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

• ChemBase ID: 177901
• Molecular Formular: C13H11N3O4S2
• Molecular Mass: 337.37414
• Monoisotopic Mass: 337.01909785
• SMILES: c1ccc2c(c1)C(=C(N(S2(=O)=O)C)C(=O)Nc1nccs1)O
• Canonical SMILES: O=C(C1=C(O)c2ccccc2S(=O)(=O)N1C)Nc1nccs1
• InChI: InChI=1S/C13H11N3O4S2/c1-16-10(12(18)15-13-14-6-7-21-13)11(17)8-4-2-3-5-9(8)22(16,19)20/h2-7,17H,1H3,(H,14,15,18)
• InChIKey: SYCHUQUJURZQMO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2-methyl-1,1-dioxo-N-(1,3-thiazol-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC Traditional name: sudoxicam
• Synonyms: 4-Hydroxy-2-methyl-N-2-thiazolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; N-(2-Thiazolyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; CP 15973; NSC 615046; Sudoxicam

Database IDs

• CAS Number: 34042-85-8
• PubChem SID: 164233811
• PubChem CID: 54682951

CALCULATED PROPERTIES

• Acid pKa: 4.3364563
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.2284067
• LogD (pH = 7.4): -1.6758454
• Log P: 0.95472056
• Molar Refractivity: 83.5686 cm^3
• Polarizability: 31.406069 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brown Solid
• Melting Point: 240-243°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S688950

Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.

REFERENCES

• Wiseman, E., et al.: Biochem. Pharmacol., 21, 2323 (1972)
• Schmid, J., et al.: Drug Metab. Dispos., 23, 1206 (1972)
• Marnett, L., et al.: J. Biol. Chem., 274, 22903 (1972)
• Ji, T., et al.: Chem. Res. Toxicol., 20, 701 (1972)