6-chloro-4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H,5H-1λ6,2-cyclopenta[e][1λ6,2]thiazine-3-carboxamide

• ChemBase ID: 172396
• Molecular Formular: C14H12ClN3O4S
• Molecular Mass: 353.78078
• Monoisotopic Mass: 353.02370456
• SMILES: C12=C(C(=C(N(S1(=O)=O)C)C(=O)Nc1ccccn1)O)CC(=C2)Cl
• Canonical SMILES: ClC1=CC2=C(C1)C(=C(N(S2(=O)=O)C)C(=O)Nc1ccccn1)O
• InChI: InChI=1S/C14H12ClN3O4S/c1-18-12(14(20)17-11-4-2-3-5-16-11)13(19)9-6-8(15)7-10(9)23(18,21)22/h2-5,7,19H,6H2,1H3,(H,16,17,20)
• InChIKey: QLSZYMHQPPZJNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H,5H-1λ^6,2-cyclopenta[e][1λ^6,2]thiazine-3-carboxamide
• IUPAC Traditional name: 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-5H-1λ^6,2-cyclopenta[e][1λ^6,2]thiazine-3-carboxamide
• Synonyms: 6-Chloro-4-hydroxy-2-methyl-N-2-pyridinyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-Dioxide; Chlortenoxicam; Ro 13-9297; TS 110; Telos; Xefo; Xefocam; Lornoxicam

Database IDs

• CAS Number: 70374-39-9
• PubChem SID: 164228306
• PubChem CID: 54742539

CALCULATED PROPERTIES

• Acid pKa: 6.688514
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.46144924
• LogD (pH = 7.4): -0.28973013
• Log P: 0.50139767
• Molar Refractivity: 90.2461 cm^3
• Polarizability: 32.931267 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Yellow Solid
• Melting Point: 216-219°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L470000

Cyclooxygenase inhibitor; structurally similar to Tenoxicam. Anti-inflammatory; analgesic.

REFERENCES

• Ankier, S.I., et al.: Postgrad. Med. J., 64, 752 (1988)
• Tricerri, M., et al.: Chem. Phys. Lipids, 71, 61 (1988)
• Santos, N., et al.: Biochemistry, 37, 8674 (1988)
• Pellicano, A., et al.: Infect. Immun., 75, 1738 (1988)