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Chemical Compound Review

Pimagedine     2-aminoguanidine

Synonyms: aminoguanidine, GER-11, Lopac-A-7009, Lopac-A-8835, Tocris-0787, ...
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Disease relevance of aminoguanidine


Psychiatry related information on aminoguanidine


High impact information on aminoguanidine

  • In a group of diabetic patients treated with the advanced glycosylation inhibitor aminoguanidine, Hb-AGE levels decreased significantly over a 1-month period [10].
  • Aminoguanidine administration to rats was equally effective in preventing diabetes-induced formation of fluorescent advanced nonenzymatic glycosylation products and cross-linking of arterial wall connective tissue protein in vivo [1].
  • Aminoguanidine, a selective inhibitor of the iNOS, inhibited the in vitro production of nitric oxide by cells isolated from individual implantation sites, and more strikingly, significantly reduced early embryo losses in CBA/J females mated by DBA/2 males when given orally or parenterally to the gravid females starting on day 6 of gestation [11].
  • Aminoguanidine treatment prolonged graft survival, improved graft contractile function, and significantly reduced the histologic grade of rejection [12].
  • In addition, aminoguanidine-treated pregnant mice showed a significant increase in average litter size when the pregnancies were allowed to proceed to term.(ABSTRACT TRUNCATED AT 400 WORDS)[11]

Chemical compound and disease context of aminoguanidine


Biological context of aminoguanidine


Anatomical context of aminoguanidine


Associations of aminoguanidine with other chemical compounds

  • In cultured prediabetic ZDF islets, FFA induced a fourfold greater rise in NO, upregulated mRNA of inducible nitric oxide synthase (iNOS), and reduced insulin output; both nicotinamide and aminoguanidine, which lower NO, prevented the FFA-mediated increase in iNOS mRNA, reduced NO, and minimized the loss of insulin secretion [25].
  • Ileal mucosal homogenates from the resection group receiving aminoguanidine, when compared with those from resection controls, showed no diamine oxidase activity with increased putrescine content and ornithine decarboxylase activity [26].
  • Alternatively, administration of aminoguanidine (7.35 mmol x kg(-1) x d(-1)) prevented both the enhanced myocardial collagen fluorescence (7.1+/-1.2) and the increased slope of the linearized LVED stress-LVED strain relation (29+/-2) but did not change markers of blood glucose control [14].
  • Nitric oxide production in islets from nonobese diabetic mice: aminoguanidine-sensitive and -resistant stages in the immunological diabetic process [27].
  • Presumably this occurs because early glycosylation products preferentially bind to aminoguanidine rather than to lysine groups of adjacent proteins [21].

