Sodium nifursyrenate [beta-(5-nitro-2-furyl)-p-carboxystyrene
sodium salt,
NSA-Na] is an antibacterial nitrofuran which has been widely used for prevention and treatment of
bacterial infections in fish in Japan. When
NSA-Na was anaerobically incubated with rabbit liver cytosol and
2-hydroxypyrimidine, 1-(p-carboxyphenyl)-5-cyano-3-oxo-1,4-pentadiene (cyano-pentadienone), 1-(p-carboxyphenyl)-5-cyano-3-oxo-1-pentanone (cyano-pentanone), and 1-(p-carboxyphenyl)-5-cyano-3-pentanone (cyano-pentanone) were isolated and identified as the metabolites of the nitrofuran. In addition, when cyano-
pentenone and cyano-pentanone were aerobically incubated with the liver preparation and
NADPH, 1-(p-carboxyphenyl)-5-cyano-3-hydroxy-1-pentene (cyano-pentenol) and 1-(p-carboxyphenyl)-5-cyano-3-pentanol (cyano-pentanol) were also isolated and identified as the metabolites of the nitrofuran in its further metabolism, respectively. The anaerobic incubation of
NSA-Na with rat liver cytosol and
2-hydroxypyrimidine resulted in the formation of cyano-pentadienone and cyano-pentanone. In this case, however, cyano-
pentenone was not detectable. On the other hand, when
NSA-Na was anaerobically incubated with sea bream liver cytosol and
NADPH, the formation of cyano-
pentenone, cyano-pentanone, and cyanopentenol, but not cyano-pentadienone, was observed. Furthermore, cyano-pentanone was metabolized to cyano-pentanol by the fish liver preparation with
NADPH under aerobic conditions. When
NSA-Na was given orally to rabbits, cyano-pentanone, cyano-pentenol, cyano-pentanol, and beta-(acetamido-2-furyl)-p-carboxystyrene (acetamidofuran) were identified as the urinary metabolites of the nitrofuran.(ABSTRACT TRUNCATED AT 250 WORDS)