| Identification | Back Directory | [Name]
N-acetyl-2-carboxy Benzenesulfonamide | [CAS]
849067-18-1 | [Synonyms]
ADVANFQVCYCSNR-UHFFFAOYSA-N
N-acetyl-2-carboxy Benzenesulfonamide
Benzoic acid, 2-[(acetylamino)sulfonyl]-
N-acetyl-2-carboxy Benzenesulfonamide Exclusive | [Molecular Formula]
C9H9NO5S | [MDL Number]
MFCD12912280 | [MOL File]
849067-18-1.mol | [Molecular Weight]
243.24 |
| Chemical Properties | Back Directory | [Melting point ]
178-180 °C | [density ]
1.463±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
2.79±0.36(Predicted) |
| Hazard Information | Back Directory | [Description]
N-acetyl-2-carboxy Benzenesulfonamide is a structural analog of aspirin that acts as a non-selective inhibitor of cyclooxygenase (COX) with a COX-2 selectivity index of 0.23. In vitro studies showed that N-acetyl-2-carboxy Benzenesulfonamide is a more potent inhibitor of COX-1/COX-2 with IC50 values of 0.06 μM and 0.25 μM, respectively, than aspirin with IC50 values of 0.35 μM and 2.4 μM, respectively. | [Uses]
N-Acetyl-2-carboxybenzenesulfonamide is an orally active COX-1 and COX-2 inhibitor with IC50s of 0.06 μM and 0.25 μM, respectively. N-Acetyl-2-carboxybenzenesulfonamide shows anti-inflammatory activity[1]. | [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]. | [IC 50]
0.06 and 0.25 μm for cox-1 and cox-2, respectively | [References]
[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). |
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