Gene context of aminoguanidine


Analytical, diagnostic and therapeutic context of aminoguanidine


  1. Aminoguanidine prevents diabetes-induced arterial wall protein cross-linking. Brownlee, M., Vlassara, H., Kooney, A., Ulrich, P., Cerami, A. Science (1986) [Pubmed]
  2. Aminoguanidine, an inhibitor of inducible nitric oxide synthase, ameliorates experimental autoimmune encephalomyelitis in SJL mice. Cross, A.H., Misko, T.P., Lin, R.F., Hickey, W.F., Trotter, J.L., Tilton, R.G. J. Clin. Invest. (1994) [Pubmed]
  3. Role of nitric oxide in experimental obliterative bronchiolitis (chronic rejection) in the rat. Kallio, E.A., Koskinen, P.K., Aavik, E., Vaali, K., Lemstöm, K.B. J. Clin. Invest. (1997) [Pubmed]
  4. Inducible nitric oxide synthase is an endogenous neuroprotectant after traumatic brain injury in rats and mice. Sinz, E.H., Kochanek, P.M., Dixon, C.E., Clark, R.S., Carcillo, J.A., Schiding, J.K., Chen, M., Wisniewski, S.R., Carlos, T.M., Williams, D., DeKosky, S.T., Watkins, S.C., Marion, D.W., Billiar, T.R. J. Clin. Invest. (1999) [Pubmed]
  5. Potential role of inducible nitric oxide synthase in the sleep-wake states occurrence in old rats. Clément, P., Sarda, N., Cespuglio, R., Gharib, A. Neuroscience (2005) [Pubmed]
  6. Modulation by alpha-difluoromethyl-ornithine and aminoguanidine of pain threshold, morphine analgesia and tolerance. Lu, G., Su, R.B., Li, J., Qin, B.Y. Eur. J. Pharmacol. (2003) [Pubmed]
  7. Attenuation of morphine tolerance and dependence by aminoguanidine in mice. Abdel-Zaher, A.O., Hamdy, M.M., Aly, S.A., Abdel-Hady, R.H., Abdel-Rahman, S. Eur. J. Pharmacol. (2006) [Pubmed]
  8. Advanced glycation end-products are responsible for the impairment of corpus cavernosal smooth muscle relaxation seen in diabetes. Cartledge, J.J., Eardley, I., Morrison, J.F. BJU international. (2001) [Pubmed]
  9. 3-Nitropropionic acid produces striatum selective lesions accompanied by iNOS expression. Nishino, H., Fujimoto, I., Shimano, Y., Hida, H., Kumazaki, M., Fukuda, A. J. Chem. Neuroanat. (1996) [Pubmed]
  10. Hemoglobin-AGE: a circulating marker of advanced glycosylation. Makita, Z., Vlassara, H., Rayfield, E., Cartwright, K., Friedman, E., Rodby, R., Cerami, A., Bucala, R. Science (1992) [Pubmed]
  11. Early embryo loss is associated with local production of nitric oxide by decidual mononuclear cells. Haddad, E.K., Duclos, A.J., Baines, M.G. J. Exp. Med. (1995) [Pubmed]
  12. Modulation of in vivo alloreactivity by inhibition of inducible nitric oxide synthase. Worrall, N.K., Lazenby, W.D., Misko, T.P., Lin, T.S., Rodi, C.P., Manning, P.T., Tilton, R.G., Williamson, J.R., Ferguson, T.B. J. Exp. Med. (1995) [Pubmed]
  13. Aminoguanidine effects on nerve blood flow, vascular permeability, electrophysiology, and oxygen free radicals. Kihara, M., Schmelzer, J.D., Poduslo, J.F., Curran, G.L., Nickander, K.K., Low, P.A. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  14. Aminoguanidine prevents the decreased myocardial compliance produced by streptozotocin-induced diabetes mellitus in rats. Norton, G.R., Candy, G., Woodiwiss, A.J. Circulation (1996) [Pubmed]
  15. The effect of aminoguanidine and tolrestat on glucose toxicity in bovine retinal capillary pericytes. Chibber, R., Molinatti, P.A., Wong, J.S., Mirlees, D., Kohner, E.M. Diabetes (1994) [Pubmed]
  16. Pyridoxamine, an inhibitor of advanced glycation reactions, also inhibits advanced lipoxidation reactions. Mechanism of action of pyridoxamine. Onorato, J.M., Jenkins, A.J., Thorpe, S.R., Baynes, J.W. J. Biol. Chem. (2000) [Pubmed]
  17. Nitric oxide expression in the spleen, but not in the liver, correlates with resistance to blood-stage malaria in mice. Jacobs, P., Radzioch, D., Stevenson, M.M. J. Immunol. (1995) [Pubmed]
  18. Aminoguanidine treatment increases elasticity and decreases fluid filtration of large arteries from diabetic rats. Huijberts, M.S., Wolffenbuttel, B.H., Boudier, H.A., Crijns, F.R., Kruseman, A.C., Poitevin, P., Lévy, B.I. J. Clin. Invest. (1993) [Pubmed]
  19. Rat Kupffer cell-derived nitric oxide suppresses proliferation and induces apoptosis of syngeneic hepatoma cells. Kurose, I., Higuchi, H., Yonei, Y., Ebinuma, H., Watanabe, N., Hokari, R., Fukumura, D., Miura, S., Takaishi, M., Saito, H., Nakatsumi, R.C., Ishii, H. Gastroenterology (1996) [Pubmed]
