261766-32-9 Usage
Description
N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE is an aromatic amide derivative of indomethacin, a nonsteroidal anti-inflammatory drug (NSAID). It is characterized by its potent and selective reversible inhibition of cyclooxygenase-2 (COX-2), an enzyme involved in the production of prostaglandins, which are associated with inflammation and pain.
Uses
Used in Pharmaceutical Industry:
N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE is used as an anti-inflammatory agent for its potent and selective reversible inhibition of COX-2. This makes it a potential candidate for the development of new drugs targeting inflammation and pain relief, with potentially fewer side effects compared to traditional NSAIDs.
Used in Research Applications:
In the field of medical research, N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE serves as a valuable tool for studying the role of COX-2 in various physiological and pathological processes. Its potent and selective inhibition of COX-2 can help researchers better understand the enzyme's function and its contribution to inflammation, pain, and other related conditions.
Used in Drug Development:
N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE is used as a lead compound in the development of new drugs with improved efficacy and safety profiles. Its potent and selective COX-2 inhibition makes it an attractive starting point for the design of novel therapeutic agents that may offer better pain relief and reduced side effects compared to existing NSAIDs.
Biological Activity
n-(2-phenylethyl)-indomethacin amide is a reversible, potent and selective cox-2 inhibitor [1].cyclooxygenase (cox) is an enzyme responsible for formation of prostanoids, including thromboxane and prostaglandins such as prostacyclin. cox-1 is the constitutive isoform and is mainly responsible for the synthesis of cytoprotective prostaglandins in the gastrointestinal tract (gi) and of the proaggregatory thromboxane in blood platelets. cox-2 is inducible and short-lived that is stimulated by endotoxin, cytokines, and mitogens. cox-2 plays important roles in prostaglandin biosynthesis in inflammatory cells the central nervous system [1].n-(2-phenylethyl)-indomethacin amide (n-2pia) is a reversible, potent and selective cox-2 inhibitor that inhibits human recombinant cox-2 and ovine cox-1 with ic50 values of 0.06 and >66 μm, respectively. it is over 1000 times less potent as an inhibitor of ovine cox-1. n-(2-phenylethyl)-indomethacin amide is an analogous derivative of indomethacin that shows selective against cox-2 [1].in the carageenan-induced foot pad edema assay, orally administration of n-2pia showed anti-inflammatory activity [1].
Check Digit Verification of cas no
The CAS Registry Mumber 261766-32-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,6,1,7,6 and 6 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 261766-32:
(8*2)+(7*6)+(6*1)+(5*7)+(4*6)+(3*6)+(2*3)+(1*2)=149
149 % 10 = 9
So 261766-32-9 is a valid CAS Registry Number.
261766-32-9Relevant articles and documents
Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors
Kalgutkar, Amit S.,Marnett, Alan B.,Crews, Brenda C.,Remmel, Rory P.,Marnett, Lawrence J.
, p. 2860 - 2870 (2007/10/03)
Recent studies from our laboratory have shown that derivatization of the carboxylate moiety in substrate analogue inhibitors, such as 5,8,11,14- eicosatetraynoic acid, and in nonsteroidal antiinflammatory drugs (NSAIDs), such as indomethacin and meclofenamic acid, results in the generation of potent and selective cyclooxygenase-2 (COX-2) inhibitors (Kalgutkar et al. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 925-930). This paper summarizes details of the structure-activity studies involved in the transformation of the arylacetic acid NSAID, indomethacin, into a COX-2-selective inhibitor. Many of the structurally diverse indomethacin esters and amides inhibited purified human COX-2 with IC50 values in the low-nanomolar range but did not inhibit ovine COX-1 activity at concentrations as high as 66 μM. Primary and secondary amide analogues of indomethacin were more potent as COX-2 inhibitors than the corresponding tertiary amides. Replacement of the 4- chlorobenzoyl group in indomethacin esters or amides with the 4-bromobenzyl functionality or hydrogen afforded inactive compounds. Likewise, exchanging the 2-methyl group on the indole ring in the ester and amide series with a hydrogen also generated inactive compounds. Inhibition kinetics revealed that indomethacin amides behave as slow, tight-binding inhibitors of COX-2 and that selectivity is a function of the time-dependent step. Conversion of indomethacin into ester and amide derivatives provides a facile strategy for generating highly selective COX-2 inhibitors and eliminating the gastrointestinal side effects of the parent compound.
