Tamsulosin hydrochloride

Base Information

• Chemical Name: Tamsulosin hydrochloride
• CAS No.: 106463-17-6
• Deprecated CAS: 112101-78-7,128332-25-2
• Molecular Formula: C20H29ClN2O5S
• Molecular Weight: 408.519
• Hs Code.: 29350090
• European Community (EC) Number: 629-756-5
• UNII: 11SV1951MR
• DSSTox Substance ID: DTXSID2046628
• Wikidata: Q27108379
• NCI Thesaurus Code: C29486
• RXCUI: 236495
• ChEMBL ID: CHEMBL1200914
• Mol file: 106463-17-6.mol

Synonyms:Benzenesulfonamide,5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-,monohydrochloride (9CI);Benzenesulfonamide,5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, monohydrochloride,(R)-;(-)-YM 12617;(R)-(-)-YM 12617;Flomax;Harnal;LY 253351;Omic;Omnic;YM 12617-1;YM 617;Yutanal;Tamsulosin HCl;

Chemical Property of Tamsulosin hydrochloride

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Melting Point: 228-230 °C
• Boiling Point: 595.5 °C at 760 mmHg
• Flash Point: 313.9 °C
• PSA: 108.26000
• LogP: 4.51290
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: >10mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 444.1485709
• Heavy Atom Count: 29
• Complexity: 539

Purity/Quality:

99% ^*data from raw suppliers

(R)-TamsulosinHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N.Cl
• Isomeric SMILES: CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N.Cl
• Recent ClinicalTrials: Investigating Medication vs. Prostatic Urethral Lift: Assessment and Comparison of Therapies for BPH
• Recent EU Clinical Trials: Impact of selective alpha 1A receptor antagonists on the pupil size after instillation of tropicamide 0.5% and phenylephrine 10%
• Recent NIPH Clinical Trials: Evaluation of the combination effects of silodosin and dutasteride in patients with urination disorders associated with benign prostatic hyperplasia
• 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. 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 , angiotensin II , or prostaglandin F2α . 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.
• Uses: Specific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy Specific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy. antineoplastic, alkylating agent (R)-Tamsulosin is a specific α1-adrenoceptor antagonist. It is used in the treatment of benign prostatic hypertrophy. An α1-adrenoceptor antagonist
• Therapeutic Function: Antihypertensive

Technology Process of Tamsulosin hydrochloride

There total 14 articles about Tamsulosin hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.4%

(S)-tamsulosin-(R)-BPA salt → (+)-Tamsulosin (106463-17-6,106138-88-9)

Guidance literature:

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

Reference yield:

C20H26N2O5S (852619-17-1) → (+)-Tamsulosin (106463-17-6,106138-88-9) + (R)-tamsulosin (106133-20-4,106138-88-9)

Guidance literature:

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;

With formic acid; triethylamine; In acetonitrile; at -3 - 20 ℃;

Reference yield:

(R/S)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide D-10-camphorsulfonic acid salt → (+)-Tamsulosin (106463-17-6,106138-88-9) + (R)-tamsulosin (106133-20-4,106138-88-9)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water;

upstream raw materials:

oxalate salt of tamsulosin

(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

C₂₀H₂₆N₂O₅S

2-(2-ethoxyphenoxy)ethanol

Downstream raw materials:

(+)-Tamsulosin hydrochloride

(R)-tamsarocin (-)-camphor-10-sulfonate

Refernces

• 1、 -. "METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE". Page/Page column 12. . Retrieved 2010/04/25.
• 2、 -. "Process for the separation of R(-)-and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide". Page 6; Sheet 3. . Retrieved 2010/02/10.