Tamsulosin hydrochloride

Iupac Name：5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide;hydrochloride

Molecular Weight：408.51200

Introduction: Tamsulosin 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. View more+

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1. Names and Identifiers

1.1 Name: Tamsulosin hydrochloride
1.2 Synonyms: (-)-(R)-5-[2-[[2-(o-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide monohydrochloride (R)-(-)-5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzolsulfonamid hydrochloride (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochloride (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochloride ee (R)-5-[2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide monohydrochloride (R)-Tamsulosin (R)-TAMSULOSIN HCL (R)-Tamsulosin Hydrochloride (R)-TAMSULOSIN HYDROCHLORIDE,WHITE TO OFF-WHITE SOLID (S)-5-(2-((2-(2-ethoxyphenoxy)ethyl)aMino)propyl)-2-MethoxybenzenesulfonaMide 5-[(2R)-2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-benzenesulfonamidehydrochloride 5-[(2R)-2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride 5-[(2R)-2-{[2-(2-éthoxyphénoxy)éthyl]amino}propyl]-2-méthoxybenzènesulfonamide chlorhydrate 5-[(2R)-2-{[2-(2-Ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonamide hydrochloride (1:1) 5-[(2R)-2-{[2-(2-Ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzolsulfonamidhydrochlorid 5-[(R)-2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]]-2-methoxybenzenesulfonamide Hydrochloride Benzenesulfonamide, 5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, hydrochloride (1:1) benzenesulfonamide, 5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, monohydrochloride FLOMAX Flomax hydrochloride HARNAL MFCD00922997 Omic OMNIC PRADIF TAMSOLUSIN HCL TAMSOLUSIN HYDROCHLORIDE Tamsulosin (hydrochloride) Tamsulosin HCl TAMSULOSIN HYDRCHLORIDE Tamsulosin Hydrochloride (200 mg) TAMSULOSIN HYDROCHLORIDE , CERTIFIED REFERENCE MATERIAL TaMsulosin Hydrochloride, EP TAMSULOSINE HYDROCHLORIDE TAMSULOSINHCL UNII:11SV1951MR YM 12617-1 YM-617 Yutana Yutanal

1.3 CAS No.: 106463-17-6

1.4 CID: 5362376

1.5 EINECS(EC#): 617-011-7

1.6 Molecular Formula: C20H29ClN2O5S (isomer)

1.7 Inchi: InChI=1S/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/t15-;/m1./s1

1.8 InChkey: ZZIZZTHXZRDOFM-XFULWGLBSA-N

1.9 Canonical Smiles: CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N.Cl

1.10 Isomers Smiles: CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N.Cl

2. Properties

3.1 Melting point: 228-230ºC

3.1 Boiling point: 595.5ºC at 760 mmHg

3.1 Flash Point: 313.9ºC

3.1 Vapour pressure: 3.79E-14mmHg at 25°C

3.1 Precise Quality: 408.17200

3.1 PSA: 108.26000

3.1 logP: 4.51290

3.1 Solubility: DMSO: >10mg/mL

3.2 Appearance: white to off-white solid

3.3 Chemical Properties: White to Off-White Solid

3.4 Water Solubility: DMSO: >10mg/mL

3.5 StorageTemp: 2-8°C

3. Use and Manufacturing

4.1 Storage: Ambient temperatures.

4.2 Usage: Specific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy

4. Safety and Handling

5.1 Symbol: GHS07

5.1 Hazard Codes: Xn

5.1 Signal Word: Warning

5.1 Risk Statements: 22-36/37/38

5.1 Safety Statements: 26

5.1 Hazard Declaration: H302-H315-H319-H335

5.1 RIDADR: NONH for all modes of transport

5.1 Caution Statement: P301 + P312 + P330-P305 + P351 + P338

5.1 WGK Germany: 3

5.1 RTECS: DB2430000

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

View all

6. Synthesis Route

106463-17-6Total: 1 Synthesis Route

852619-17-1

106463-17-6 267 Suppliers

106133-20-4 185 Suppliers

Literatures:
EP2172443 A1, ; Page/Page column 12 ;
Yield: null

7. Other Information

7.0 Merck: 14,9049

7.1 Description: Tamsulosin 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.

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

7.3 Chemical Properties: White to Off-White Solid

7.4 Uses: Specific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy.

7.5 Uses: antineoplastic, alkylating agent

7.6 Uses: (R)-Tamsulosin is a specific α1-adrenoceptor antagonist. It is used in the treatment of benign prostatic hypertrophy.

7.7 Uses: An α1-adrenoceptor antagonist

7.8 Uses: Specific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy

7.9 Hazard: Moderately toxic by ingestion.

7.10 Usage: An alpha-1 adrenoceptor antagonist

7.11 Description: Tamsulosin 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.

7.12 Description: Tamsulosin is a potent antagonist of α₁-adrenergic receptors (α₁-ARs; K_i = 0.229 nM in a radioligand binding assay). It is 3,800-fold selective for α₁-ARs over α₂-ARs (K_i = 871 nM). Tamsulosin antagonizes norepinephrine-induced contraction of isolated rabbit aorta (pA₂ = 10.11) but has no effect on contraction stimulated by histamine, serotonin (Item No. 14332), angiotensin II (Item No. 17150), or prostaglandin F_2α (Item No. 16010). 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.

7.13 Originator: Contiflo OD,Ranbaxy Laboratories,India

7.14 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.

7.15 Therapeutic Function: Antihypertensive

7.16 General Description: Tamsulosin 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.

8. Computational chemical data

Molecular Weight：408.51200g/mol
Molecular Formula：C₂₀H₂₉ClN₂O₅S
Compound Is Canonicalized：True
XLogP3-AA：
Exact Mass：444.1485709
Monoisotopic Mass：444.1485709
Complexity：539
Rotatable Bond Count：11
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：7
Topological Polar Surface Area：108
Heavy Atom Count：29
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：2

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