Tamsulosin hydrochloride

Tamsulosin hydrochloride Basic information
Description References
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;Flomax hydrochloride;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
CAS:106463-17-6
MF:C20H29ClN2O5S
MW:444.97
EINECS:629-756-5
Product Categories:Tamsulosin;Adrenoceptor;Intermediates & Fine Chemicals;Isotope Labeled Compounds;Isotope Labelled Compounds;MUSTARDGEN;Active Pharmaceutical Ingredients;In treatment of benign prostatic hypertrophy;Treatment of BPH;Chiral Reagents;Pharmaceuticals;API;106463-17-6
Mol File:106463-17-6.mol
Tamsulosin hydrochloride Structure
Tamsulosin hydrochloride Chemical Properties
Melting point 228-230°C
alpha D24 -4.0° (c = 0.35 in methanol)
RTECS DB2430000
storage temp. 2-8°C
solubility DMSO: >10mg/mL
form white powder
color White to Off-White
Merck 14,9049
InChIKeyZZIZZTHXZRDOFM-XFULWGLBSA-N
CAS DataBase Reference106463-17-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 26
WGK Germany 3
HS Code 29350090
MSDS Information
Tamsulosin hydrochloride Usage And Synthesis
DescriptionTamsulosin hydrochloride is the hydrochloride form of Tamsulosin (Trade name: Alna ® / Flomax ®). It is a kind of medication used for the treatment of symptomatic benign prostatic hyperplasia (BPH), boosting the passage of kidney stones. It can also be used for the treatment of acute urinary retention. It is a kind of selective antagonist of alpha-1A and alpha-1B-adrenoceptros located in prostate, prostatic capsule, prostatic urethra, and bladder neck. The blockage of these receptors through Tamsulosin causes the relaxation of smooth muscles in the bladder neck and prostate.
Referenceshttps://www.drugbank.ca/drugs/DB00706
https://en.wikipedia.org/wiki/Tamsulosin
DescriptionTamsulosin is a potent antagonist of α1-adrenergic receptors (α1-ARs; Ki = 0.229 nM in a radioligand binding assay). It is 3,800-fold selective for α1-ARs over α2-ARs (Ki = 871 nM). Tamsulosin antagonizes norepinephrine-induced contraction of isolated rabbit aorta (pA2 = 10.11) but has no effect on contraction stimulated by histamine, serotonin , angiotensin II , or prostaglandin F . In vivo, tamsulosin reverses the pressor effect of phenylephrine (Item Nos. 17205 | 18619) in pithed rats. It reversibly reduces fertility in male rats when administered at a dose of 0.15 mg/kg. Tamsulosin (1-100 μg/kg) also reduces prostatic pressure in a dose-dependent manner with minimal hypotensive effects in anesthetized dogs. Formulations containing tamsulosin have been used for the treatment of benign prostatic hyperplasia.
Chemical PropertiesWhite to Off-White Solid
OriginatorContiflo OD,Ranbaxy Laboratories,India
UsesSpecific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy
UsesSpecific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy.
Usesantineoplastic, alkylating agent
Uses(R)-Tamsulosin is a specific α1-adrenoceptor antagonist. It is used in the treatment of benign prostatic hypertrophy.
UsesAn α1-adrenoceptor antagonist
DefinitionChEBI: Tamsulosin hydrochloride is a hydrochloride resulting from the reaction of equimolar amounts of tamulosin and hydrogen chloride. It has a role as an alpha-adrenergic antagonist and an antineoplastic agent. It contains a tamsulosin(1+). It is an enantiomer of an ent-tamsulosin hydrochloride.
Manufacturing ProcessIn 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.
Therapeutic FunctionAntihypertensive
General DescriptionTamsulosin hydrochloride is a subtypeselective a1A and a1D adrenoceptor antagonist, which exists in two enantiomeric forms, of which the R-isomer is the pharmaceutically active component. It is used to reduce urinary obstruction and is also involved in relieving the symptoms associated with symptomatic benign prostatic hyperplasia.
HazardModerately toxic by ingestion.
Biological ActivitySelective 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 ActionsTamsulosin 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.
storageDesiccate at RT
Tamsulosin hydrochloride Preparation Products And Raw materials
Raw materialsThionyl chloride-->Hydrogen-->Palladium hydroxide-->Benzenesulfonamide, 5-[2-[[2-(2-ethoxyphenoxy)ethyl]imino]propyl]-2-methoxy--->Tamsulosin
Topotecan hydrochloride (R)-(+)-5-(2-AMINOPROPYL)-2-METHOXYBENZENE SULFONAMIDE HYDROCHLORIDE YM617, [PHENOXY-3H]- Trinexapac-ethyl Ethanol Tamsulosin 2-(2-Methoxyphenoxy)ethylamine Tamsulosin hydrochloride (Trifluoromethoxy)benzene Sulfanilamide ISOXADIFEN-ETHYL p-Anisidine 2-Ethoxyethanol 1-AdaMantanethylaMine Ethyl acetate p-Toluenesulfonamide Diphenhydramine Hydrochloride Propyl butyrate

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