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

• ChemBase ID: 166543
• Molecular Formular: C14H11N3O4S
• Molecular Mass: 317.31984
• Monoisotopic Mass: 317.04702685
• SMILES: c1cccc2c1C(=C(NS2(=O)=O)C(=O)Nc1ncccc1)O
• Canonical SMILES: O=C(C1=C(O)c2c(S(=O)(=O)N1)cccc2)Nc1ccccn1
• InChI: InChI=1S/C14H11N3O4S/c18-13-9-5-1-2-6-10(9)22(20,21)17-12(13)14(19)16-11-7-3-4-8-15-11/h1-8,17-18H,(H,15,16,19)
• InChIKey: XRXYFCIBSPQECM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC Traditional name: 4-hydroxy-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• Synonyms: 4-Hydroxy-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; Piroxicam Impurity B; Desmethyl Piroxicam (Piroxicam Impurity B)

Database IDs

• CAS Number: 65897-46-3
• PubChem SID: 162260676
• PubChem CID: 54719424

CALCULATED PROPERTIES

• Acid pKa: 4.757072
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.19917448
• LogD (pH = 7.4): -1.8290678
• Log P: 0.37258515
• Molar Refractivity: 82.1468 cm^3
• Polarizability: 30.804243 Å^3
• Polar Surface Area: 108.39 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292185

Piroxicam impurity B.

REFERENCES

• Chiaini, J., et al.: J. Med. Chem., 14, 1175 (1971)
• Kwon, S., et al.: Arzneim.-Forsch., 46, 966 (1971)