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Chemical Compound Review

Levoxine     hydrazine

Synonyms: Amerzine, Hydrazin, Diamine, Diazane, HYDRAZINE, ...
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Disease relevance of Hydrazines


Psychiatry related information on Hydrazines

  • We now report evidence that these biometals also mediate the deposition of Abeta amyloid in Alzheimer's disease, since the solubilization of Abeta from post-mortem brain tissue was significantly increased by the presence of chelators, EGTA, N,N,N',N'-tetrakis(2-pyridyl-methyl) ethylene diamine, and bathocuproine [6].
  • In a time-response study, rats were given 90 mg hydrazine/kg body wt. and killed 0.25 to 96 h later [7].
  • The polyamine spermidine, and its diamine precursor, putrescine, blocked CPP-induced darting behavior, as well as CPP-induced hyperactivity, at doses which did not decrease locomotor activity when administered alone [8].
  • L-tryptophan (L-T) was added at a dose of 150-450 mg daily to eight Parkinsonian patients who developed visual hallucinations with paranoidal features under L-dopa (L-D) treatment (112.5-75 mg daily) in combination with alpha-methyldopa hydrazine (12.5-75 mg daily) [9].
  • Residual neurobehavioral impairment in concentration, comprehension, memory, task performance and mood status persisted in a water technician with respiratory and dermal exposures to hydrazine-containing mixtures prior to treatment with steroids for concurrent thrombocytopenia [10].

High impact information on Hydrazines

  • The acetylation polymorphism concerns the metabolism of a variety of arylamine and hydrazine drugs, as well as carcinogens by the cytosolic N-acetyltransferase NAT2 [11].
  • There are no conclusive data on the drug as a human carcinogen, but one of its metabolites, hydrazine (CAS: 302-01-2), has been shown to be carcinogenic in rats and mice [12].
  • Indirect alkylation of CBA mouse liver DNA and RNA by hydrazine in vivo. A possible mechanism of action as a carcinogen [13].
  • In humans they are known to be responsible for the acetylation of a number of arylamine and hydrazine drugs, and they are strongly linked to the carcinogenic potentiation of certain foreign substances [14].
  • The NMR line shape parameters require rapid exchange of the steroid diamine among potential binding sites and are consistent with greater segmental flexibility in the complex compared to the synthetic DNA in solution [15].

Chemical compound and disease context of Hydrazines


Biological context of Hydrazines

  • These results suggest that "indirect" alkylation of nucleic acids is a mechanism of cancer initiation by hydrazine [13].
  • The nonexchangeable proton chemical shift parameters for the dipyrandium.poly(dA-dT) complex demonstrate unstacking of base pairs and partial insertion of the steroid diamine at the complexation site [15].
  • The structure of the hexasaccharide was determined to be NeuAc alpha 2----3Gal beta 1----3[NeuAc alpha 2----3Gal beta 1----4GlNAc beta 1----6]GalNAc, on the basis of exoglycosidase digestion, periodate oxidation, and methylation analysis as well as hydrazine-nitrous acid fragmentation [20].
  • A possibility that the hydrogen atom releasing compound participates in hydrazine plus Cu(II)-induced DNA damage is discussed [21].
  • Spectroscopic and kinetics studies of the inhibition of pig kidney diamine oxidase by anions [22].

Anatomical context of Hydrazines

  • Immunohistochemical examinations showed that mAb 91.9H bound normal colonic epithelial cells, which also stained with high-iron diamine, more strongly than it bound colon carcinoma cells [23].
  • Cell membranes containing pulse-radiolabeled VSG were incubated with hydrazine, and the VSG released from the membranes was measured by carbonate extraction, immunoprecipitation, and SDS-polyacrylamide gel electrophoresis/fluorography [24].
  • Export of the diamine putrescine was studied using inside-out plasma membrane vesicles prepared from Chinese hamster cells [25].
  • Nasal cavities were fixed with Karnovsky's fixative, decalcified, and processed for light microscopy, and sections were stained with alcian blue (pH 2.5)/periodic acid-Schiff or high iron diamine [26].
  • MV, isolated from growth plate cartilage, were analyzed directly by solid-state 31P NMR, or incubated with hydrazine or NaOCl to remove organic constituents [27].

Associations of Hydrazines with other chemical compounds


Gene context of Hydrazines

  • Simultaneous histochemistry with high iron diamine and immunohistochemistry indicated that the increase of detectable MUC2 is concomitant with low mucin sulphation in the same cells [31].
  • Enzyme activity assays show that ATAO1 preferentially oxidizes the aliphatic diamine putrescine with production of the corresponding aldehyde, ammonia and hydrogen peroxide, a recognized plant signal molecule and substrate for peroxidases [32].
  • Arylamine N-acetyltransferase catalyses the N-acetylation of primary arylamine and hydrazine drugs and chemicals [33].
  • N-1-(4-Sulfamoylphenyl)-N-4-pentafluorophenyl-thiosemicarbazide was prepared by the reaction of 4-isothiocyanato-benzenesulfonamide with pentafluorophenyl hydrazine, and proved to be an effective inhibitor of several isozymes of the zinc enzyme carbonic anhydrase (CA, EC, such as CA I, II, and IX [34].
  • Adrenalectomized rats metabolize the diamine at a reduced rate, a result consistent with the previously demonstrated decrease of DAO in the tissues of several species of animal [35].

