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

• ChemBase ID: 170709
• Molecular Formular: C13H10ClN3O5S2
• Molecular Mass: 387.8186
• Monoisotopic Mass: 386.97504012
• SMILES: c12c(C(=C(N(S1(=O)=O)C)C(=O)Nc1cc(ccn1)O)O)sc(c2)Cl
• Canonical SMILES: Oc1ccnc(c1)NC(=O)C1=C(O)c2sc(cc2S(=O)(=O)N1C)Cl
• InChI: InChI=1S/C13H10ClN3O5S2/c1-17-10(13(20)16-9-4-6(18)2-3-15-9)11(19)12-7(24(17,21)22)5-8(14)23-12/h2-5,19H,1H3,(H2,15,16,18,20)
• InChIKey: UCAKXZIBERZGOW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-4-hydroxy-N-(4-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ^6,5,2-thieno[2,3-e][1λ^6,2]thiazine-3-carboxamide
• IUPAC Traditional name: 6-chloro-4-hydroxy-N-(4-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-1λ^6,5,2-thieno[2,3-e][1λ^6,2]thiazine-3-carboxamide
• Synonyms: 6-Chloro-4-hydroxy-N-(5-hydroxy-2-pyridinyl)-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-Dioxide; 5-Hydroxy Lornoxicam

Database IDs

• CAS Number: 123252-96-0
• PubChem SID: 164226619
• PubChem CID: 71749094

CALCULATED PROPERTIES

• Acid pKa: 1.9241424
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.3362839
• LogD (pH = 7.4): -1.4614853
• Log P: 0.4647603
• Molar Refractivity: 89.879 cm^3
• Polarizability: 34.09505 Å^3
• Polar Surface Area: 119.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Greenish Yellow Solid
• Melting Point: >195°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H943880

The main metabolite of Lornoxicam (L470000) in plasma and synovial fluid.

REFERENCES

• Balfour, J., et al.: Drugs, 51, 639 (1996)
• Bonnabry, P., et al.: Eur. J. Clin. Pharmacol., 49, 305 (1996)
• Miners, J., et al.: Br. J. Clin. Pharmacol., 45, 525 (1996)
• Ieiri, I., et al.: Ther. Drug Monit., 22, 237 (1996)
• Iida, I., et al.: Drug Metab. Di