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Chemical Compound Review

Dipyrine     4-dimethylamino-1,5-dimethyl- 2-phenyl...

Synonyms: Eufibron, Amidophen, Pyramidone, AMINOPYRINE, Amidazophen, ...
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Disease relevance of aminophenazone


Psychiatry related information on aminophenazone


High impact information on aminophenazone


Chemical compound and disease context of aminophenazone


Biological context of aminophenazone


Anatomical context of aminophenazone

  • The mean aminopyrine clearance per individual hepatocyte showed no significant difference between cirrhotic and noncirrhotic patients (3.52 +/- 1.60 x 10(-10) mL/min vs. 3.65 +/- 1.50 x 10(-10) mL/min, respectively; P greater than 0.10) [18].
  • Impairment of aminopyrine clearance in aspirin-damaged canine gastric mucosa [22].
  • The ratio of aminopyrine concentration in the gastric juice and blood plasma was not significantly changed by GH-RIH, indicating that the reduction in mucosal blood flow was secondary to an inhibition of gastric secretion [23].
  • Under substrate-depleted conditions, the oxygen consumption and the aminopyrine accumulation of fundic mucosa were not significantly increased by histamine [17].
  • These findings indicate that movement of aminopyrine from plasma to gastric lumen is impaired in damaged epithelium, making the aminopyrine clearance technique an unreliable method to accurately measure absolute gastric blood flow in this experimental setting [22].

Associations of aminophenazone with other chemical compounds


Gene context of aminophenazone

  • The activities of the CYP2C19(H99I) mutant and the chimeras that replaced residues 228-340 were lower than those for CYP2C19 toward S-mephenytoin, aminopyrine, and testosterone [28].
  • 3. Human steroidogenic CYP17 also catalysed aminopyrine N-demethylation and the activity was comparable with that for CYP3A4 which is a dominant P450 in human liver [29].
  • 2. Among the hepatic P450s, the N-demethylation of aminopyrine was catalysed most efficiently by CYP2C19, followed by CYP2C8, 2D6, 2C18 and 1A2, whereas the activity with CYP2E1 was negligible [29].
  • Bisphenol A (1 mM) most efficiently inhibited aminopyrine N-demethylation by CYP2C8 and CYP2C19 by 82% and 85%, respectively, whereas inhibition of the activities by CYP 2B6 and 2D6 was less than 40% [30].
  • 4. These results suggest that several human hepatic P450s, especially CYP2C19, and steroidogenic CYP17 exhibit aminopyrine N-demethylase activity [29].

