849067-18-1 Usage
Description
N-acetyl-2-carboxy Benzenesulfonamide is a structural analog of aspirin, characterized by its non-selective inhibition of cyclooxygenase (COX) enzymes. It demonstrates a COX-2 selectivity index of 0.23 and has been found to be a more potent inhibitor of both COX-1 and COX-2 in vitro, with IC50 values of 0.06 μM and 0.25 μM, respectively, compared to aspirin's IC50 values of 0.35 μM and 2.4 μM.
Uses
Used in Pharmaceutical Industry:
N-acetyl-2-carboxy Benzenesulfonamide is used as an anti-inflammatory and analgesic agent due to its ability to inhibit COX enzymes, which are involved in the production of prostaglandins responsible for inflammation and pain.
Used in Research Applications:
In the field of research, N-acetyl-2-carboxy Benzenesulfonamide serves as a valuable tool for studying the role of COX enzymes in various physiological and pathological processes. Its potent inhibitory effects on COX-1 and COX-2 make it useful for investigating the mechanisms of action and potential therapeutic targets for the treatment of inflammation and pain.
Used in Drug Development:
N-acetyl-2-carboxy Benzenesulfonamide's potent inhibition of COX enzymes and its structural similarity to aspirin make it a promising candidate for the development of new drugs with improved efficacy and reduced side effects in the treatment of inflammatory and painful conditions.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 849067-18-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,4,9,0,6 and 7 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 849067-18:
(8*8)+(7*4)+(6*9)+(5*0)+(4*6)+(3*7)+(2*1)+(1*8)=201
201 % 10 = 1
So 849067-18-1 is a valid CAS Registry Number.
849067-18-1Relevant articles and documents
Design, synthesis, and biological evaluation of N-acetyl-2- carboxybenzenesulfonamides: A novel class of cyclooxygenase-2 (COX-2) inhibitors
Chen, Qiao-Hong,Rao, P. N. Praveen,Knaus, Edward E.
, p. 2459 - 2468 (2007/10/03)
N-Acetyl-2-carboxybenzenesulfonamide (11), and a group of analogues possessing an appropriately substituted-phenyl substituent (4-F, 2,4-F 2, 4-SO2Me, 4-OCHMe2) attached to its C-4, or C-5 position, were synthesized for ev
