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Chemical Compound Review

Nitrol     1-nitronaphthalene

Synonyms: CCRIS 450, SureCN57184, CHEMBL165373, NSC-9584, ACMC-1CJ12, ...
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Disease relevance of Nitrol


High impact information on Nitrol

  • This is the first in a series of articles employing this microarray for detecting gene expression changes during acute injury produced by 1-nitronaphthalene and subsequent repair [1].
  • These results suggest the importance of other P450 enzymes in the epoxidation/bioactivation of 1-nitronaphthalene [4].
  • CYP2F4 failed to display an enhanced ability to bioactivate 1-nitronaphthalene, an ability that could have potentially compensated for the lower CYP2F pulmonary expression levels in the rat, yet equal species susceptibilities [4].
  • Accordingly, infant monkey airway subcompartments, including trachea, proximal, midlevel, distal airways, and parenchyma, were incubated with naphthalene or 1-nitronaphthalene to define metabolism at both high (500 microM) and low (50 microM) substrate concentrations [5].
  • This is compared with denudation of 4% of the basement membrane of FA-exposed rats administered 100 mg/kg 1-nitronaphthalene; only 25% of the cells remaining on the epithelium were necrotic [2].

Chemical compound and disease context of Nitrol


Biological context of Nitrol


Anatomical context of Nitrol

  • No differences in the susceptibility of intrapulmonary airways or trachea to 1-nitronaphthalene were observed between filtered air- and ozone-exposed rats [2].
  • To test whether exposure to ozone alters pulmonary cytochrome P450 monooxygenase-mediated metabolism of xenobiotics, rates of 1-nitronaphthalene (1-NN) metabolism were measured in microsomes prepared from trachea, intrapulmonary airways, and distal lung of rats exposed to filtered air (FA) or ozone (O(3)) (0.8 ppm 8 h/day for 90 days) [10].
  • Metabolic fingerprints, in the form of patterns of high-concentration endogenous metabolites, of 1-nitronaphthalene (NN)-induced lung toxicity have been elucidated in bronchoalveolar lavage fluid (BALF), urine, blood plasma, and intact lung and liver tissue using NMR spectroscopy-based metabolic profiling [11].
  • Reactive metabolites of naphthalene and 1-nitronaphthalene covalently bind to proteins, and the formation of covalent adducts correlates with airway epithelial cell injury in rodent models [12].

Associations of Nitrol with other chemical compounds


Analytical, diagnostic and therapeutic context of Nitrol


  1. Gene expression analysis in response to lung toxicants: I. Sequencing and microarray development. Shultz, M.A., Zhang, L., Gu, Y.Z., Baker, G.L., Fannuchi, M.V., Padua, A.M., Gurske, W.A., Morin, D., Penn, S.G., Jovanovich, S.B., Plopper, C.G., Buckpitt, A.R. Am. J. Respir. Cell Mol. Biol. (2004) [Pubmed]
  2. Long-term exposure to ozone increases acute pulmonary centriacinar injury by 1-nitronaphthalene: II. Quantitative histopathology. Paige, R.C., Wong, V., Plopper, C.G. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  3. An ultrastructural evaluation of acute 1-nitronaphthalene induced hepatic and pulmonary toxicity in the rat. Sauer, J.M., Eversole, R.R., Lehmann, C.L., Johnson, D.E., Beuving, L.J. Toxicol. Lett. (1997) [Pubmed]
  4. Bioactivation of the pulmonary toxicants naphthalene and 1-nitronaphthalene by rat CYP2F4. Baldwin, R.M., Shultz, M.A., Buckpitt, A.R. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  5. Site-specific metabolism of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. Boland, B., Lin, C.Y., Morin, D., Miller, L., Plopper, C., Buckpitt, A. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  6. Role of murine cytochrome P-450 2F2 in metabolic activation of naphthalene and metabolism of other xenobiotics. Shultz, M.A., Choudary, P.V., Buckpitt, A.R. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  7. All-trans-retinol alteration of 1-nitronaphthalene-induced pulmonary and hepatic injury by modulation of associated inflammatory responses in the male Sprague-Dawley rat. Sauer, J.M., Hooser, S.B., Sipes, I.G. Toxicol. Appl. Pharmacol. (1995) [Pubmed]
  8. Toxicity of 3-methylindole, 1-nitronaphthalene and paraquat in precision-cut rat lung slices. Price, R.J., Renwick, A.B., Wield, P.T., Beamand, J.A., Lake, B.G. Arch. Toxicol. (1995) [Pubmed]
  9. Genotoxicity of 1-nitronaphthalene in Chinese hamster V79 cells. Boyes, B.G., Rogers, C.G., Stapley, R. Mutat. Res. (1991) [Pubmed]
  10. Long-term exposure to ozone increases acute pulmonary centriacinar injury by 1-nitronaphthalene: I. Region-specific enzyme activity. Paige, R.C., Royce, F.H., Plopper, C.G., Buckpitt, A.R. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  11. Characterization of the biochemical effects of 1-nitronaphthalene in rats using global metabolic profiling by NMR spectroscopy and pattern recognition. Azmi, J., Connelly, J., Holmes, E., Nicholson, J.K., Shore, R.F., Griffin, J.L. Biomarkers (2005) [Pubmed]
  12. Identification of proteins adducted by reactive metabolites of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. Lin, C.Y., Boland, B.C., Lee, Y.J., Salemi, M.R., Morin, D., Miller, L.A., Plopper, C.G., Buckpitt, A.R. Proteomics (2006) [Pubmed]
  13. Glutathione conjugation of electrophilic metabolites of 1-nitronaphthalene in rat tracheobronchial airways and liver: identification by mass spectrometry and proton nuclear magnetic resonance spectroscopy. Watt, K.C., Morin, D.M., Kurth, M.J., Mercer, R.S., Plopper, C.G., Buckpitt, A.R. Chem. Res. Toxicol. (1999) [Pubmed]
  14. all-trans-retinol modulation of nitronaphthalene-induced lung and liver injury in male Sprague-Dawley rats. Sauer, J.M., Sipes, I.G. Proc. West. Pharmacol. Soc. (1995) [Pubmed]
  15. Acute target organ toxicity of 1-nitronaphthalene in the rat. Johnson, D.E., Riley, M.G., Cornish, H.H. Journal of applied toxicology : JAT. (1984) [Pubmed]
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