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

• ChemBase ID: 178066
• Molecular Formular: C20H29ClN2O5S
• Molecular Mass: 444.97266
• Monoisotopic Mass: 444.14857072
• SMILES: c1c(c(ccc1C[C@@H](NCCOc1ccccc1OCC)C)OC)S(=O)(=O)N.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-;/m0./s1
• InChIKey: ZZIZZTHXZRDOFM-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide hydrochloride
• IUPAC Traditional name: tamsulosin hydrochloride
• Synonyms: 5-[(2S)-2-[[2-(-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide Hydrochloride; (+)-LY 253352; (+)-YM 617; S-(+)-YM 12617; YM 12617-2; (S)-Tamsulosin Hydrochloride

Database IDs

• CAS Number: 106463-19-8
• PubChem SID: 164233976
• PubChem CID: 60146

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

DETAILS

Toronto Research Chemicals - T006355

Specific α1-adrenoceptor antagonist. 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)