Summary
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 ε 270. 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.
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This work was supported by the Deutsche Forschungsgemeinschaft
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Bässmann, H., Böttcher, J. & Schüppel, R. 4,4′-Dihydroxyphenazone as an urinary metabolite of phenazone in different species including man. Naunyn-Schmiedeberg's Arch. Pharmacol. 309, 203–205 (1979). https://doi.org/10.1007/BF00501230
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DOI: https://doi.org/10.1007/BF00501230