261766-32-9

Basic information

• Product Name: N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE
• Synonyms: N-(2-PHENYLETHYL)-1-P-CHLOROBENZOYL-5-METHOXY-2-METHYLINDOLE-3-ACETAMIDE;N-(2-PHENYLETHYL)-1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOLE-3-ACETAMIDE;N-2PIA;N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE;1-(4-Chlorobenzoyl)-5-Methoxy-2-Methyl-N-(2-phenylethyl)-1H-indole-3-acetaMide
• CAS NO: 261766-32-9
• Molecular Formula: C₂₇H₂₅ClN₂O₃
• Molecular Weight: 460.95
• Product Categories: Inhibitors;Cyclooxygenase (COX) Enzymes;Cyclooxygenase Inhibitors;CyclooxygenaseCell Signaling Enzymes;CyclooxygenaseEnzyme Inhibitors by Enzyme;A to;Arachidonic Acid Cascade;Enzyme Inhibitors
• Mol File: 261766-32-9.mol

Chemical Properties

• Boiling Point: 640.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: ≤80mg/ml in ethanol;10mg/ml in DMSO;14mg/ml in dimethyl formamide
• PKA: 15.12±0.46(Predicted)
• CAS DataBase Reference: N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE(261766-32-9)
• EPA Substance Registry System: N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE(261766-32-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 261766-32-9(Hazardous Substances Data)

Usage

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].

Upstream product

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 64-04-0 phenethylamine 

Downstream Products

• 288854-10-4 5-methoxy-2-methylindole-3-phenethylacetamide 

Relevant articles and documents

Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors

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.