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Home> Encyclopedia >   /  Urinary System Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate  /  Pharmaceuticals and Biochemicals
Tamsulosin hydrochloride structure
Tamsulosin hydrochloride structure

Tamsulosin hydrochloride

Iupac Name:5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide;hydrochloride
CAS No.:106463-17-6
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+
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

6. Synthesis Route
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; 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 (Item No. 14332), angiotensin II (Item No. 17150), or prostaglandin F (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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