4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxamide

• ChemBase ID: 157732
• Molecular Formular: C14H13N3O5S
• Molecular Mass: 335.33512
• Monoisotopic Mass: 335.05759153
• SMILES: Cc1cc(no1)NC(=O)C1=C(c2ccccc2S(=O)(=O)N1C)O
• Canonical SMILES: Cc1onc(c1)NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C
• InChI: InChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)
• InChIKey: YYUAYBYLJSNDCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC Traditional name: isoxicam; 4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide
• Synonyms: Isoxicam; isoxicam; 伊索昔康

Database IDs

• CAS Number: 34552-84-6
• EC Number: 252-084-5
• MDL Number: MFCD00079374
• PubChem SID: 24895947; 162251869
• PubChem CID: 54677972

CALCULATED PROPERTIES

• Acid pKa: 4.359653
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.39166653
• LogD (pH = 7.4): -1.8514644
• Log P: 0.77024204
• Molar Refractivity: 85.7921 cm^3
• Polarizability: 31.372087 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: DL0703000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Gene Information: human ... PTGS1(5742), PTGS2(5743)
• Mechanism of Action: Prostaglandin antagonist

Product Information

• Grade: analytical standard
• Salt Data: Free Base
• Application(s): Analgesic; Antiinflammatory; Antipyretic agent
• Empirical Formula (Hill Notation): C14H13N3O5S

REFERENCES

• DiPasquale, G. et al., Agents Actions, 1975, 5, 256, (pharmacol)
• Zinnes, H. et al., J. Med. Chem., 1982, 25, 12, (synth, pharmacol)
• Yakatan, G.J., Semin. Arthritis Rheum., 1982, 12, 153, (rev)
• DiPasquale, G., Drugs of Today (Barcelona), 1983, 19, 119, (rev)
• Borondy, P.E. et al., Drug Metab. Dispos., 1984, 12, 444, (metab)
• Svoboda, J. et al., Coll. Czech. Chem. Comm., 1986, 51, 1133, (synth)
• Dalla Croce, P. et al., J. Chem. Res., Synop., 1986, 150, (synth)
• Woolf, T.F. et al., Drug Metab. Dispos., 1989, 17, 662, (metab, exp)
• Woolf, T.F. et al., Eur. J. Drug Metab. Pharmacokinet., 1992, 17, 21, (metab, human)
• Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (pKa, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 21