N-acetyl-2-carboxy Benzenesulfonamide

IC50: 0.06 and 0.25 μM for COX-1 and COX-2, respectively

N-acetyl-2-carboxy Benzenesulfonamide is a non-selective inhibitor of COX.

Pharmaceutical inhibition of COX is able to provide relief from the symptoms of inflammation and pain. Nonsteroidal anti-inflammatory drugs, such as aspirin, exert its effect via inhibition of COX.

In vitro: Previous in-vitro COX-1/COX-2 inhibition studies showed that N-acetyl-2-carboxy benzenesulfonamide was a more potent inhibitor than aspirin, and like aspirin. Moreover, N-acetyl-2-carboxy benzenesulfonamide was found to be a nonselective COX-2 inhibitor. In addition, the molecular modeling (docking) study demonstrated that the SO2NHCOCH3 substituent present in N-acetyl-2-carboxy benzenesulfonamide, like the acetoxy substituent in aspirin, was suitably positioned to acetylate the Ser530 hydroxyl group in the COX-2 primary binding site [1].

In vivo: Animal study showed that N-acetyl-2-carboxy benzenesulfonamide and its C-4 2,4-difluorophenyl derivative had superior antiinflammatory activity (oral dosing) in a carrageenan-induced rat paw edema assay compared to aspirin. In addition, N-acetyl-2-carboxy benzenesulfonamide and its C-4 2,4-difluorophenyl derivative exhibited comparable analgesic activity to iflunisal, and superior analgesic activity compared to aspirin [1].

Clinical trial: So far, no clinical study has been conducted.

Reference:
[1] Chen, Q. H.,Rao, P.N.P., and Knaus, E.E. Design, synthesis, and biological evaluation of N-acetyl-2-carboxybenzenesulfonamides: A novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorganic & Medicinal Chemistry 13, 2459-2468 (2005).