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Metamizole, or dipyrone (DIP), is a widely used prodrug (bioprecursor class) with powerful analgesic and antipyretic effects. In the gastrointestinal tract DIP is first hydrolyzed to 4-methylaminoantipirine (4MAA), which is then absorbed and metabolized in the liver to the corresponding 4-aminoantipyrine (4AA) and 4-formylamino-antipyrine (4-FAA) derivatives. Furthermore, the 4-AA suffers an acylation reaction to afford the 4acetylaminoantipyrine (4-AAA)1. Despite some authors have proposed that 4-MAA and 4-AA are the active metabolites of dipyrone2, the exact mechanism of action of these and other bioactive metabolites is still unknown. Thus, in this work we have synthesized the main metabolites of dipyrone3 and these have been used in studies4 that aims to compare their antipyretic effects in the fever induced by LPS and Tsv (Tityus serrulatus venom)5.

Synthesis of Dipyrone Metabolites and Evaluation of their Antipyretic Effect