5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide hydrochloride

• ChemBase ID: 155796
• Molecular Formular: C20H29ClN2O5S
• Molecular Mass: 444.97266
• Monoisotopic Mass: 444.14857072
• SMILES: CCOc1ccccc1OCCN[C@H](C)Cc1ccc(c(c1)S(=O)(=O)N)OC.Cl
• Canonical SMILES: CCOc1ccccc1OCCN[C@@H](Cc1ccc(c(c1)S(=O)(=O)N)OC)C.Cl
• 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
• InChIKey: ZZIZZTHXZRDOFM-XFULWGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide hydrochloride
• IUPAC Traditional name: tamsulosin hydrochloride; 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide hydrochloride
• Synonyms: 5-[(2R)-2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride; Tamsulosin hydrochloride; 5-[(2R)-2-[[2-(-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide Hydrochloride; Flomax; Harnal; Omnic; Pradif; YM 12617-1; YM 617; Yutanal; (R)-Tamsulosin Hydrochloride; (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochloride

Database IDs

• CAS Number: 106463-17-6
• MDL Number: MFCD00922997
• PubChem SID: 162249934
• PubChem CID: 5362376

CALCULATED PROPERTIES

• Acid pKa: 9.932656
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.6416307
• LogD (pH = 7.4): 0.46680295
• Log P: 2.038114
• Molar Refractivity: 108.8649 cm^3
• Polarizability: 43.42021 Å^3
• Polar Surface Area: 99.88 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; Methanol
• Apperance: white powder; White to Off-White Solid
• Melting Point: 228-230°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Prostate selective alpha 1-adrenoceptor antagonist

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: HCl
• Application(s): Antineoplastic agent; Used in the treatment of benign prostatic hyperplasia
• Empirical Formula (Hill Notation): C20H28N2O5S · HCl

DETAILS

Sigma Aldrich - T1330

Biochem/physiol Actions
Tamsulosin 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.1

Toronto Research Chemicals - T006350

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

REFERENCES

• Kawabe, K., et al.: J. Urol., 144, 908 (1990)
• Abrams, P., et al.: Br. J. Urol., 76, 325 (1990)
• Michel, M.C., Expert Opin. Pharmacother., 5, 151 (1990)
• Eur. Pat., 1981, Yamanouchi Pharm, 34432; CA, 96, 19812v, (synth)
• Honda, K. et al., J. Pharmacol. Exp. Ther., 1986, 239, 512; 1990, 253, 427, (pharmacol)
• Honda, K. et al., J. Pharm. Pharmacol., 1987, 39, 316
• Honda, K. et al., Naunyn-Schmiedeberg's Arch. Pharmacol., 1987, 336, 295, (pharmacol)
• Lepor, H. et al., Br. J. Pharmacol., 1988, 95, 139; 702, (activity)
• Wheeler, W.J. et al., J. Labelled Compd. Radiopharm., 1989, 27, 171, (synth)
• Yazawa, H. et al., J. Pharmacol. Exp. Ther., 1992, 263, 201, (pharmacol)
• Ratnasooriya, W.D. et al., Andrologia, 1994, 26, 107, (tox)
• Jonler, M. et al., Drugs, 1994, 47, 66, (use)
• Rabasseda, X. et al., Drugs of Today (Barcelona), 1996, 32, 259, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 951