106138-88-9

Basic information

• Product Name: (+)-Tamsulosin
• Synonyms: Benzenesulfonamide, 5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, (S)- (9CI)
• CAS NO: 106138-88-9
• Molecular Formula: C20H28 N2 O5 S
• Molecular Weight: 408.51
• Mol File: 106138-88-9.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 595.5°Cat760mmHg
• Flash Point: 313.9°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: (+)-Tamsulosin(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Tamsulosin(106138-88-9)
• EPA Substance Registry System: (+)-Tamsulosin(106138-88-9)

Safety Data

• Hazardous Substances Data: 106138-88-9(Hazardous Substances Data)

Usage

General Description

(+)-Tamsulosin is a medication classified as an alpha-adrenergic blocker and is used to treat symptoms of an enlarged prostate, also known as benign prostatic hyperplasia (BPH). It works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate. The chemical is a selective antagonist of alpha1A adrenergic receptors in the lower urinary tract, which leads to a reduction in smooth muscle tone in the prostate and bladder neck. It is commonly prescribed to improve symptoms such as difficulty urinating, weak stream, and the need to urinate frequently or urgently. It is typically taken orally and is available in both immediate-release and extended-release formulations. Some common side effects of (+)-Tamsulosin include dizziness, headache, and nasal congestion.

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-/m0/s1

Upstream product

• 852619-17-1 C₂₀H₂₆N₂O₅S 
• 116091-64-6 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride 
• 3259-03-8 2-(o-ethoxyphenoxy)-ethyl bromide 
• 3250-73-5 2-(2-ethoxyphenoxy)ethanol 
• 169506-15-4 2-(2-ethyloxyphenoxy)ethyl methanesulfonate 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 104-01-8 4-Methoxyphenylacetic acid 
• 80223-79-6 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride 
• 94-71-3 2-Ethoxyphenol 
• 131029-02-2 (S)-1-(4-methoxyphenyl)propan-2-yl acetate 
• 131029-01-1 (S)-(+)-1-(4-methoxyphenyl)propan-2-ol 
• 937018-21-8 (S)-1-(3-(chlorosulfonyl)-4-methoxyphenyl)propan-2-yl acetate 
• 937018-23-0 (S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate 
• 937018-25-2 (R)-5-(2-azidopropyl)-2-methoxybenzenesulfonamide 

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.

Method of resolving tamsulosin enantiomer

The invention relates to a method of resolving tamsulosin enantiomer, and in particular, relates to a method of resolving tamsulosin, represented as the formula (I), into an R-enantiomer and an S-enantiomer. The method includes the steps of: (a) dissolving a solid mixture of (R)-tamsulosin free alkali and (S)-tamsulosin free alkali in a solvent and performing a reaction to the free alkalis with camphor-10-sulfonic acid to form a solution containing a pair of diastereomeric camphor-10-sulfonates of tamsulosin, and then preferentially precipitating one diastereomeric camphor-10-sulfonate of the tamsulosin from the solution containing a pair of the diastereomeric camphor-10-sulfonates of tamsulosin, thereby forming a precipitate, in which one diastereomer is enriched, and a solute, in which the other one diastereomer is enriched; and (b) from one of the precipitate and the solute, releasing tamsulosin free alkali to obtain optical-rotation-enriched tamsulosin free alkali. The method has excellent technical performance.

Novel Pharmaceutical Forms, and Methods of Making and Using the Same

Crystalline salts, polymorphs, solvates, and hydrates of bicalutamide, 5-fluorouracil, donepezil, anastrozole, nelfinavir, mirtazapine, lansoprazole, and tamsulosin, or derivatives thereof are provided by the subject invention. Methods of making and using the same are also provided.