Abstract
Compound 7, N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide, showed in vitro (whole blood assay) a strong inhibitory activity on the two cyclooxygenase (COX) enzymes (IC(50)(COX-1) = 2.2 microM and IC(50)(COX-2) = 0.4 microM), being more active but less COX-2-selective than nimesulide. Physicochemical studies and structural analyses indicated that the anionic sulfonamidate species seemed to be the active form of methanesulfonamides, which optimally interacted with the COX enzymes' active sites.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aminopyridines / chemistry*
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Aminopyridines / pharmacology
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Animals
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Anions
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Binding Sites
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Crystallography, X-Ray
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Cyclooxygenase 1
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Cyclooxygenase 2
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors / chemistry*
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Cyclooxygenase Inhibitors / pharmacology
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Edema / drug therapy
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Humans
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In Vitro Techniques
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Isoenzymes / antagonists & inhibitors*
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Membrane Proteins
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Prostaglandin-Endoperoxide Synthases
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Rats
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Rats, Wistar
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Spectrophotometry, Infrared
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Sulfonamides / chemistry*
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Sulfonamides / pharmacology
Substances
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Aminopyridines
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Anions
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Anti-Inflammatory Agents, Non-Steroidal
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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Isoenzymes
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Membrane Proteins
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N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide
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Sulfonamides
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Cyclooxygenase 1
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Cyclooxygenase 2
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PTGS1 protein, human
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PTGS2 protein, human
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Prostaglandin-Endoperoxide Synthases
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Ptgs1 protein, rat
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nimesulide