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Chemical Compound Review

xanthine     3,7-dihydropurine-2,6-dione

Synonyms: Xanthin, Dioxopurine, Isoxanthine, Pseudoxanthine, PubChem9186, ...
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Disease relevance of xanthine

  • The primary source of superoxide in reperfused reoxygenated tissues appears to be the enzyme xanthine oxidase, released during ischemia by a calcium-triggered proteolytic attack on xanthine dehydrogenase [1].
  • Xanthine oxidase, which is responsible for the generation of oxygen free radicals, was elevated in serum and lung tissue of mice infected with influenza virus [2].
  • These results suggest that, in low flow hypoxia, early reductive stress plays a key role in the initiation of xanthine oxidase-mediated midzonal oxidative changes, which may lead to subsequent centrilobular necrosis [3].
  • Xanthine oxidase is an important source of reactive oxygen species during ischemia-reperfusion injury, but not in all organs or species [4].
  • Xanthine oxidase (0.003 and 0.012 U/ml) caused lung edema that was attenuated by coinfusion of washed human platelets [5].

Psychiatry related information on xanthine


High impact information on xanthine


Chemical compound and disease context of xanthine


Biological context of xanthine


Anatomical context of xanthine

  • Extensive osseous tophi, resorbed rapidly during therapy with this xanthine oxidase inhibitor and not replaced by new bone matrix, were responsible for the deformity [24].
  • Providing normal macrophages with an exogenous source of oxidative metabolites generated by xanthine and xanthine oxidase, but not glucose and glucose oxidase, resulted in inhibition of intracellular toxoplasma growth [25].
  • Treatment of normal resting human lymphocytes with xanthine oxidase and hypoxanthine dose-dependently induced DNA strand breaks and triggered the rapid synthesis of poly(ADP-ribose) [26].
  • To investigate mechanisms whereby oxidant injury of cells results in cell dysfunction and death, cultured endothelial cells or P388D1 murine macrophage-like cells were exposed to oxidants including H2O2, O2-. (generated by the enzymatic oxidation of xanthine), or to stimulated polymorphonuclear leukocytes (PMN) [27].
  • Parasites were cultured in human group O+ erythrocytes in medium supplemented, as required, with xanthine oxidase or chloroquine [19].

Associations of xanthine with other chemical compounds

  • Three methyl xanthine inhibitors of adenosine 3',5'-monophosphate phosphodiesterase-theophylline, aminophyline, and caffeine-lengthen the period of the circadian conidiation rhythm of Neurospora [28].
  • Xanthine plus xanthine oxidase reversibly stimulated these three parameters of endothelial cell function at doses that were not cytotoxic, as measured by chromium release, adenine uptake, and vital dye exclusion [29].
  • Allopurinol, a competitive inhibitor of xanthine oxidase, has been shown to have a protective effect on ischemic myocardium, but its mechanism of action remains controversial [30].
  • Moreover, prior addition of catalase inhibited both vasoconstriction and the thromboxane B2 production seen in isolated lungs following injection of purine plus xanthine oxidase [31].
  • PMA-activated PMNs or xanthine oxidase plus acetaldehyde were added to target erythrocytes in amounts that provided similar levels of superoxide [32].
  • We report additional crystal structures of as-isolated, functional xanthine oxidase in the course of reaction with the pterin substrate lumazine at 2.2 A resolution and of the nonfunctional desulfo form of the enzyme in complex with xanthine at 2.6 A resolution [33].