Analytical, diagnostic and therapeutic context of Hydrazines


  1. Hydrazine and lupus. Durant, P.J., Harris, R.A. N. Engl. J. Med. (1980) [Pubmed]
  2. Complement fixation by rheumatoid factor. Tanimoto, K., Cooper, N.R., Johnson, J.S., Vaughan, J.H. J. Clin. Invest. (1975) [Pubmed]
  3. Intestinal diamine oxidase and histamine release in rabbit mesenteric ischemia. Kusche, J., Lorenz, W., Stahlknecht, C.D., Richter, H., Hesterberg, R., Schmal, A., Hinterlang, E., Weber, D., Ohmann, C. Gastroenterology (1981) [Pubmed]
  4. Adherence of Helicobacter pylori to areas of incomplete intestinal metaplasia in the gastric mucosa. Genta, R.M., Gürer, I.E., Graham, D.Y., Krishnan, B., Segura, A.M., Gutierrez, O., Kim, J.G., Burchette, J.L. Gastroenterology (1996) [Pubmed]
  5. High-dose samarium-153 ethylene diamine tetramethylene phosphonate: low toxicity of skeletal irradiation in patients with osteosarcoma and bone metastases. Anderson, P.M., Wiseman, G.A., Dispenzieri, A., Arndt, C.A., Hartmann, L.C., Smithson, W.A., Mullan, B.P., Bruland, O.S. J. Clin. Oncol. (2002) [Pubmed]
  6. Aqueous dissolution of Alzheimer's disease Abeta amyloid deposits by biometal depletion. Cherny, R.A., Legg, J.T., McLean, C.A., Fairlie, D.P., Huang, X., Atwood, C.S., Beyreuther, K., Tanzi, R.E., Masters, C.L., Bush, A.I. J. Biol. Chem. (1999) [Pubmed]
  7. Methylation of liver DNA guanine in hydrazine hepatotoxicity: dose-response and kinetic characteristics of 7-methylguanine and O6-methylguanine formation and persistence in rats. Becker, R.A., Barrows, L.R., Shank, R.C. Carcinogenesis (1981) [Pubmed]
  8. Polyamines inhibit N-methyl-D-aspartate antagonist-induced darting behavior in the rat prefrontal cortex. Crawley, J.N., Evers, J.R., Paul, S.M. Brain Res. (1992) [Pubmed]
  9. L-tryptophan administration in L-dopa-induced hallucinations in elderly Parkinsonian patients. Rabey, J.M., Vardi, J., Askenazi, J.J., Streifler, M. Gerontology. (1977) [Pubmed]
  10. Residual neurobehavioral impairment in a water technician exposed to hydrazine-containing mixtures. Richter, E.D., Gal, A., Bitchatchi, E., Reches, A. Isr. J. Med. Sci. (1992) [Pubmed]
  11. Molecular mechanisms of genetic polymorphisms of drug metabolism. Meyer, U.A., Zanger, U.M. Annu. Rev. Pharmacol. Toxicol. (1997) [Pubmed]
  12. Hydralazine and breast cancer. Kaufman, D.W., Kelly, J.P., Rosenberg, L., Stolley, P.D., Schottenfeld, D., Shapiro, S. J. Natl. Cancer Inst. (1987) [Pubmed]
  13. Indirect alkylation of CBA mouse liver DNA and RNA by hydrazine in vivo. A possible mechanism of action as a carcinogen. Quintero-Ruiz, A., Paz-Neri, L.L., Villa-Treviño, S. J. Natl. Cancer Inst. (1981) [Pubmed]
  14. Structure of arylamine N-acetyltransferase reveals a catalytic triad. Sinclair, J.C., Sandy, J., Delgoda, R., Sim, E., Noble, M.E. Nat. Struct. Biol. (2000) [Pubmed]
  15. Steroid diamine-nucleic acid interactions: partial insertion of dipyrandium between unstacked base pairs of the poly(dA-dT) duplex in solution. Patel, D.J., Canuel, L.L. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  16. Methylazoxyprocarbazine, the active metabolite responsible for the anticancer activity of procarbazine against L1210 leukemia. Swaffar, D.S., Horstman, M.G., Jaw, J.Y., Thrall, B.D., Meadows, G.G., Harker, W.G., Yost, G.S. Cancer Res. (1989) [Pubmed]
  17. High-dose samarium-153 ethylene diamine tetramethylene phosphonate: low toxicity of skeletal irradiation in patients with osteosarcoma and bone metastases. Franzius, C., Schuck, A., Bielack, S.S. J. Clin. Oncol. (2002) [Pubmed]
  18. Assessment of interchangeability of two brands of levothyroxine preparations with a third-generation TSH assay. Escalante, D.A., Arem, N., Arem, R. Am. J. Med. (1995) [Pubmed]
  19. In vivo rat hemoglobin thiyl free radical formation following phenylhydrazine administration. Maples, K.R., Jordan, S.J., Mason, R.P. Mol. Pharmacol. (1988) [Pubmed]
