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Chemical Compound Review

PYRITHIAMINE     2-[1-[(4-amino-2-methyl- pyrimidin-5...

Synonyms: Pyrithiamin, SureCN94765, NSC-76271, NSC-400971, NSC76271, ...
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Disease relevance of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Psychiatry related information on 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


High impact information on 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Chemical compound and disease context of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Biological context of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Anatomical context of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Associations of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol with other chemical compounds


Gene context of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol


Analytical, diagnostic and therapeutic context of 2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-6-methyl-pyridin-5-yl]ethanol

  • We used kinetic assays coupled with mass spectrometry of the reaction products and x-ray crystallography of an equilibrium reaction mixture of thiamine pyrophosphokinase, pyrithiamine, and Mg2+/ATP to elucidate the mechanism by which pyrithiamine inhibits the enzymatic production of thiamine pyrophosphate [10].
  • Microdialysis in the awake, freely moving rat was used to determine the effect of pyrithiamine-induced thiamine deficiency on the levels of amino acids in the brain [32].
  • To help clarify the biochemical basis for these disorders, a cell culture system has been established in which pyrithiamine, a potent thiamine transport inhibitor, was used to mimic different degrees of thiamine deficiency within human lymphoblasts [33].
  • Consequences of long-term consumption of alcohol (20 months) and of pyrithiamine-induced blockade of vitamin-B1-uptake on the shape of individual brain structures and on the acquisition of two learning tasks have been investigated in 3 groups of rats (alcohol group, AL; thiamine-deficient group, TH; control group, CG) [34].
  • To assess retrograde retention of spatial information, half of the rats were pre-trained on the maze before the treatment manipulations of pyrithiamine (PT)-induced thiamine deficiency and post-tested after treatment (pre-trained group) [35].


