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Metabolism of sodium nifurstyrenate, a veterinary antimicrobial nitrofuran, in animals and fish.

Abstract
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)
AuthorsK Tatsumi, S Kitamura, M Kato, K Hiraoka
JournalDrug metabolism and disposition: the biological fate of chemicals (Drug Metab Dispos) 1992 Mar-Apr Vol. 20 Issue 2 Pg. 226-33 ISSN: 0090-9556 [Print] United States
PMID1352214 (Publication Type: Journal Article)
Chemical References
  • Nitrofurans
  • Nitrosamines
  • Styrenes
  • NAD
  • nifurstyrenic acid
  • N-nitrosoallyl-2,3-dihydroxypropylamine
Topics
  • Animals
  • Cricetinae
  • Cytosol (metabolism)
  • Fishes
  • Guinea Pigs
  • Liver (metabolism)
  • Male
  • Mesocricetus
  • Mice
  • Mutagenicity Tests
  • NAD (metabolism)
  • Nitrofurans (metabolism, toxicity)
  • Nitrosamines (metabolism)
  • Rabbits
  • Rats
  • Rats, Inbred Strains
  • Styrenes (metabolism, toxicity)

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