  20. Presence of an O-glycosidically linked hexasaccharide in fetuin. Edge, A.S., Spiro, R.G. J. Biol. Chem. (1987) [Pubmed]
  21. Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions. The role of hydroxyl radical and hydrogen atom. Yamamoto, K., Kawanishi, S. J. Biol. Chem. (1991) [Pubmed]
  22. Spectroscopic and kinetics studies of the inhibition of pig kidney diamine oxidase by anions. Dooley, D.M., Golnik, K.C. J. Biol. Chem. (1983) [Pubmed]
  23. Human colonic sulfomucin identified by a specific monoclonal antibody. Irimura, T., Wynn, D.M., Hager, L.G., Cleary, K.R., Ota, D.M. Cancer Res. (1991) [Pubmed]
  24. A cell-free assay for glycosylphosphatidylinositol anchoring in African trypanosomes. Demonstration of a transamidation reaction mechanism. Sharma, D.K., Vidugiriene, J., Bangs, J.D., Menon, A.K. J. Biol. Chem. (1999) [Pubmed]
  25. Characterization of a diamine exporter in Chinese hamster ovary cells and identification of specific polyamine substrates. Xie, X., Gillies, R.J., Gerner, E.W. J. Biol. Chem. (1997) [Pubmed]
  26. Effects of an ambient level of ozone on primate nasal epithelial mucosubstances. Quantitative histochemistry. Harkema, J.R., Plopper, C.G., Hyde, D.M., St George, J.A., Dungworth, D.L. Am. J. Pathol. (1987) [Pubmed]
  27. Physicochemical characterization of the nucleational core of matrix vesicles. Wu, L.N., Genge, B.R., Dunkelberger, D.G., LeGeros, R.Z., Concannon, B., Wuthier, R.E. J. Biol. Chem. (1997) [Pubmed]
  28. Mechanism of toxicity of putrescine in Anacystis nidulans. Guarino, L.A., Cohen, S.S. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  29. Synthetic and naturally occurring hydrazines as possible cancer causative agents. Toth, B. Cancer Res. (1975) [Pubmed]
  30. Inhibition and reactivation of Mn-catalase. Implications for valence changes at the active site manganese. Kono, Y., Fridovich, I. J. Biol. Chem. (1983) [Pubmed]
  31. Defective post-transcriptional processing of MUC2 mucin in ulcerative colitis and in Crohn's disease increases detectability of the MUC2 protein core. Hanski, C., Born, M., Foss, H.D., Marowski, B., Mansmann, U., Arastéh, K., Bachler, B., Papenfuss, M., Niedobitek, F. J. Pathol. (1999) [Pubmed]
  32. Developmental expression and biochemical analysis of the Arabidopsis atao1 gene encoding an H2O2-generating diamine oxidase. Møller, S.G., McPherson, M.J. Plant J. (1998) [Pubmed]
  33. Genotyping human polymorphic arylamine N-acetyltransferase: identification of new slow allotypic variants. Hickman, D., Risch, A., Camilleri, J.P., Sim, E. Pharmacogenetics (1992) [Pubmed]
  34. Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II. Di Fiore, A., De Simone, G., Menchise, V., Pedone, C., Casini, A., Scozzafava, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  35. Putrescine metabolism and the study of diamine oxidase activity in vivo. Sourkes, T.L., Missala, K. Agents Actions (1981) [Pubmed]
  36. Acetylator phenotype and metabolic disposition of isoniazid in Japanese patients with systemic lupus erythematosus. Ishizaki, T., Horai, Y., Koya, G., Matsuyama, K., Iguchi, S. Arthritis Rheum. (1981) [Pubmed]
  37. Enzymatic activation of hydrazine derivatives. A spin-trapping study. Sinha, B.K. J. Biol. Chem. (1983) [Pubmed]
  38. Abnormal glycosylation of human cellular fibronectin in the presence of swainsonine. Arumugham, R.G., Tanzer, M.L. J. Biol. Chem. (1983) [Pubmed]
  39. Functional relationships of the genetic locus encoding the glycosyltransferase enzymes involved in expression of the lacto-N-neotetraose terminal lipopolysaccharide structure in Neisseria meningitidis. Wakarchuk, W., Martin, A., Jennings, M.P., Moxon, E.R., Richards, J.C. J. Biol. Chem. (1996) [Pubmed]
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