propan-2-yl 4-hydroxy-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxylate

• ChemBase ID: 171872
• Molecular Formular: C12H13NO5S
• Molecular Mass: 283.30032
• Monoisotopic Mass: 283.05144352
• SMILES: c1cccc2c1C(=C(NS2(=O)=O)C(=O)OC(C)C)O
• Canonical SMILES: CC(OC(=O)C1=C(O)c2c(S(=O)(=O)N1)cccc2)C
• InChI: InChI=1S/C12H13NO5S/c1-7(2)18-12(15)10-11(14)8-5-3-4-6-9(8)19(16,17)13-10/h3-7,13-14H,1-2H3
• InChIKey: KCSORUCCHDBUFQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• IUPAC Traditional name: isopropyl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• Synonyms: 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylic Acid 1-Methylethyl Ester 1,1-Dioxide; 1-Methylethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide; NSC 642708; Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I)

Database IDs

• CAS Number: 76508-35-5
• PubChem SID: 164227782
• PubChem CID: 54687027

CALCULATED PROPERTIES

• Acid pKa: 4.487455
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.059166882
• LogD (pH = 7.4): -1.5411772
• Log P: 1.1063101
• Molar Refractivity: 69.6494 cm^3
• Polarizability: 27.221489 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I824575

Piroxicam impurity I.

REFERENCES

• Lombardino, J., et al.: J. Med. Chem., 14, 1171 (1971)
• Turck, D., et al.: Clin. Drug Invest., 9, 270 (1971)