Basic information
- CAS
106463-17-6- Standard SMILES
CCOc1ccccc1OCCN[C@H](C)Cc1ccc(OC)c(S(N)(=O)=O)c1.Cl- InChIKey
ZZIZZTHXZRDOFM-XFULWGLBSA-N- Molecular formula
- C20H29ClN2O5S
- Average molar mass
- 445 g/mol
- Monoisotopic mass
- 444.14857071
Overview
Tamsulosin hydrochloride is a hydrochloride resulting from the reaction of equimolar amounts of tamulosin and hydrogen chloride. It has a role as an antineoplastic agent and an alpha-adrenergic antagonist. It contains a tamsulosin(1+). It is an enantiomer of an ent-tamsulosin hydrochloride.
Names & identifiers
- Preferred name
- Tamsulosin Hydrochloride
- IUPAC
- 5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide;hydrochloride
- English name
- Tamsulosin hydrochloride
- Molecular formula
- C20H29ClN2O5S
- Molecular weight
- 444.97
Names & synonyms
TAMSULOSIN HYDROCHLORIDE106463-17-6Tamsulosin HClHarnalPradifYM617LY253351R-(-)-YM-12617DTXSID2046628Flomax MRYM-12617-1LY-253351
Show more names
SOY ISOFLAVONEFLOMAX(R)-(-)-5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzolsulfonamid hydrochloride(R)-TaMsulosinTAMSULOSIN HYDRCHLORIDETaMsulosin hydrochlorid(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochlorideOmicOMNIC
11SV1951MR(-)-(R)-5-(2-((2-(o-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide monohydrochlorideR-(-)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochlorideCHEBI:9399DTXCID0026628Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, monohydrochloride, (R)-JALYN COMPONENT TAMSULOSIN HYDROCHLORIDEDiffundox
Database identifiers
- CAS
106463-17-6
Properties
Computed structural properties
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 11
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 539
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 228 · 228-230°C
- alpha
- 24 · D24 -4.0° (c = 0.35 in methanol)
- RTECS
- 2430000 · DB2430000
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL · DMSO: >10mg/mL
- form
- white powder
- color
- White to Off-White
- Merck
- 14 · 14,9049
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- ZZIZZTHXZRDOFM-XFULWGLBSA-N
- SMILES
- C1(S(=O)(=O)N)=CC(=CC=C1OC)C[C@@H](C)NCCOC1C=CC=CC=1OCC.Cl |&1:13,r|
- CAS DataBase Reference
- 106463 · 106463-17-6(CAS DataBase Reference)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 133 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (99.2%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Tamsulosin hydrochloride
vLess-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- hs_code
- 29350090
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
TAMSULOSIN HYDROCHLORIDE
Adrenergic alpha-Antagonists [MoA]; alpha-Adrenergic Blocker [EPC]
MeSH Pharmacological Classification
Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.
Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.
Applications
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.
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 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.
UsesSpecific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy
UsesSpecific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy.
Related reactions
6 records
Compound notes
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