106463-17-6

Basic information

• Product Name: Tamsulosin hydrochloride
• Synonyms: (R)-(-)-5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzolsulfonamid hydrochloride;5-[(2R)-2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-benzenesulfonamidehydrochloride;TaMsulosin Hydrochloride, EP;Tamsulosin Hydrochloride (200 mg);5-[(R)-2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]]-2-methoxybenzenesulfonamide Hydrochloride;(S)-5-(2-((2-(2-ethoxyphenoxy)ethyl)aMino)propyl)-2-MethoxybenzenesulfonaMide;TAMSULOSIN HYDRCHLORIDE;Harnal,YM 617, AMsulosin
• CAS NO: 106463-17-6
• Molecular Formula: C₂₀H₂₈N₂O₅S
• Molecular Weight: 444.97
• EINECS: 1308068-626-2
• Product Categories: Tamsulosin;Adrenoceptor;Isotope Labelled Compounds;MUSTARDGEN;Active Pharmaceutical Ingredients;In treatment of benign prostatic hypertrophy;Treatment of BPH;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds
• Mol File: 106463-17-6.mol

Chemical Properties

• Melting Point: 228-230°C
• Boiling Point: 595.5 °C at 760 mmHg
• Flash Point: 313.9 °C
• Appearance: white to off-white solid
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: >10mg/mL
• Merck: 14,9049
• CAS DataBase Reference: Tamsulosin hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tamsulosin hydrochloride(106463-17-6)
• EPA Substance Registry System: Tamsulosin hydrochloride(106463-17-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: DB2430000
• Hazardous Substances Data: 106463-17-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tamsulosin hydrochloride is used as a specific α1-adrenoceptor antagonist for the treatment of benign prostatic hypertrophy. It helps reduce urinary obstruction and relieves symptoms associated with symptomatic BPH by blocking α1-adrenoceptors in the prostate, prostatic capsule, prostatic urethra, and bladder neck, leading to the relaxation of smooth muscles in these areas.
Used in Antineoplastic Applications:
Tamsulosin hydrochloride is also used as an antineoplastic and alkylating agent, demonstrating potential therapeutic effects in cancer treatment.
Used in Drug Delivery Systems:
Innovative drug delivery systems are being developed to enhance the applications and efficacy of Tamsulosin hydrochloride, particularly in the treatment of cancer. These systems aim to improve the delivery, bioavailability, and therapeutic outcomes of the drug by employing various organic and metallic nanoparticles as carriers.

References

https://www.drugbank.ca/drugs/DB00706 https://en.wikipedia.org/wiki/Tamsulosin

Originator

Contiflo OD,Ranbaxy Laboratories,India

Therapeutic Function

Antihypertensive

Hazard

Moderately toxic by ingestion.

Biological Activity

Selective α 1A -adrenoceptor antagonist (pK i values are 9.97, 9.64 and 8.86 for α 1A , α 1B and α 1D subtypes respectively). Decreases resting maximal urethral pressure with negligable effect on mean arterial blood pressure in vivo .

Biochem/physiol Actions

Tamsulosin is an α1A/1D-adrenoceptor antagonist used as a treatment of benign prostatic hypertrophy (BPH). Its activity as an ? blocker also affects the iris, and has led to complications during cataract surgery, a condition called "floppy iris" syndrome.

InChI:InChI=1/C20H28N2O5S.ClH/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);1H

Synthetic route

(S)-tamsulosin-(R)-BPA salt → (+)-Tamsulosin (106463-17-6)

Conditions	Yield
With ammonia In water at 45 - 50℃; for 0.5h; pH=10.5; Product distribution / selectivity;	83.4%

(R/S)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide D-10-camphorsulfonic acid salt → (+)-Tamsulosin (106463-17-6) + (R)-tamsulosin (106133-20-4)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water

oxalate salt of tamsulosin (882494-06-6) + (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (35193-63-6, 35193-64-7, 39648-67-4, 50574-52-2) → (R)-tamsulosin-(S)-BPA salt + (+)-Tamsulosin (106463-17-6)

Conditions	Yield
In water; acetone at 27 - 55℃; for 5.41667h; Product distribution / selectivity;