Gene context of xanthine


Analytical, diagnostic and therapeutic context of xanthine


  1. Oxygen-derived free radicals in postischemic tissue injury. McCord, J.M. N. Engl. J. Med. (1985) [Pubmed]
  2. Oxygen radicals in influenza-induced pathogenesis and treatment with pyran polymer-conjugated SOD. Oda, T., Akaike, T., Hamamoto, T., Suzuki, F., Hirano, T., Maeda, H. Science (1989) [Pubmed]
  3. Prostaglandin E1 abrogates early reductive stress and zone-specific paradoxical oxidative injury in hypoperfused rat liver. Suzuki, H., Suematsu, M., Ishii, H., Kato, S., Miki, H., Mori, M., Ishimura, Y., Nishino, T., Tsuchiya, M. J. Clin. Invest. (1994) [Pubmed]
  4. Role of cytochrome P-450 in reperfusion injury of the rabbit lung. Bysani, G.K., Kennedy, T.P., Ky, N., Rao, N.V., Blaze, C.A., Hoidal, J.R. J. Clin. Invest. (1990) [Pubmed]
  5. Human platelets modulate edema formation in isolated rabbit lungs. Heffner, J.E., Cook, J.A., Halushka, P.V. J. Clin. Invest. (1989) [Pubmed]
  6. Reductive half-reaction of xanthine oxidase: mechanistic role of the species giving rise to the "rapid type 1" molybdenum(V) electron paramagnetic resonance signal. Hille, R., Kim, J.H., Hemann, C. Biochemistry (1993) [Pubmed]
  7. Dose-response effects of 8-cyclopropyltheophylline on sleep and wakefulness in rats. Radulovacki, M., Virus, R.M. Psychopharmacology (Berl.) (1988) [Pubmed]
  8. Placebo-controlled trial of the xanthine derivative propentofylline in dementia. Möller, H.J., Maurer, I., Saletu, B. Pharmacopsychiatry (1994) [Pubmed]
  9. Clinical trials in dementia with propentofylline. Kittner, B., Rössner, M., Rother, M. Ann. N. Y. Acad. Sci. (1997) [Pubmed]
  10. Brain distribution characteristics of xanthine derivatives and relation to their locomotor activity in mice. Haghgoo, S., Hasegawa, T., Nadai, M., Wang, L., Ishigaki, T., Miyamoto, K., Nabeshima, T. J. Pharm. Pharmacol. (1995) [Pubmed]
  11. Localization of xanthine oxidase in mammary-gland epithelium and capillary endothelium. Jarasch, E.D., Grund, C., Bruder, G., Heid, H.W., Keenan, T.W., Franke, W.W. Cell (1981) [Pubmed]
  12. Cyclic AMP in relation to proliferation of the epidermal cell: a new view. Green, H. Cell (1978) [Pubmed]
  13. Saturnine gout: lead-induced formation of guanine crystals. Farkas, W.R., Stanawitz, T., Schneider, M. Science (1978) [Pubmed]
  14. Pseudomonas and neutrophil products modify transferrin and lactoferrin to create conditions that favor hydroxyl radical formation. Britigan, B.E., Edeker, B.L. J. Clin. Invest. (1991) [Pubmed]
  15. Oxygen free radicals in ischemic acute renal failure in the rat. Paller, M.S., Hoidal, J.R., Ferris, T.F. J. Clin. Invest. (1984) [Pubmed]
  16. Dependence on O2- generation by xanthine oxidase of pathogenesis of influenza virus infection in mice. Akaike, T., Ando, M., Oda, T., Doi, T., Ijiri, S., Araki, S., Maeda, H. J. Clin. Invest. (1990) [Pubmed]
  17. Selection for animal cells that express the Escherichia coli gene coding for xanthine-guanine phosphoribosyltransferase. Mulligan, R.C., Berg, P. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  18. Transcriptional control of the endogenous MYC protooncogene by antisense RNA. Yokoyama, K., Imamoto, F. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  19. Xanthine oxidase inhibits growth of Plasmodium falciparum in human erythrocytes in vitro. Berman, P.A., Human, L., Freese, J.A. J. Clin. Invest. (1991) [Pubmed]
  20. Evidence for enhanced vascular superoxide anion production in nitrate tolerance. A novel mechanism underlying tolerance and cross-tolerance. Münzel, T., Sayegh, H., Freeman, B.A., Tarpey, M.M., Harrison, D.G. J. Clin. Invest. (1995) [Pubmed]
  21. Inhibition of endotoxin-induced bacterial translocation in mice. Deitch, E.A., Ma, L., Ma, W.J., Grisham, M.B., Granger, D.N., Specian, R.D., Berg, R.D. J. Clin. Invest. (1989) [Pubmed]
  22. Bioactivation of mitomycin C by xanthine dehydrogenase from EMT6 mouse mammary carcinoma tumors. Gustafson, D.L., Pritsos, C.A. J. Natl. Cancer Inst. (1992) [Pubmed]
