92440-76-1

Usage

Uses

Degradation product/impurity of trimethoprim (T795615).

InChI:InChI=1/C14H17N3O4/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-16-14(15)17-13(9)18/h5-7H,4H2,1-3H3,(H3,15,16,17,18)

Upstream product

• 738-70-5 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine 
• 70311-20-5 3-(3,4,5-trimethoxyphenyl)propionic acid ethyl ester 
• 593-85-1 diguanidine carbonate 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 92653-78-6 2-amino-4-methylamino-5-(3,4,5-trimethoxybenzyl)pyrimidine 
• 55694-04-7 2-amino-4-chloro-5-(3,4,5-trimethoxybenzyl)pyrimidine 

Relevant academic research and scientific papers

Separation, analyses and syntheses of trimethoprim impurities

The analysis of several impurities of the chemotherapeutic agent trimethoprim with various methods, including thin layer chromatography, gas chromatography, capillary electrophoresis as well as nuclear magnetic resonance is described. These methods were used to identify new impurities in trimethoprim batches. The main impurities were separated by column chromatography. To ensure the identity of the impurities, de novo syntheses were successfully carried out. With the methods described, it was possible to detect, separate and identify new impurities in trimethoprim batches.

Kinetics and pH profile of thermal decomposition of trimethoprim in aqueous solution

The thermal decomposition of trimethoprim, effected by stringent conditions in aqueous solution, has been studied kinetically to elucidate the mechanism of decomposition and to determine stability related properties such as shelf life, acid dissociation constants and activation parameters. The k/pH profiles based on experimentally measured, theoretically calculated and computer predicted rate constants confirm that trimethoprim decomposes along three concomitant pathways associated with the three pH-related drug species existing in aqueous solution.

Degradation of trimethoprim

Trimethoprim undergoes thermally and photochemically catalyzed hydrolysis or oxidation to give rise to at least five products. The structures of these compounds were determined by physical methods and it was found that the resonance of C-5 in the 13C NMR spectrum is indicative of the substitution pattern of the resultant amino hydroxy pyrimidines.