  20. Inhibition of inducible nitric oxide synthase ameliorates endotoxin-induced gut mucosal barrier dysfunction in rats. Unno, N., Wang, H., Menconi, M.J., Tytgat, S.H., Larkin, V., Smith, M., Morin, M.J., Chavez, A., Hodin, R.A., Fink, M.P. Gastroenterology (1997) [Pubmed]
  21. Aminoguanidine inhibits oxidative modification of low density lipoprotein protein and the subsequent increase in uptake by macrophage scavenger receptors. Picard, S., Parthasarathy, S., Fruebis, J., Witztum, J.L. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  22. Role of nitric oxide in induction of inflammatory fluid secretion by the mucosa of the feline gallbladder. Nilsson, B., Delbro, D., Hedin, L., Conradi, N., Thune, A., Friman, S., Wennmalm, A., Yan, Z.Q., Svanvik, J. Gastroenterology (1996) [Pubmed]
  23. Serum amine oxidase activity contributes to crisis in mouse embryo cell lines. Parchment, R.E., Lewellyn, A., Swartzendruber, D., Pierce, G.B. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  24. Aminoguanidine treatment inhibits the development of experimental diabetic retinopathy. Hammes, H.P., Martin, S., Federlin, K., Geisen, K., Brownlee, M. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  25. Role of nitric oxide in obesity-induced beta cell disease. Shimabukuro, M., Ohneda, M., Lee, Y., Unger, R.H. J. Clin. Invest. (1997) [Pubmed]
  26. Suppression of diamine oxidase activity enhances postresection ileal proliferation in the rat. Erdman, S.H., Park, J.H., Thompson, J.S., Grandjean, C.J., Hart, M.H., Vanderhoof, J.A. Gastroenterology (1989) [Pubmed]
  27. Nitric oxide production in islets from nonobese diabetic mice: aminoguanidine-sensitive and -resistant stages in the immunological diabetic process. Corbett, J.A., Mikhael, A., Shimizu, J., Frederick, K., Misko, T.P., McDaniel, M.L., Kanagawa, O., Unanue, E.R. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  28. Bidirectional regulation of osteoclast function by nitric oxide synthase isoforms. Brandi, M.L., Hukkanen, M., Umeda, T., Moradi-Bidhendi, N., Bianchi, S., Gross, S.S., Polak, J.M., MacIntyre, I. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  29. Recipient humoral immunity against leukoreduced allogeneic platelets is suppressed by aminoguanidine, a selective inhibitor of inducible nitric oxide synthase. Bang, A., Speck, E.R., Blanchette, V.S., Freedman, J., Semple, J.W. Blood (1996) [Pubmed]
  30. Regulation of the expression of cyclooxygenase-2 by nitric oxide in rat peritoneal macrophages. Habib, A., Bernard, C., Lebret, M., Creminon, C., Esposito, B., Tedgui, A., Maclouf, J. J. Immunol. (1997) [Pubmed]
  31. Nitric oxide and the Th2 response combine to prevent severe hepatic damage during Schistosoma mansoni infection. Brunet, L.R., Beall, M., Dunne, D.W., Pearce, E.J. J. Immunol. (1999) [Pubmed]
  32. TNF-alpha and IL-10 modulate the induction of apoptosis by virulent Mycobacterium tuberculosis in murine macrophages. Rojas, M., Olivier, M., Gros, P., Barrera, L.F., García, L.F. J. Immunol. (1999) [Pubmed]
  33. Aminoguanidine prevents age-related arterial stiffening and cardiac hypertrophy. Corman, B., Duriez, M., Poitevin, P., Heudes, D., Bruneval, P., Tedgui, A., Levy, B.I. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  34. Inhibition of inducible nitric oxide synthase prevents myocardial and systemic vascular barrier dysfunction during early cardiac allograft rejection. Worrall, N.K., Chang, K., Suau, G.M., Allison, W.S., Misko, T.P., Sullivan, P.M., Tilton, R.G., Williamson, J.R., Ferguson, T.B. Circ. Res. (1996) [Pubmed]
  35. Tumor stroma interactions induce chemoresistance in pancreatic ductal carcinoma cells involving increased secretion and paracrine effects of nitric oxide and interleukin-1beta. Müerköster, S., Wegehenkel, K., Arlt, A., Witt, M., Sipos, B., Kruse, M.L., Sebens, T., Klöppel, G., Kalthoff, H., Fölsch, U.R., Schäfer, H. Cancer Res. (2004) [Pubmed]
  36. Pyridoxamine traps intermediates in lipid peroxidation reactions in vivo: evidence on the role of lipids in chemical modification of protein and development of diabetic complications. Metz, T.O., Alderson, N.L., Chachich, M.E., Thorpe, S.R., Baynes, J.W. J. Biol. Chem. (2003) [Pubmed]
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