continuous-Flow Synthesis of (R)-Tamsulosin Utilizing Sequential Heterogeneous Catalysis
Ishitani, Haruro,Kobayashi, Shū,Laroche, Benjamin,Nishizawa, Ken,Saito, Yuki
, (2022/02/16)
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 crystal form
-
Paragraph 0017-0020, (2021/05/26)
The invention relates to the technical field of preparation of crystal forms of organic compounds, in particular to a preparation method of a tamsulosin hydrochloride crystal form. The method comprises the following steps: completely dissolving tamsulosin in a solvent at 60-70 DEG C, then dropwise adding acid for reaction for a period of time, conducting cooling to 20-30 DEG C, and conducting filtering, washing and drying to obtain tamsulosin, wherein tamsulosin is a refined product. The method is simple in process, high in yield, high in product purity and suitable for large-scale industrialization.
A high optical purity of tamsulosin preparation method of leach
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Paragraph 0037; 0040; 0043; 0044; 0045; 0046; 0049, (2018/10/02)
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.