sodium (2R)-2-(4-{[(1S)-2-oxocyclopentyl]methyl}phenyl)propanoate

• ChemBase ID: 122601
• Molecular Formular: C15H17NaO3
• Molecular Mass: 268.28345
• Monoisotopic Mass: 268.10753869
• SMILES: C(=O)([C@@H](c1ccc(C[C@H]2C(=O)CCC2)cc1)C)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H](c1ccc(cc1)C[C@@H]1CCCC1=O)C.[Na+]
• InChI: InChI=1S/C15H18O3.Na/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16;/h5-8,10,13H,2-4,9H2,1H3,(H,17,18);/q;+1/p-1/t10-,13+;/m1./s1
• InChIKey: WORCCYVLMMTGFR-HTKOBJQYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-2-(4-{[(1S)-2-oxocyclopentyl]methyl}phenyl)propanoate
• IUPAC Traditional name: sodium (2R)-2-(4-{[(1S)-2-oxocyclopentyl]methyl}phenyl)propanoate
• Synonyms: Loxonin; Loxoprofen Sodium; sodium (R)-2-(4-(((S)-2-oxocyclopentyl)methyl)phenyl)propanoate

Database IDs

• CAS Number: 80382-23-6
• PubChem SID: 162216954
• PubChem CID: 23697607

CALCULATED PROPERTIES

• Acid pKa: 4.191381
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.0188732
• LogD (pH = 7.4): 0.3064167
• Log P: 3.345719
• Molar Refractivity: 79.6361 cm^3
• Polarizability: 26.64241 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Non-selective cyclooxygenase inhibitor; Works by reducing the synthesis of prostaglandins from arachidonic acid

Product Information

• Salt Data: Na+
• Application(s): Analgesic; Non-steroidal antiinflammatory agent

REFERENCES

• Ger. Pat., 1978, Sankyo, 2 814 556; CA, 90, 22616r, (synth, pharmacol)
• Tanaka, Y. et al., Chem. Pharm. Bull., 1983, 31, 3656, (metab)
• Terada, A. et al., J. Med. Chem., 1984, 27, 212, (synth)
• Hata, T. et al., Bull. Chem. Soc. Jpn., 1987, 60, 3535, (cryst struct)
• Naganuma, H. et al., J. Chromatogr., 1990, 530, 387, (hplc)
• Sugimoto, M. et al., Biochem. Pharmacol., 1991, 42, 2363, (pharmacol)
• Takasaki, W. et al., Chirality, 1992, 4, 308, (metab)
• Toshimasa, T. et al., J. Chromatogr., 1992, 627, 75, (hplc)
• Watanabe, T. et al., J. Toxicol. Clin. Toxicol., 1993, 31, 333, (tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 22
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, LII300