N-{4-[(1S)-1-hydroxy-2-[(propan-2-yl)amino]ethyl]phenyl}methanesulfonamide hydrochloride

• ChemBase ID: 179711
• Molecular Formular: C12H21ClN2O3S
• Molecular Mass: 308.82474
• Monoisotopic Mass: 308.09614122
• SMILES: S(=O)(=O)(Nc1ccc(cc1)[C@H](CNC(C)C)O)C.Cl
• Canonical SMILES: CC(NC[C@@H](c1ccc(cc1)NS(=O)(=O)C)O)C.Cl
• InChI: InChI=1S/C12H20N2O3S.ClH/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17;/h4-7,9,12-15H,8H2,1-3H3;1H
• InChIKey: VIDRYROWYFWGSY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(1S)-1-hydroxy-2-[(propan-2-yl)amino]ethyl]phenyl}methanesulfonamide hydrochloride
• IUPAC Traditional name: N-{4-[(1S)-1-hydroxy-2-[(propan-2-yl)amino]ethyl]phenyl}methanesulfonamide hydrochloride
• Synonyms: Sotalol Hydrochloride

Database IDs

• CAS Number: 30236-32-9
• PubChem SID: 164235621
• PubChem CID: 9796652

CALCULATED PROPERTIES

• Acid pKa: 10.069403
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.138338
• LogD (pH = 7.4): -2.1217964
• Log P: -0.395064
• Molar Refractivity: 71.1191 cm^3
• Polarizability: 28.832848 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Beta-Adrenergic blocker; Potassium channel (K VR ) blocker

Product Information

• Salt Data: HCl
• Application(s): Antiarrhythmic agent

REFERENCES

• Uloth, R.H. et al., J. Med. Chem., 1966, 9, 88, (synth)
• Gartiez, D.A. et al., J. Pharm. Sci., 1972, 61, 1728, (ms)
• Gadret, M. et al., Acta Cryst. B, 1976, 32, 2757, (cryst struct)
• Schnelle, K., Adv. Clin. Pharmacol., 1978, 18, 111, (rev, props, anal)
• Gomoll, A.W. et al., Eur. J. Pharmacol., 1986, 132, 123, (pharmacol, isom)
• Singh, B.N. et al., Drugs, 1987, 34, 311, (rev, pharmacol)
• Am. J. Cardiol., Suppl., 1990, 89, 1A, (rev, pharmacol)
• Foster, R.T. et al., Anal. Profiles Drug Subst., 1992, 21, 573, (rev, sotalol)
• Singh, B.N. et al., J. Cardiovasc. Pharmacol., 1992, 20, S75, (rev, sotalol)
• Touboul, P., Eur. Heart J., 1993, 14, 24, (sotalol, dexsotalol)
• Funck-Brentano, C., Eur. Heart J., 1993, 14, 30, (sotalol, dexsotalol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 640
• Hohnloser, S.H. et al., N. Engl. J. Med., 1994, 331, 31, (rev)
• Advani, S. et al., Drugs, 1995, 49, 664, (dexsotalol, rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCK250