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Chemical Compound Review

dipyrone     sodium[(1,5-dimethyl-3-oxo-2- phenyl...

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Disease relevance of KBioSS_002161

  • The multiplicity of the hepatic tumors was also significantly increased in groups I-a, I-b, and II-a. Hepatic adenoma incidence was related to the dose of dipyrone in the males [1].
  • Elevated odds ratios were observed for MLL+ve (but not MLL-ve) leukemias (2.31 for DNA-damaging drugs, P = 0.03; 5.84 for dipyrone, P = 0.001; and 9.68 for mosquitocidals, P = 0.003) [2].
  • Dipyrone, used in many parts of the world, but not in the United States, is an effective agent; however, it has been implicated in producing agranulocytosis and anaphylactic shock [3].
  • Impairment of the metabolism of dipyrone in asymptomatic carriers of the hepatitis B virus [4].
  • In contrast, combined treatment of hypothermia followed by dipyrone markedly diminished neuronal damage by more than 50% at both 7 days and 2 months of recovery [5].

Psychiatry related information on KBioSS_002161

  • At a dose of 300 mg/kg i.p., dipyrone blocked the maximal hind limb extension in the electroshock model in Wistar rats, the tonic-clonic component of acute sound-induced seizures and the limbic component of audiogenic kindling in genetically susceptible Wistar-derived rats, all in 100% of the animals [6].
  • Locomotor activity was slightly depressed by 300 mg/kg dipyrone [7].
  • Both flunixin and dipyrone produced a small but statistically significant rise in pain thresholds (18% and 21% of maximum possible effect respectively) in the healthy sheep which peaked at 30 min and had returned to pre-drug values by 2-3 h [8].

High impact information on KBioSS_002161

  • The final step in the direct restoration of the nociceptor threshold by peripheral administration of morphine and dipyrone was recently suggested to result from the opening of ATP-sensitive K(+) channels (K(ATP)(+)) [9].
  • The mean levels of transaminases and bilirubin in the paracetamol-treated patients were significantly higher than those found in the dipyrone-treated patients [92 +/- 86 vs. 42 +/- 49 IU (p less than 0.02) for AST and 12 +/- 6.0 vs. 7.0 +/- 2.0 mumoles per liter (p less than 0.01) for bilirubin] [10].
  • These results are consistent with the hypothesis that dipyrone acts in the central nervous system by inhibition of particular prostanoids [11].
  • METHODS: We assessed the effects of pretreatment with acyclovir on bronchoconstriction precipitated by inhalation of sulpyrine in 16 adult patients with mild or moderate aspirin-induced asthma; those who were in stable clinical condition and were hyperresponsive to the sulpyrine provocation test were allocated to this study [12].
  • Thirty minutes after dipyrone intake cerebrospinal fluid thromboxane B2 levels already tended to be lower than those seen in patients with neurologic diseases who were not receiving dipyrone [11].

Chemical compound and disease context of KBioSS_002161


Biological context of KBioSS_002161


Anatomical context of KBioSS_002161


Associations of KBioSS_002161 with other chemical compounds


Gene context of KBioSS_002161


Analytical, diagnostic and therapeutic context of KBioSS_002161

  • METHODS: A single 1.0 gm oral dose of dipyrone was given to consenting patients undergoing elective diagnostic lumbar puncture 0.5, 1, 1.5, 2, 4, 6, 8, or 12 hours before the tap [11].
  • Using high-performance liquid chromatography (HPLC), we measured concentrations of dipyrone in the serum of patients who had received the drug and observed a negative correlation between the concentrations of dipyrone in the blood and the percentage of each analyte concentration [31].
  • Microinjection of cholecystokinin (1 ng/0.5 microl) into PAG blocked the antinociceptive effect of a subsequent microinjection of dipyrone (150 microg/0.5 microl) into the same site, as evaluated by the tail flick and hot plate tests [21].
  • (ii) Effect of dipyrone A and dipyrone B on induction of DEN-initiated GST-P+ hepatic foci in a medium-term bioassay system: 0.4% dipyrone A in drinking water and 0.57% dipyrone A or dipyrone B in powdered diet after DEN initiation had similar enhancing effects on the development of GST-P+ foci (P less than 0.001) [32].
  • OBJECTIVE: To conduct a randomized, placebo controlled, double blind study to assess the effect of dipyrone on the pain and symptoms associated with migraine without aura or with aura and the adverse effect profile of this medication [33].


