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Chemical Compound Review

Clorizol     5-amino-4-chloro-2-phenyl- pyridazin-3-one

Synonyms: Curbetan, Pyrazone, Pyrazonl, PYRAZON, Phenosane, ...
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Disease relevance of Phenazone


High impact information on Phenazone

  • Whereas the elimination half-life did not change, clearance of phenazone decreased by about 50% with age in healthy women receiving phenazone without theophylline [4].
  • Human over-use of analgesics containing phenacetin, antipyrene (phenazone) and caffeine has been associated with the development of both renal pelvic and bladder tumors [5].
  • Compared with placebo, the phenazone treatment also resulted in a significant improvement in the associated migraine symptoms of nausea, phonophobia and photophobia [3].
  • Abuse of combination analgesics containing phenacetin, phenazone and caffeine may be a risk factor for development of ureteral tumors [6].
  • Thus, the two metabolites 1,5-di-methyl-1,2-dehydro-3-pyrazolone (DP) and 4-(2-methylethyl)-1,5-dimethyl-1,2-dehydro-3-pyrazolone (PDP), postulated for the degradation of phenazone and propyphenazone, were identified and detected up to the microg/L level in raw and drinking water samples from public water supply [7].

Chemical compound and disease context of Phenazone


Biological context of Phenazone


Anatomical context of Phenazone


Associations of Phenazone with other chemical compounds


Gene context of Phenazone

  • The results of the study suggest that the depression in phenazone elimination in lead intoxication is possibly due to depressed hepatic cytochrome P450 levels [21].
  • Photochemical decomposition of phenazone derivatives. Part 7: Mechanism of decomposition in aqueous solutions [22].

