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Chemical Compound Review

Oxipurinol     3,5,7,8- tetrazabicyclo[4.3.0]nona- 5,9...

Synonyms: Oxypurinol, Alloxanthin, Alloxanthine, DHPP, Ossipurinolo, ...
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Disease relevance of Alloxanthine


Psychiatry related information on Alloxanthine

  • Oxypurinol (40 mg/kg, IP), administered 20 min prior to carotid occlusion, prevented the increase in locomotor activity observed in saline-injected ischemic animals and significantly reduced the damage to, and loss of, CA1 hippocampal neurons observed 5 days postischemia [6].

High impact information on Alloxanthine


Chemical compound and disease context of Alloxanthine


Biological context of Alloxanthine


Anatomical context of Alloxanthine


Associations of Alloxanthine with other chemical compounds

  • The XO reducing substrates xanthine, NADH, and 2,3-dihydroxybenz-aldehyde triggered nitrite reduction to NO, and the molybdenum-binding XO inhibitor oxypurinol inhibited this NO formation, indicating that nitrite reduction occurs at the molybdenum site [20].
  • In agreement with this concept, the enzymatic reduction of CysNO by XO was inhibitable by oxypurinol and diphenyliodonium, inhibitors that interfere with the catalytic cycle at the molybdenum and flavin sites, respectively [21].
  • Male Sprague-Dawley rats were subjected to 35 min of bilateral renal arterial occlusion with or without oxypurinol/benzoate therapy [22].
  • We conclude that the decreased CLR of oxypurinol was the result of the reduced protein content of the diet and the CLR of both inulin and creatinine were decreased on the low-protein diet [23].
  • Inhibition of O2- with superoxide dismutase, oxypurinol, tiron, or the superoxide dismutase mimetic Mn(III)tetrakis(4-benzoic acid)porphyrin chloride did not restore but further deteriorated the relaxation of LPS-treated rings [24].