  1. Carcinogenicity of dipyrone in (C57BL/6 X C3H)F1 mice. Kumagai, H., Kawaura, A., Shibata, M., Otsuka, H. J. Natl. Cancer Inst. (1983) [Pubmed]
  2. Transplacental chemical exposure and risk of infant leukemia with MLL gene fusion. Alexander, F.E., Patheal, S.L., Biondi, A., Brandalise, S., Cabrera, M.E., Chan, L.C., Chen, Z., Cimino, G., Cordoba, J.C., Gu, L.J., Hussein, H., Ishii, E., Kamel, A.M., Labra, S., Magalhães, I.Q., Mizutani, S., Petridou, E., de Oliveira, M.P., Yuen, P., Wiemels, J.L., Greaves, M.F. Cancer Res. (2001) [Pubmed]
  3. Use of antipyretic analgesics in the pediatric patient. Gladtke, E. Am. J. Med. (1983) [Pubmed]
  4. Impairment of the metabolism of dipyrone in asymptomatic carriers of the hepatitis B virus. Levy, M., Leibowich, I., Zylber-Katz, E., Ilan, Y., Granit, L., Sviri, S., Caraco, Y. Clin. Pharmacol. Ther. (1997) [Pubmed]
  5. Long-lasting neuroprotective effect of postischemic hypothermia and treatment with an anti-inflammatory/antipyretic drug. Evidence for chronic encephalopathic processes following ischemia. Coimbra, C., Drake, M., Boris-Möller, F., Wieloch, T. Stroke (1996) [Pubmed]
  6. Dipyrone, a novel anticonvulsant agent? Insights from three experimental epilepsy models. Doretto, M.C., Garcia-Cairasco, N., Pimenta, N.J., Souza, D.A., Tatsuo, M.A. Neuroreport (1998) [Pubmed]
  7. Options for management of acute pain in the rat. Abbott, F.V., Bonder, M. Vet. Rec. (1997) [Pubmed]
  8. The effects of opioid and alpha 2 adrenergic blockade on non-steroidal anti-inflammatory drug analgesia in sheep. Chambers, J.P., Waterman, A.E., Livingston, A. J. Vet. Pharmacol. Ther. (1995) [Pubmed]
  9. Peripheral analgesic blockade of hypernociception: activation of arginine/NO/cGMP/protein kinase G/ATP-sensitive K+ channel pathway. Sachs, D., Cunha, F.Q., Ferreira, S.H. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  10. Hepatitis during measles in young adults: possible role of antipyretic drugs. Ackerman, Z., Flugelman, M.Y., Wax, Y., Shouval, D., Levy, M. Hepatology (1989) [Pubmed]
  11. Cerebrospinal fluid prostaglandins after systemic dipyrone intake. Levy, M., Brune, K., Zylber-Katz, E., Cohen, O., Caraco, Y., Geisslinger, G. Clin. Pharmacol. Ther. (1998) [Pubmed]
  12. Effect of acyclovir on bronchoconstriction and urinary leukotriene E4 excretion in aspirin-induced asthma. Yoshida, S., Sakamoto, H., Yamawaki, Y., Shoji, T., Akahori, K., Onuma, K., Nakagawa, H., Hasegawa, H., Amayasu, H. J. Allergy Clin. Immunol. (1998) [Pubmed]
  13. Comparison of intravenous acetylsalicylic acid and dipyrone in postoperative pain: an interim report. Blendinger, I., Eberlein, H.J. British journal of clinical pharmacology. (1980) [Pubmed]
  14. Effect of dexamethasone and dipyrone on lingual and inferior alveolar nerve hypersensitivity following third molar extractions: preliminary report. Barron, R.P., Benoliel, R., Zeltser, R., Eliav, E., Nahlieli, O., Gracely, R.H. Journal of orofacial pain. (2004) [Pubmed]
  15. Mutagenicity of reaction products of sulpyrine with nitrite. Sakai, A., Yoshikawa, K., Tanimura, A., Tomita, I. Mutat. Res. (1981) [Pubmed]
  16. Diclofenac versus dipyrone in acute renal colic: a double-blind controlled trial. Miralles, R., Camí, J., Gutiérrez, J., Torné, J., Garcés, J.M., Badenas, J.M. Eur. J. Clin. Pharmacol. (1987) [Pubmed]