Analytical, diagnostic and therapeutic context of Phenazone


  1. Prophylaxis of neonatal jaundice with maternal antipyrine treatment. Lewis, P.J., Friedman, L.A. Lancet (1979) [Pubmed]
  2. Quantifying hepatic function in the presence of liver disease with phenazone (antipyrine) and its metabolites. St Peter, J.V., Awni, W.M. Clinical pharmacokinetics. (1991) [Pubmed]
  3. Efficacy of phenazone in the treatment of acute migraine attacks: a double-blind, placebo-controlled, randomized study. Göbel, H., Heinze, A., Niederberger, U., Witt, T., Zumbroich, V. Cephalalgia : an international journal of headache. (2004) [Pubmed]
  4. The relationship between phenazone (antipyrine) metabolite formation and theophylline metabolism in healthy and frail elderly women. Groen, K., Horan, M.A., Roberts, N.A., Gulati, R.S., Miljkovic, B., Jansen, E.J., Paramsothy, V., Breimer, D.D., van Bezooijen, C.F. Clinical pharmacokinetics. (1993) [Pubmed]
  5. The influence of antipyrene on N-[4-(5-nitro-2-furyl)-2-thiazolyl]-formamide-induced urinary tract carcinogenesis. Johansson, S.L., Anderström, C. Carcinogenesis (1988) [Pubmed]
  6. Carcinoma of the ureter: a clinicopathologic study of 49 cases. Anderström, C., Johansson, S.L., Pettersson, S., Wahlqvist, L. J. Urol. (1989) [Pubmed]
  7. Detection and identification of phenazone-type drugs and their microbial metabolites in ground and drinking water applying solid-phase extraction and gas chromatography with mass spectrometric detection. Zühlke, S., Dünnbier, U., Heberer, T. Journal of chromatography. A. (2004) [Pubmed]
  8. Rhabdomyolysis after suicidal ingestion of an overdose of caffeine, acetaminophen and phenazone as a fixed-dose combination (Spalt N). Michaelis, H.C., Sharifi, S., Schoel, G. J. Toxicol. Clin. Toxicol. (1991) [Pubmed]
  9. Pharmacokinetics of phenazone (antipyrine) in rabbits with experimental common bile duct obstruction. Wójcicki, J., Sulikowski, T., Wójcicki, M., Droździk, M., Gawrońska-Szklarz, B., Barcew-Wiszniewska, B., Skowron, J., Rózewicka, L. Br. J. Pharmacol. (1996) [Pubmed]
  10. Phenazone as a marker of liver-metabolic function in patients with acute leukemia. Wiela-Hojenska, A., Orzechowska-Juzwenko, K., Usnarska-Zubkiewicz, L., Kotlarek-Haus, S., Hurkacz, M. International journal of clinical pharmacology and therapeutics. (1999) [Pubmed]
  11. Effects of chronic treatment with phenazone on the hot-plate test and [3H]serotonin binding sites in pons and cortex membranes of the rat. Sandrini, M., Vitale, G., Pini, L.A., Sternieri, E., Bertolini, A. Pharmacology (1993) [Pubmed]
  12. Haem biosynthesis and hydroxylation of phenazone during lead intoxication. Campbell, B.C., Meredith, P.A., Moore, M.R., Brodie, M.J., Thompson, G.G., Goldberg, A. Biochem. Soc. Trans. (1976) [Pubmed]
  13. Effect of chloridazone on the animal organism. Mlynarcíková, H., Legáth, J., Guzy, J., Kovalkovicová, N., Ivanko, S. Gen. Physiol. Biophys. (1999) [Pubmed]
  14. Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Brune, K., Neubert, A. Clinical and experimental rheumatology. (2001) [Pubmed]
  15. The organochlorine herbicide chloridazon interacts with cell membranes. Suwalsky, M., Benites, M., Villena, F., Norris, B., Quevedo, L. Comp. Biochem. Physiol. C, Pharmacol. Toxicol. Endocrinol. (1998) [Pubmed]
  16. Cytogenetic effects of the herbicide chloridazon in cultured sheep lymphocytes. Siviková, K., Dianovský, J. Acta Vet. Hung. (1997) [Pubmed]
  17. 4,4'-Dihydroxyphenazone as an urinary metabolite of phenazone in different species including man. Bässmann, H., Böttcher, J., Schüppel, R. Naunyn Schmiedebergs Arch. Pharmacol. (1979) [Pubmed]
  18. Comparative pharmacokinetics of antipyrine (phenazone) in the baboon, cynomolgus monkey and rhesus monkey. Doyle, E., Chasseaud, L.F. Toxicology (1981) [Pubmed]
  19. Individual and combined effect of anthracene, cadmium, and chloridazone on growth and activity of SOD izoformes in three Scenedesmus species. Zbigniew, T., Wojciech, P. Ecotoxicol. Environ. Saf. (2006) [Pubmed]
  20. Phenazone versus placebo: effects on post-operative course. Skjelbred, P., Løkken, P. Eur. J. Clin. Pharmacol. (1980) [Pubmed]
  21. The effects of industrial lead poisoning on cytochrome P450 mediated phenazone (antipyrine) hydroxylation. Meredith, P.A., Campbell, B.C., Moore, M.R., Goldberg, A. Eur. J. Clin. Pharmacol. (1977) [Pubmed]
  22. Photochemical decomposition of phenazone derivatives. Part 7: Mechanism of decomposition in aqueous solutions. Marciniec, B. Die Pharmazie. (1985) [Pubmed]
  23. Regional jejunal perfusion, a new in vivo approach to study oral drug absorption in man. Lennernäs, H., Ahrenstedt, O., Hällgren, R., Knutson, L., Ryde, M., Paalzow, L.K. Pharm. Res. (1992) [Pubmed]
  24. Metabolic functions of the liver during chemotherapy in children with acute lymphoblastic leukemia. Wiela-Hojenska, A., Gorczynska, E., Orzechowska-Juzwenko, K., Golebiowski, W., Hurkacz, M., Boguslawska-Jaworska, J. International journal of clinical pharmacology and therapeutics. (2001) [Pubmed]
  25. Influence of bed rest on the pharmacokinetics of phenazone. Elfström, J., Lindgren, S. Eur. J. Clin. Pharmacol. (1978) [Pubmed]
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