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

• ChemBase ID: 171873
• Molecular Formular: C13H15NO5S
• Molecular Mass: 297.3269
• Monoisotopic Mass: 297.06709359
• SMILES: c1cccc2c1C(=C(N(S2(=O)=O)C)C(=O)OC(C)C)O
• Canonical SMILES: CC(OC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C)C
• InChI: InChI=1S/C13H15NO5S/c1-8(2)19-13(16)11-12(15)9-6-4-5-7-10(9)20(17,18)14(11)3/h4-8,15H,1-3H3
• InChIKey: ZHWSBDIYCSOTBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl 4-hydroxy-2-methyl-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• IUPAC Traditional name: isopropyl 4-hydroxy-2-methyl-1,1-dioxo-1λ^6,2-benzothiazine-3-carboxylate
• Synonyms: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic Acid 1-Methylethyl Ester1,1-Dioxide; 1-Methylethyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide; NSC 640233; Piroxicam Impurity L; Isopropyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity L)

Database IDs

• CAS Number: 118854-48-1
• PubChem SID: 164227783
• PubChem CID: 54686201

CALCULATED PROPERTIES

• Acid pKa: 4.500482
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.29540938
• LogD (pH = 7.4): -1.2326126
• Log P: 1.3299862
• Molar Refractivity: 74.5461 cm^3
• Polarizability: 29.04811 Å^3
• Polar Surface Area: 83.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I824600

Piroxicam Impurity L. Also an impurity found in meloxicam (M216100).

REFERENCES

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