Analytical, diagnostic and therapeutic context of aminophenazone


  1. Agranulocytosis caused by Chinese herbal medicines. Dangers of medications containing aminopyrine and phenylbutazone. Ries, C.A., Sahud, M.A. JAMA (1975) [Pubmed]
  2. Abnormal aminopyrine metabolism in patients with hepatic neoplasm. Detection by breath test. Hepner, G.W., Uhlin, S.R., Lipton, A., Harvey, H.A., Rohrer, V. JAMA (1976) [Pubmed]
  3. Effect of strain differences and tumor presence on microsomal drug metabolism in the guinea pig: brief communication. Litterst, C.L., Mimnaugh, E.G., Gram, T.E. J. Natl. Cancer Inst. (1977) [Pubmed]
  4. Aminopyrine N-demethylation by rats with liver cirrhosis. Evidence for the intact cell hypothesis. A morphometric-functional study. Reichen, J., Arts, B., Schafroth, U., Zimmermann, A., Zeltner, B., Zysset, T. Gastroenterology (1987) [Pubmed]
  5. Early diagnosis of alcoholic cirrhosis by the aminopyrine breath test. Saunders, J.B., Lewis, K.O., Paton, A. Gastroenterology (1980) [Pubmed]
  6. Diurnal rhythms of aminopyrine metabolism: failure to sleep deprivation to affect them. Poley, G.E., Shively, C.A., Vesell, E.S. Clin. Pharmacol. Ther. (1978) [Pubmed]
  7. Hepatic aminopyrine N-demethylase system: further studies of assay procedure. Matsubara, T., Touchi, A., Tochino, Y. Jpn. J. Pharmacol. (1977) [Pubmed]
  8. Autoantibody to the gastrin receptor in pernicious anemia. de Aizpurua, H.J., Ungar, B., Toh, B.H. N. Engl. J. Med. (1985) [Pubmed]
  9. Immunoaffinity chromatography of carcinogen DNA adducts with polyclonal antibodies directed against benzo[a]pyrene diol-epoxide-DNA. Tierney, B., Benson, A., Garner, R.C. J. Natl. Cancer Inst. (1986) [Pubmed]
  10. Generation of free radical intermediates from foreign compounds by neutrophil-derived oxidants. Kalyanaraman, B., Sohnle, P.G. J. Clin. Invest. (1985) [Pubmed]
  11. Extracellular calcium and cholinergic stimulation of isolated canine parietal cells. Soll, A.H. J. Clin. Invest. (1981) [Pubmed]
  12. Quantitative assessment of hepatic function by breath analysis after oral administration of (14C)aminopyrine. Hepner, G.W., Vesell, E.S. Ann. Intern. Med. (1975) [Pubmed]
  13. Phenobarbital influences the development of sodium retention in liver disease induced by bile duct ligation in the rat. Wensing, G., Branch, R.A. Hepatology (1990) [Pubmed]
  14. Albumin but not fibrinogen synthesis correlates with galactose elimination capacity in patients with cirrhosis of the liver. Ballmer, P.E., Reichen, J., McNurlan, M.A., Sterchi, A.B., Anderson, S.E., Garlick, P.J. Hepatology (1996) [Pubmed]
  15. Hepatitis C virus antibodies in chronic alcoholic patients: association with severity of liver injury. Parés, A., Barrera, J.M., Caballería, J., Ercilla, G., Bruguera, M., Caballería, L., Castillo, R., Rodés, J. Hepatology (1990) [Pubmed]
  16. Hematologic effects of antipyretic analgesics. Drug-induced agranulocytosis. Heit, W.F. Am. J. Med. (1983) [Pubmed]
  17. Substrate-level energy dependence of acid secretion in the isolated human gastric mucosa. Chacín, J., Prieto, A., Cárdenas, P. Gastroenterology (1985) [Pubmed]
  18. Direct evidence for the intact hepatocyte theory in patients with liver cirrhosis. Kawasaki, S., Imamura, H., Bandai, Y., Sanjo, K., Idezuki, Y. Gastroenterology (1992) [Pubmed]
  19. Effect of portacaval shunt on drug disposition in patients with cirrhosis. Pomier-Layrargues, G., Huet, P.M., Villeneuve, J.P., Marleau, D. Gastroenterology (1986) [Pubmed]
  20. Aspirin induces morphological transformation to the secretory state in isolated rabbit parietal cells. Murthy, U.K., Levine, R.A. Gastroenterology (1991) [Pubmed]
  21. The effects of variation in dietary protein and ethanol on hepatic microsomal drug metabolism in the rat. Mitchell, M.C., Mezey, E., Maddrey, W.C. Hepatology (1981) [Pubmed]
  22. Impairment of aminopyrine clearance in aspirin-damaged canine gastric mucosa. Miller, T.A., Henagan, J.M., Loy, T.M. Gastroenterology (1983) [Pubmed]
  23. Effect of growth hormone release-inhibiting hormone on gastric secretion, mucosal blood flow, and serum gastrin. Konturek, S.J., Tasler, J., Cieszkowski, M., Coy, D.H., Schally, A.V. Gastroenterology (1976) [Pubmed]
  24. Visual event-related P300 potentials in early portosystemic encephalopathy. Kügler, C.F., Lotterer, E., Petter, J., Wensing, G., Taghavy, A., Hahn, E.G., Fleig, W.E. Gastroenterology (1992) [Pubmed]
  25. Effect of ethanol on acid secretion by isolated gastric glands from rabbit. Reichstein, B.J., Okamoto, C., Forte, J.G. Gastroenterology (1986) [Pubmed]
  26. Comparison of gastric mucosal blood flow as determined by aminopyrine clearance and gamma-labeled microspheres. Archibald, L.H., Moody, F.G., Simons, M.A. Gastroenterology (1975) [Pubmed]
  27. Measurement of gastric mucosal blood flow in dogs by the 99mTc-4-methylaminophenazone clearance technique. Döbrönte, Z., Láng, J., Sági, I., Varró, V. Gastroenterology (1982) [Pubmed]
  28. Amino acid residues affecting the activities of human cytochrome P450 2C9 and 2C19. Niwa, T., Kageyama, A., Kishimoto, K., Yabusaki, Y., Ishibashi, F., Katagiri, M. Drug Metab. Dispos. (2002) [Pubmed]
  29. Contribution of human hepatic cytochrome P450s and steroidogenic CYP17 to the N-demethylation of aminopyrine. Niwa, T., Sato, R., Yabusaki, Y., Ishibashi, F., Katagiri, M. Xenobiotica (1999) [Pubmed]
  30. Inhibition of drug-metabolizing enzyme activity in human hepatic cytochrome P450s by bisphenol A. Niwa, T., Tsutsui, M., Kishimoto, K., Yabusaki, Y., Ishibashi, F., Katagiri, M. Biol. Pharm. Bull. (2000) [Pubmed]
  31. Depression of aminopyrine metabolism by influenza vaccination. Kramer, P., McClain, C.J. N. Engl. J. Med. (1981) [Pubmed]
  32. Aminopyrine N-demethylation: a prognostic test of liver function in patients with alcoholic liver disease. Schneider, J.F., Baker, A.L., Haines, N.W., Hatfield, G., Boyer, J.L. Gastroenterology (1980) [Pubmed]
  33. Effects of proximal gastric vagotomy and antrectomy on parietal cell function in humans. Leth, R., Elander, B., Fellenius, E., Olbe, L., Haglund, U. Gastroenterology (1984) [Pubmed]
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