4-hydroxy-2-methyl-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxamide

• ChemBase ID: 166678
• Molecular Formular: C10H10N2O4S
• Molecular Mass: 254.2624
• Monoisotopic Mass: 254.03612781
• SMILES: c1cccc2c1C(=C(N(S2(=O)=O)C)C(=O)N)O
• Canonical SMILES: NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C
• InChI: InChI=1S/C10H10N2O4S/c1-12-8(10(11)14)9(13)6-4-2-3-5-7(6)17(12,15)16/h2-5,13H,1H3,(H2,11,14)
• InChIKey: BBOFTHBIXOWDMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2-methyl-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC Traditional name: 4-hydroxy-2-methyl-1,1-dioxo-1λ^6,2-benzothiazine-3-carboxamide
• Synonyms: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; Piroxicam Impurity C; Despyridyl Piroxicam (Piroxicam Impurity C)

Database IDs

• CAS Number: 24683-25-8
• PubChem SID: 162260811
• PubChem CID: 54692128

CALCULATED PROPERTIES

• Acid pKa: 4.952833
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.2832079
• LogD (pH = 7.4): -2.927825
• Log P: -0.6295667
• Molar Refractivity: 62.4318 cm^3
• Polarizability: 23.989527 Å^3
• Polar Surface Area: 100.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D297415

Piroxicam impurity C; and also a metabolite of Meloxicam.

REFERENCES

• Zinnes, H., et al.: J. Med. Chem., 16, 44 (1973)
• Schmid, J., et al.: Xenobiotica, 25, 1219 (1973)