  23. Regulation of xanthine dehydrogenase and xanthine oxidase activity and gene expression in cultured rat pulmonary endothelial cells. Dupont, G.P., Huecksteadt, T.P., Marshall, B.C., Ryan, U.S., Michael, J.R., Hoidal, J.R. J. Clin. Invest. (1992) [Pubmed]
  24. Allopurinol-associated hand and foot deformities in chronic tophaceous gout. Gottlieb, N.L., Gray, R.G. JAMA (1977) [Pubmed]
  25. Macrophage oxygen-dependent antimicrobial activity. II. The role of oxygen intermediates. Murray, H.W., Juangbhanich, C.W., Nathan, C.F., Cohn, Z.A. J. Exp. Med. (1979) [Pubmed]
  26. Lymphocyte dysfunction after DNA damage by toxic oxygen species. A model of immunodeficiency. Carson, D.A., Seto, S., Wasson, D.B. J. Exp. Med. (1986) [Pubmed]
  27. Alterations in adenosine triphosphate and energy charge in cultured endothelial and P388D1 cells after oxidant injury. Spragg, R.G., Hinshaw, D.B., Hyslop, P.A., Schraufstätter, I.U., Cochrane, C.G. J. Clin. Invest. (1985) [Pubmed]
  28. Circadian periodicity a neurospora: alteration by inhibitors of cyclic AMP phosphodiesterase. Feldman, J.F. Science (1975) [Pubmed]
  29. Differential effects of hydrogen peroxide on indices of endothelial cell function. Ager, A., Gordon, J.L. J. Exp. Med. (1984) [Pubmed]
  30. Allopurinol enhanced adenine nucleotide repletion after myocardial ischemia in the isolated rat heart. Lasley, R.D., Ely, S.W., Berne, R.M., Mentzer, R.M. J. Clin. Invest. (1988) [Pubmed]
  31. Oxygen metabolites stimulate thromboxane production and vasoconstriction in isolated saline-perfused rabbit lungs. Tate, R.M., Morris, H.G., Schroeder, W.R., Repine, J.E. J. Clin. Invest. (1984) [Pubmed]
  32. Oxygen radical-induced erythrocyte hemolysis by neutrophils. Critical role of iron and lactoferrin. Vercellotti, G.M., van Asbeck, B.S., Jacob, H.S. J. Clin. Invest. (1985) [Pubmed]
  33. Substrate Orientation and Catalysis at the Molybdenum Site in Xanthine Oxidase: CRYSTAL STRUCTURES IN COMPLEX WITH XANTHINE AND LUMAZINE. Pauff, J.M., Cao, H., Hille, R. J. Biol. Chem. (2009) [Pubmed]
  34. Response to ischemia-reperfusion injury in hypertrophic heart. Role of free-radical metabolic pathways. Batist, G., Mersereau, W., Malashenko, B.A., Chiu, R.C. Circulation (1989) [Pubmed]
  35. Environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H:quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosols. Arlt, V.M., Stiborova, M., Henderson, C.J., Osborne, M.R., Bieler, C.A., Frei, E., Martinek, V., Sopko, B., Wolf, C.R., Schmeiser, H.H., Phillips, D.H. Cancer Res. (2005) [Pubmed]
  36. Photodynamic therapy mediated induction of early response genes. Luna, M.C., Wong, S., Gomer, C.J. Cancer Res. (1994) [Pubmed]
  37. The aldehyde oxidase gene cluster in mice and rats. Aldehyde oxidase homologue 3, a novel member of the molybdo-flavoenzyme family with selective expression in the olfactory mucosa. Kurosaki, M., Terao, M., Barzago, M.M., Bastone, A., Bernardinello, D., Salmona, M., Garattini, E. J. Biol. Chem. (2004) [Pubmed]
  38. 15-deoxy-delta 12,14-prostaglandin J2 induces heme oxygenase-1 gene expression in a reactive oxygen species-dependent manner in human lymphocytes. Alvarez-Maqueda, M., El Bekay, R., Alba, G., Monteseirín, J., Chacón, P., Vega, A., Martín-Nieto, J., Bedoya, F.J., Pintado, E., Sobrino, F. J. Biol. Chem. (2004) [Pubmed]
  39. Xanthine oxidase produces hydrogen peroxide which contributes to reperfusion injury of ischemic, isolated, perfused rat hearts. Brown, J.M., Terada, L.S., Grosso, M.A., Whitmann, G.J., Velasco, S.E., Patt, A., Harken, A.H., Repine, J.E. J. Clin. Invest. (1988) [Pubmed]
  40. High concentrations of antibodies to xanthine oxidase in human and animal sera. Molecular characterization. Bruder, G., Jarasch, E.D., Heid, H.W. J. Clin. Invest. (1984) [Pubmed]
  41. Circulating xanthine oxidase and neutrophil activation during human liver transplantation. Pesonen, E.J., Linder, N., Raivio, K.O., Sarnesto, A., Lapatto, R., Höckerstedt, K., Mäkisalo, H., Andersson, S. Gastroenterology (1998) [Pubmed]
  42. Microencapsulated xanthine oxidase as experimental therapy in Lesch-Nyhan disease. Palmour, R.M., Goodyer, P., Reade, T., Chang, T.M. Lancet (1989) [Pubmed]
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