  17. Inhibition of analgesic-induced asthma by leukotriene receptor antagonist ONO-1078. Yamamoto, H., Nagata, M., Kuramitsu, K., Tabe, K., Kiuchi, H., Sakamoto, Y., Yamamoto, K., Dohi, Y. Am. J. Respir. Crit. Care Med. (1994) [Pubmed]
  18. Clinical pharmacokinetics of dipyrone and its metabolites. Levy, M., Zylber-Katz, E., Rosenkranz, B. Clinical pharmacokinetics. (1995) [Pubmed]
  19. Inhibition of ADP-induced platelet aggregation by dipyrone in patients with acute myocardial infarction. Weinberger, I., Joshua, H., Friedmann, J., Rahamim, S., Agmon, J. Thromb. Haemost. (1979) [Pubmed]
  20. A Population-Based Case-Control Teratologic Study of Oral Dipyrone Treatment during Pregnancy. B??nhidy, F., Acs, N., Puh??, E., Czeizel, A.E. Drug safety : an international journal of medical toxicology and drug experience (2007) [Pubmed]
  21. Involvement of cholecystokinin in the opioid tolerance induced by dipyrone (metamizol) microinjections into the periaqueductal gray matter of rats. Tortorici, V., Nogueira, L., Aponte, Y., Vanegas, H. Pain (2004) [Pubmed]
  22. Effects of dipyrone on prostaglandin production by human platelets and cultured bovine aortic endothelial cells. Eldor, A., Polliack, G., Vlodavsky, I., Levy, M. Thromb. Haemost. (1983) [Pubmed]
  23. Anti-inflammatory effect of roxithromycin in patients with aspirin-intolerant asthma. Shoji, T., Yoshida, S., Sakamoto, H., Hasegawa, H., Nakagawa, H., Amayasu, H. Clin. Exp. Allergy (1999) [Pubmed]
  24. The antinociceptive effect of PAG-microinjected dipyrone in rats is mediated by endogenous opioids of the rostral ventromedical medulla. Vasquez, E., Vanegas, H. Brain Res. (2000) [Pubmed]
  25. Dipyrone (metamizole) metabolites interfere with HPLC analysis of plasma catecholamines but not with the determination of urinary catecholamines. Müssig, K., Pfäfflin, A., Häring, H.U., Schleicher, E.D. Clin. Chem. (2006) [Pubmed]
  26. Pyrazolone derivatives. Brogden, R.N. Drugs (1986) [Pubmed]
  27. The effects on platelet aggregation and prostanoid biosynthesis of two parenteral analgesics: ketorolac tromethamine and dipyrone. Geisslinger, G., Peskar, B.A., Pallapies, D., Sittl, R., Levy, M., Brune, K. Thromb. Haemost. (1996) [Pubmed]
  28. Variants of cyclooxygenase-1 and their roles in medicine. Simmons, D.L. Thromb. Res. (2003) [Pubmed]
  29. Does dipyrone have any effect on respiratory function in COPD patients? Gulmez, S.E., Tulunay, F.C., Beder, S., Kayacan, O., Karnak, D. Respiratory medicine. (2006) [Pubmed]
  30. Mediators involved in the febrile response induced by Tityus serrulatus scorpion venom in rats. Pessini, A.C., Santos, D.R., Arantes, E.C., Souza, G.E. Toxicon (2006) [Pubmed]
  31. Dipyrone interference on several common biochemical tests. Gascón, N., Otal, C., Martínez-Brú, C., Mercé, J., Cortés, M., Arcelus, R., Queraltó, J.M., Sánchez, J.M., González-Sastre, F. Clin. Chem. (1993) [Pubmed]
  32. Tumor promoting potential in male F344 rats and mutagenicity in Salmonella typhimurium of dipyrone. Izumi, K., Sano, N., Otsuka, H., Kinouchi, T., Ohnishi, Y. Carcinogenesis (1991) [Pubmed]
  33. Intravenous dipyrone in the acute treatment of migraine without aura and migraine with aura: a randomized, double blind, placebo controlled study. Bigal, M.E., Bordini, C.A., Tepper, S.J., Speciali, J.G. Headache. (2002) [Pubmed]
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