(S)-tamsulosin-(S)-BPA salt → (+)-Tamsulosin (106463-17-6)

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

C20H26N2O5S (852619-17-1) → (+)-Tamsulosin (106463-17-6) + (R)-tamsulosin (106133-20-4)

Conditions	Yield
Stage #1: C20H26N2O5S; (S)-chloro[(1,2,3,4-η)-pentamethyl-2,4-cyclopentadien-1-yl] [N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamidato-κN1,κN2]iridium In acetonitrile at -3 - 3℃; for 0.5h; Stage #2: With formic acid; triethylamine In acetonitrile at -3 - 20℃;	A n/a B n/a

(+)-Tamsulosin (106463-17-6) → (+)-Tamsulosin hydrochloride

Conditions	Yield
With hydrogenchloride In methanol at 45℃; Product distribution / selectivity;	77.5%

(R)-10-camphorsulfonic acid (35963-20-3) + (+)-Tamsulosin (106463-17-6) + (R)-tamsulosin (106133-20-4) → (R)-tamsarocin (-)-camphor-10-sulfonate (521300-99-2)

Conditions	Yield
Stage #1: (R)-10-camphorsulfonic acid; (+)-Tamsulosin; (R)-tamsulosin In water; acetone at 20℃; for 20 - 24h; Stage #2: Stage #3: at 20℃;

Upstream product

• 882494-06-6 oxalate salt of tamsulosin 
• 35193-63-6 (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 
• 852619-17-1 C₂₀H₂₆N₂O₅S 
• 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 

Downstream Products

• 80223-99-0 (+)-Tamsulosin hydrochloride 
• 521300-99-2 (R)-tamsarocin (-)-camphor-10-sulfonate 

Related news

Development and optimization of a novel oral controlled delivery system for Tamsulosin hydrochloride (cas 106463-17-6) using response surface methodology08/04/2019

The purpose of this study was to develop and optimize oral controlled-release formulations for tamsulosin hydrochloride using a combination of two cellulose ester derivatives, hydroxypropyl methylcellulose (HPMC) and hydroxypropyl methylcellulose phthalate (HPMCP), with Surelease® as a coating m...detailed

Preparation and evaluation of Tamsulosin hydrochloride (cas 106463-17-6) sustained-release pellets modified by two-layered membrane techniques08/03/2019

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Spectrophotometric estimation of Tamsulosin hydrochloride (cas 106463-17-6) by acid-dye method07/31/2019

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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 FOR PRODUCING OPTICALLY ACTIVE AMINE

The present invention provides a method for producing chiral amines, comprising asymmetric transfer hydrogenation of imine compounds in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand. The present invention is useful for production of chiral amines in an efficient manner in terms of their optical and chemical yields.

Process for the resolution of racemic (R,S) -5-(2-(2-(2- ethoxyphenoxy) ethylamino)propyl)-2-methoxybenzene sulfonamide (tamsulosin), its novel R and S isomers and their salts and processes for their preparation

An improved process is described to resolve a racemic mixture in any proportion of 5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxy benzene sulfonamide as a free base or some of its salts, with BPA either S or R form to obtain enantiomerically highly pure R and S-isomer as a well characterized free base or as a salt of the title compound. Also described are novel R and S-isomers of 5-(2-(2-(2-ethoxyphenoxy) ethylamino)propyl)-2-methoxy benzene sulfonamide and their salts and the processes for their preparation.

Process for the separation of R(-)-and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide

The process for separating the R(?)- and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-sulfonamide enantiomers comprises (a) reacting a mixture of said enantiomers with an optically active organic acid to form diastereoisomeric salts with said enantiomers, where in said diastereoisomeric salts have different solubility and can be separated by crystallization; (b) separating the diastereoisomeric salt mixture enriched in the salt of one of the enantiomers; and (c) releasing said salts to obtain the R(?)or S(+) enantiomer. The R(?)-5-[2-[[2-(2-ethoxyphenoxy) ethyl]amino]propyl]-2-methoxybenzenesulfonamide enantiomer has α-adrenergic blocking activity and is useful as an antihypertensive agent suitable for the treatment of congestive heart failure and benign prostatic hypertrophy.