Naunyn-Schmiedeberg's Archives of Pharmacology

, Volume 309, Issue 2, pp 203–205 | Cite as

4,4′-Dihydroxyphenazone as an urinary metabolite of phenazone in different species including man

  • H. Bässmann
  • J. Böttcher
  • R. Schüppel


4,4′-Dihydroxyphenazone (4-hydroxy-1-(4′-hydroxyphenyl)-2,3-dimethyl-3-pyrazoline-5-one) was isolated as a metabolite of phenazone (antipyrine) after acid hydrolysis of rat urine. This was characterized and identified by NMR, MS, IR, UV, Fp and ε270. After dosage with phenazone, 4,4′-dihydroxyphenazone is excreted in conjugated form by man, rabbit, guinea pig and rat. In the rat it is further shown, that conjugates of 4,4′-dihydroxyphenazone are formed by glucuronidation as well as by sulfatation. The metabolite seems to add substantially to the overall metabolic pattern of phenazone in these species.

Key words

Phenazone/antipyrine Biotransformation Drug hydroxylation Secondary metabolites 


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Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • H. Bässmann
    • 1
  • J. Böttcher
    • 1
  • R. Schüppel
    • 1
  1. 1.Institut für Pharmakologie und ToxikologieTechnische Universität BraunschweigBraunschweigFederal Republic of Germany

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