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

• ChemBase ID: 168597
• Molecular Formular: C11H11NO5S
• Molecular Mass: 269.27374
• Monoisotopic Mass: 269.03579346
• SMILES: c1cccc2c1C(=C(NS2(=O)=O)C(=O)OCC)O
• Canonical SMILES: CCOC(=O)C1=C(O)c2c(S(=O)(=O)N1)cccc2
• InChI: InChI=1S/C11H11NO5S/c1-2-17-11(14)9-10(13)7-5-3-4-6-8(7)18(15,16)12-9/h3-6,12-13H,2H2,1H3
• InChIKey: KHQMRIBGVBXDMI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• IUPAC Traditional name: ethyl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• Synonyms: 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylic Acid Ethyl Ester 1,1-Dioxide; Piroxicam Impurity H; Ethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide(Piroxicam Impurity H)

Database IDs

• CAS Number: 24683-21-4
• PubChem SID: 162262729
• PubChem CID: 54678723

CALCULATED PROPERTIES

• Acid pKa: 4.3999877
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.4363715
• LogD (pH = 7.4): -1.9958488
• Log P: 0.6897352
• Molar Refractivity: 65.2306 cm^3
• Polarizability: 25.396992 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E918850

Piroxicam Impurity H.

REFERENCES

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