533925-45-0

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 2-(4-morpholinyl)-2-oxoethyl ester
• CAS NO: 533925-45-0
• Molecular Formula: C19H18F3N3O4
• Molecular Weight: 409.365
• Mol File: 533925-45-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 2-(4-morpholinyl)-2-oxoethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 2-(4-morpholinyl)-2-oxoethyl ester(533925-45-0)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 2-(4-morpholinyl)-2-oxoethyl ester(533925-45-0)

Safety Data

• Hazardous Substances Data: 533925-45-0(Hazardous Substances Data)

Upstream product

• 1440-61-5 N-chloroacetylmorpholine 
• 4394-00-7 Niflumic Acid 

Downstream Products

• 110-91-8 morpholine 
• 51068-78-1 2-hydroxy-1-(morpholin-4-yl)ethan-1-one 
• 4394-00-7 Niflumic Acid 

Relevant articles and documents

Stability studies of some glycolamide ester prodrugs of niflumic acid in aqueous buffers and human plasma by HPLC with UV detection

Glycolamide esters (compounds 1-17) of 2-(3-trifluoromethyl-phenylamino) nicotinic acid (niflumic acid, CAS 4394-00-7) have been synthesized and evaluated as possible prodrugs. In-vitro hydrolysis studies were conducted at selected pH values (1.2, 3.5, 4.8, 7.4 and 7.8) and in human plasma at 37 ± 0.5 °C using HPLC with UV detection. The aqueous (pH 7.4 and 7.8) and enzymatic rates of hydrolysis were substantially affected by the nature of promoieties in this series. The compounds showed good chemical stability in the buffers of low pH values (1.2, 3.5 and 4.8) and appreciable hydrolysis under alkaline conditions and in human plasma. They exhibited long hydrolytic half-lives of 7-46 h in aqueous buffer solutions (pH 7.4 and 7.8) and 14-21 min in human plasma, respectively. It was observed that N,N-disubstituted and cyclic glycolamide derivatives showed 2 fold more hydrolysis in the alkaline pH than monosubstituted derivatives, whereas the piperidino and thiomorpholino derivatives did not undergo chemical hydrolysis. The compounds contain two possible sites for hydrolysis with an increased hydrolytic susceptibility at the terminal aliphatic carbonyl site in aqueous buffers and human plasma solutions. They were found to be cleaved at two hydrolytic carbonyls, namely the nicotinyl (2-5% in enzymatic hydrolysis) and the aliphatic site (7-55% and 70-85% in buffer and plasma hydrolysis, respectively) as revealed by HPLC analysis. The glycolamide ester prodrugs of niflumic acid underwent chemical and enzymatic hydrolysis to release mainly the metabolite 2- (3-trifluoromethyl-phenylamino) nicotinic acid carboxymethyl ester (III) and not the parent drug 2-(3-trifluoromethyl-phenylamino) nicotinic acid. The structure of the metabolite was confirmed by liquid chromatography-mass spectroscopy (LCMS). ECV · Editio Cantor Verlag.