Gene context of Alloxanthine


Analytical, diagnostic and therapeutic context of Alloxanthine


  1. Chemiluminescence assay of mucosal reactive oxygen metabolites in inflammatory bowel disease. Simmonds, N.J., Allen, R.E., Stevens, T.R., Van Someren, R.N., Blake, D.R., Rampton, D.S. Gastroenterology (1992) [Pubmed]
  2. Allergic reaction to allopurinol with cross-reactivity to oxypurinol. Lockard, O., Harmon, C., Nolph, K., Irvin, W. Ann. Intern. Med. (1976) [Pubmed]
  3. Xanthine oxidase inhibition does not limit canine infarct size. Werns, S.W., Grum, C.M., Ventura, A., Hahn, R.A., Ho, P.P., Towner, R.D., Fantone, J.C., Schork, M.A., Lucchesi, B.R. Circulation (1991) [Pubmed]
  4. Oxypurinol limits myocardial stunning but does not reduce infarct size after reperfusion. Puett, D.W., Forman, M.B., Cates, C.U., Wilson, B.H., Hande, K.R., Friesinger, G.C., Virmani, R. Circulation (1987) [Pubmed]
  5. Severe allopurinol toxicity. Description and guidelines for prevention in patients with renal insufficiency. Hande, K.R., Noone, R.M., Stone, W.J. Am. J. Med. (1984) [Pubmed]
  6. Oxypurinol attenuates ischemia-induced hippocampal damage in the gerbil. Phillis, J.W. Brain Res. Bull. (1989) [Pubmed]
  7. The effect of dietary protein on the clearance of allopurinol and oxypurinol. Berlinger, W.G., Park, G.D., Spector, R. N. Engl. J. Med. (1985) [Pubmed]
  8. Urinary-tract stones resulting from the excretion of oxypurinol. Landgrebe, A.R., Nyhan, W.L., Coleman, M. N. Engl. J. Med. (1975) [Pubmed]
  9. Tumor necrosis factor-alpha-mediated decrease in glutathione increases the sensitivity of pulmonary vascular endothelial cells to H2O2. Ishii, Y., Partridge, C.A., Del Vecchio, P.J., Malik, A.B. J. Clin. Invest. (1992) [Pubmed]
  10. Effect of simultaneous inhibition of TNF-alpha production and xanthine oxidase in experimental acute pancreatitis: the role of mitogen activated protein kinases. Pereda, J., Sabater, L., Cassinello, N., Gómez-Cambronero, L., Closa, D., Folch-Puy, E., Aparisi, L., Calvete, J., Cerdá, M., Lledó, S., Viña, J., Sastre, J. Ann. Surg. (2004) [Pubmed]
  11. Inhibition of xanthine oxidase improves myocardial contractility in patients with ischemic cardiomyopathy. Baldus, S., M??llerleile, K., Chumley, P., Steven, D., Rudolph, V., Lund, G.K., Staude, H.J., Stork, A., K??ster, R., K??hler, J., Weiss, C., M??nzel, T., Meinertz, T., Freeman, B.A., Heitzer, T. Free Radic. Biol. Med. (2006) [Pubmed]
  12. Oxypurinol-enhanced postischemic recovery of the rat brain involves preservation of adenine nucleotides. Phillis, J.W., Perkins, L.M., Smith-Barbour, M., O'Regan, M.H. J. Neurochem. (1995) [Pubmed]
  13. Differential regulation of xanthine and NAD(P)H oxidase by hypoxia in human umbilical vein endothelial cells. Role of nitric oxide and adenosine. Sohn, H.Y., Krotz, F., Gloe, T., Keller, M., Theisen, K., Klauss, V., Pohl, U. Cardiovasc. Res. (2003) [Pubmed]
  14. Xanthine-containing calculi during allopurinol therapy. Kranen, S., Keough, D., Gordon, R.B., Emmerson, B.T. J. Urol. (1985) [Pubmed]
  15. Binding of xanthine oxidase to glycosaminoglycans limits inhibition by oxypurinol. Kelley, E.E., Trostchansky, A., Rubbo, H., Freeman, B.A., Radi, R., Tarpey, M.M. J. Biol. Chem. (2004) [Pubmed]
  16. Beneficial effects of oxypurinol pretreatment in stunned, reperfused canine myocardium. Holzgrefe, H.H., Gibson, J.K. Cardiovasc. Res. (1989) [Pubmed]
  17. Hypoxia/reoxygenation stimulates endothelium to promote neutrophil adhesion. Palluy, O., Morliere, L., Gris, J.C., Bonne, C., Modat, G. Free Radic. Biol. Med. (1992) [Pubmed]
  18. Hypercholesterolemia enhances oxidant production in mesenteric venules exposed to Ischemia/Reperfusion. Kurose, I., Wolf, R.E., Grisham, M.B., Granger, D.N. Arterioscler. Thromb. Vasc. Biol. (1998) [Pubmed]
  19. Oxypurinol improves coronary and peripheral endothelial function in patients with coronary artery disease. Baldus, S., Köster, R., Chumley, P., Heitzer, T., Rudolph, V., Ostad, M.A., Warnholtz, A., Staude, H.J., Thuneke, F., Koss, K., Berger, J., Meinertz, T., Freeman, B.A., Münzel, T. Free Radic. Biol. Med. (2005) [Pubmed]
  20. Characterization of the magnitude and kinetics of xanthine oxidase-catalyzed nitrite reduction. Evaluation of its role in nitric oxide generation in anoxic tissues. Li, H., Samouilov, A., Liu, X., Zweier, J.L. J. Biol. Chem. (2001) [Pubmed]
  21. Xanthine oxidase-mediated decomposition of S-nitrosothiols. Trujillo, M., Alvarez, M.N., Peluffo, G., Freeman, B.A., Radi, R. J. Biol. Chem. (1998) [Pubmed]
  22. An evaluation of antioxidant effects on recovery from postischemic acute renal failure. Zager, R.A., Fuerstenberg, S.M., Baehr, P.H., Myerson, D., Torok-Storb, B. J. Am. Soc. Nephrol. (1994) [Pubmed]
  23. Renal clearances of oxypurinol and inulin on an isocaloric, low-protein diet. Kitt, T.M., Park, G.D., Spector, R., Lawton, W., Tsalikian, E. Clin. Pharmacol. Ther. (1988) [Pubmed]
  24. Role of increased production of superoxide anions by NAD(P)H oxidase and xanthine oxidase in prolonged endotoxemia. Brandes, R.P., Koddenberg, G., Gwinner, W., Kim, D., Kruse, H.J., Busse, R., Mügge, A. Hypertension (1999) [Pubmed]
  25. Cytotoxic mechanisms by M239V presenilin 2, a little-analyzed Alzheimer's disease-causative mutant. Abe, Y., Hashimoto, Y., Tomita, Y., Terashita, K., Aiso, S., Tajima, H., Niikura, T., Matsuoka, M., Nishimoto, I. J. Neurosci. Res. (2004) [Pubmed]
  26. Involvement of uric acid transporter in increased renal clearance of the xanthine oxidase inhibitor oxypurinol induced by a uricosuric agent, benzbromarone. Iwanaga, T., Kobayashi, D., Hirayama, M., Maeda, T., Tamai, I. Drug Metab. Dispos. (2005) [Pubmed]
  27. Xanthine oxidase inhibition by allopurinol affects the reliability of urinary caffeine metabolic ratios as markers for N-acetyltransferase 2 and CYP1A2 activities. Fuchs, P., Haefeli, W.E., Ledermann, H.R., Wenk, M. Eur. J. Clin. Pharmacol. (1999) [Pubmed]
  28. Oxygen radicals mediate the final exacerbation of endothelin-1-induced gastric ulcer in rat. Lazaratos, S., Irukayama-Tomobe, Y., Miyauchi, T., Goto, K., Nakahara, A. Eur. J. Pharmacol. (2001) [Pubmed]
  29. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pacher, P., Nivorozhkin, A., Szabó, C. Pharmacol. Rev. (2006) [Pubmed]
  30. Interaction of milk xanthine oxidase with folic acid. Inhibition of milk xanthine oxidase by folic acid and separation of the enzyme into two fractions on Sepharose 4B/folate gel. Nishino, T., Tsushima, K. J. Biol. Chem. (1986) [Pubmed]
  31. Allopurinol kinetics. Hande, K., Reed, E., Chabner, B. Clin. Pharmacol. Ther. (1978) [Pubmed]
  32. Free radical scavenging and antioxidant activity of allopurinol and oxypurinol in experimental lens-induced uveitis. Augustin, A.J., Böker, T., Blumenröder, S.H., Lutz, J., Spitznas, M. Invest. Ophthalmol. Vis. Sci. (1994) [Pubmed]
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