[(2S)-3-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-2-hydroxypropyl](propan-2-yl)amine hydrochloride

• ChemBase ID: 179714
• Molecular Formular: C18H30ClNO3
• Molecular Mass: 343.8887
• Monoisotopic Mass: 343.19142151
• SMILES: C1CC1COCCc1ccc(OC[C@H](CNC(C)C)O)cc1.Cl
• Canonical SMILES: O[C@H](COc1ccc(cc1)CCOCC1CC1)CNC(C)C.Cl
• InChI: InChI=1S/C18H29NO3.ClH/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16;/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3;1H
• InChIKey: CHDPSNLJFOQTRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-3-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-2-hydroxypropyl](propan-2-yl)amine hydrochloride
• IUPAC Traditional name: [(2S)-3-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-2-hydroxypropyl](propan-2-yl)amine hydrochloride
• Synonyms: Levobetaxolol hydrochloride; Betaxolol Hydrochloride

Database IDs

• CAS Number: 116209-55-3
• PubChem SID: 164235624
• PubChem CID: 60656

CALCULATED PROPERTIES

• Acid pKa: 14.087972
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.65399736
• LogD (pH = 7.4): 0.31399572
• Log P: 2.5392344
• Molar Refractivity: 88.6396 cm^3
• Polarizability: 35.132854 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: beta 1 -Adrenoceptor antagonist

Product Information

• Salt Data: HCl
• Application(s): Antianginal; Antihypertensive agent; Used to control intraocular pressure

REFERENCES

• Ger. Pat., 1977, Synthelabo, 2 649 605; CA, 87, 134543j, (synth, tox)
• Cadigan, P.J. et al., Br. J. Clin. Pharmacol., 1980, 9, 569, (pharmacol)
• Morselli, P.N. et al., L.E.R.S. Monogr. Ser., Vol. 1, 1983, (book)
• Pascard, C. et al., Acta Cryst. C, 1984, 40, 1430, (cryst struct)
• Vermeij, P., Pharm. Weekbl., 1984, 119, 1198, (rev)
• Beresford, R. et al., Drugs, 1986, 31, 6, (rev)
• Manoury, P.M. et al., J. Med. Chem., 1987, 30, 1003, (synth, pharmacol, isomers)
• Buckley, M.M.-T. et al., Drugs, 1990, 40, 75, (rev)
• Olsen, L. et al., J. Chromatogr., 1993, 636, 231, (hplc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 630
• Jira, T. et al., Pharmazie, 1993, 48, 829, (hplc, resoln)
• Beta-blockers in Clinical Practice, (Eds. Cruickshank, J.M. et al), 2nd edn., Churchill Livingstone, 1994, 1080, (book)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6750, (synonyms)
• Di Bono, G. et al., Synthesis, 1995, 699, (S-form)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, KEA350