  1. Model of Wernicke's encephalopathy. Troncoso, J.C., Johnston, M.V., Hess, K.M., Griffin, J.W., Price, D.L. Arch. Neurol. (1981) [Pubmed]
  2. Crystal Structures of the Thi-Box Riboswitch Bound to Thiamine Pyrophosphate Analogs Reveal Adaptive RNA-Small Molecule Recognition. Edwards, T.E., Ferré-D'Amaré, A.R. Structure (2006) [Pubmed]
  3. Effects of pyrithiamin and oxythiamin on acetylcholine levels and utilization in rat brain. Vorhees, C.V., Schmidt, D.E., Barrett, R.J. Brain Res. Bull. (1978) [Pubmed]
  4. Neuronal cell death in Wernicke's encephalopathy: pathophysiologic mechanisms and implications for PET imaging. Leong, D.K., Butterworth, R.F. Metabolic brain disease. (1996) [Pubmed]
  5. Glycolytic metabolism in cultured cells of the nervous system. III. The effects of thiamine deficiency and pyrithiamine on the C-6 glioma and C-1300 neuroblastoma cell lines. Schwartz, J.P., Lust, W.D., Shirazawa, R., Passonneau, J.V. Mol. Cell. Biochem. (1975) [Pubmed]
  6. Early edematous lesion of pyrithiamine induced acute thiamine deficient encephalopathy in the mouse. Watanabe, I., Kanabe, S. J. Neuropathol. Exp. Neurol. (1978) [Pubmed]
  7. Reversible alterations of cerebral gamma-aminobutyric acid in pyrithiamine-treated rats: implications for the pathogenesis of Wernicke's encephalopathy. Héroux, M., Butterworth, R.F. J. Neurochem. (1988) [Pubmed]
  8. Response latency and accuracy on a pretrained nonmatching-to-sample task in rats recovered from pyrithiamine-induced thiamine deficiency. Knoth, R.L., Mair, R.G. Behav. Neurosci. (1991) [Pubmed]
  9. Physiological, biochemical and morphological studies of Baltic salmon yolk-sac fry with an experimental thiamine deficiency: relations to the M74 syndrome. Amcoff, P., Akerman, G., Tjärnlund, U., Börjeson, H., Norrgren, L., Balk, L. Aquat. Toxicol. (2002) [Pubmed]
  10. Pyrithiamine as a substrate for thiamine pyrophosphokinase. Liu, J.Y., Timm, D.E., Hurley, T.D. J. Biol. Chem. (2006) [Pubmed]
  11. Specific inactivation of alpha (+) molecular form of (Na+ + K+)-ATPase by pyrithiamin. Matsuda, T., Iwata, H., Cooper, J.R. J. Biol. Chem. (1984) [Pubmed]
  12. Increased densities of binding sites for the "peripheral-type" benzodiazepine receptor ligand [3H]PK11195 in vulnerable regions of the rat brain in thiamine deficiency encephalopathy. Leong, D.K., Le, O., Oliva, L., Butterworth, R.F. J. Cereb. Blood Flow Metab. (1994) [Pubmed]
  13. Changes in the hippocampus induced by glucose in thiamin deficient rats detected by MRI. Jordan, L.R., Zelaya, F.O., Rose, S.E., Bower, A.J., Galloway, G., Wholohan, T., Nixon, P.F. Brain Res. (1998) [Pubmed]
  14. Difference in phospholipid dependence between two isozymes of brain (Na+ + K+)-ATPase. Matsuda, T., Iwata, H. Biochim. Biophys. Acta (1986) [Pubmed]
  15. Acute changes in myo-inositol uptake and 22Na+ flux in murine neuroblastoma cells (N1E-115) following insulin. Dunlop, M., Dimitriadis, E., Larkins, R.G. FEBS Lett. (1987) [Pubmed]
  16. Metabolic studies of the edematous cerebral cortex of the pyrithiamine-treated thiamine-deficient rat. Takahashi, H., Nakazawa, S., Yoshino, Y., Shimura, T. Brain Res. (1988) [Pubmed]
  17. Thiamine deficiency-induced disruptions in the diurnal rhythm and regulation of body temperature in the rat. Langlais, P.J., Hall, T. Metabolic brain disease. (1998) [Pubmed]
  18. The role of thiamine on excitable membrane of crayfish giant axon. Sasa, M., Takemoto, I., Nishino, K., Itokawa, Y. J. Nutr. Sci. Vitaminol. (1976) [Pubmed]
  19. Effect of thiamine deficiency, pyrithiamine and oxythiamine on pyruvate metabolism in rat liver and brain in vivo. Meghal, S.K., O'Neal, R.M., Koeppe, R.E. J. Nutr. Sci. Vitaminol. (1977) [Pubmed]
  20. Selective down-regulation of the astrocyte glutamate transporters GLT-1 and GLAST within the medial thalamus in experimental Wernicke's encephalopathy. Hazell, A.S., Rao, K.V., Danbolt, N.C., Pow, D.V., Butterworth, R.F. J. Neurochem. (2001) [Pubmed]
  21. Effect of pyrithiamine treatment and subsequent thiamine rehabilitation on regional cerebral amino acids and thiamine-dependent enzymes. Butterworth, R.F., Héroux, M. J. Neurochem. (1989) [Pubmed]
  22. Comparison of the effects of some thiamine analogues upon thiamine transport across the blood-brain barrier of the rat. Greenwood, J., Pratt, O.E. J. Physiol. (Lond.) (1985) [Pubmed]
  23. Axonal contact regulates expression of alpha2 and beta2 isoforms of Na+, K+-ATPase in Schwann cells: adhesion molecules and nerve regeneration. Kawai, H., Yasuda, H., Terada, M., Omatsu-Kanbe, M., Kikkawa, R. J. Neurochem. (1997) [Pubmed]
  24. Thiamin transport by human erythrocytes and ghosts. Casirola, D., Patrini, C., Ferrari, G., Rindi, G. J. Membr. Biol. (1990) [Pubmed]
  25. Changes in serotonergic neurons in the brain of pyrithiamine-induced acute thiamine-deficient mice. Matsushita, H., Takeuchi, Y., Kosaka, K., Fushiki, S., Kawata, M., Sawada, T. Acta Neuropathol. (1999) [Pubmed]
  26. Characteristics of thiamin transport in the isolated perfused guinea pig heart. Mitrović, D.M., Rosić, M.A., Mojović, M., Nestorović, J., Kostić, M. Archives internationales de physiologie, de biochimie et de biophysique. (1993) [Pubmed]
  27. Effects of thiamin on vitamin B6 synthesis in yeasts. Minami, J., Kishi, T., Kondo, M. J. Gen. Microbiol. (1982) [Pubmed]
  28. Identification and characterization of the thiamine transporter gene of Saccharomyces cerevisiae. Singleton, C.K. Gene (1997) [Pubmed]
  29. Cortical and subcortical white matter damage without Wernicke's encephalopathy after recovery from thiamine deficiency in the rat. Langlais, P.J., Zhang, S.X. Alcohol. Clin. Exp. Res. (1997) [Pubmed]
  30. Activities of thiamine-dependent enzymes in two experimental models of thiamine-deficiency encephalopathy: 1. The pyruvate dehydrogenase complex. Butterworth, R.F., Giguere, J.F., Besnard, A.M. Neurochem. Res. (1985) [Pubmed]
  31. Biochemical studies of pyrithiamine-resistant mutants of Escherichia coli K12. Kawasaki, T., Sanemori, H., Egi, Y., Yoshida, S., Yamada, K. J. Biochem. (1976) [Pubmed]
  32. Cerebral vulnerability is associated with selective increase in extracellular glutamate concentration in experimental thiamine deficiency. Hazell, A.S., Butterworth, R.F., Hakim, A.M. J. Neurochem. (1993) [Pubmed]
  33. Thiamine pyrophosphate-requiring enzymes are altered during pyrithiamine-induced thiamine deficiency in cultured human lymphoblasts. Pekovich, S.R., Martin, P.R., Singleton, C.K. J. Nutr. (1996) [Pubmed]
  34. Widespread neuroanatomical damage and learning deficits following chronic alcohol consumption or vitamin-B1 (thiamine) deficiency in rats. Irle, E., Markowitsch, H.J. Behav. Brain Res. (1983) [Pubmed]
  35. Cholinergic parameters and the retrieval of learned and re-learned spatial information: a study using a model of Wernicke-Korsakoff Syndrome. Pires, R.G., Pereira, S.R., Oliveira-Silva, I.F., Franco, G.C., Ribeiro, A.M. Behav. Brain Res. (2005) [Pubmed]
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