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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Chlorooxirane     2-chlorooxirane

Synonyms: CCRIS 861, AG-H-10881, CHEBI:29129, AC1L2NGJ, AC1Q3PNZ, ...
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Disease relevance of CHLOROETHYLENE OXIDE


High impact information on CHLOROETHYLENE OXIDE


Biological context of CHLOROETHYLENE OXIDE


Anatomical context of CHLOROETHYLENE OXIDE

  • The applicability of the method was established by determining epsilon Gua in rats treated with CEO by portal vein injection and an unexposed human liver [8].

Associations of CHLOROETHYLENE OXIDE with other chemical compounds




Analytical, diagnostic and therapeutic context of CHLOROETHYLENE OXIDE

  • In this study, we report the detection of epsilonA in the urine of rats exposed to chloroethylene oxide (CEO) using immunoaffinity columns made with specific monoclonal antibodies for enrichment, followed by quantitation by HPLC with fluorescence detection [14].
  • Analysis of 1,N2-ethenoguanine and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine in DNA treated with 2-chlorooxirane by high performance liquid chromatography/electrospray mass spectrometry and comparison of amounts to other DNA adducts [15].
  • Chloracetaldehyde and chloroethylene oxide both produced similar effects on the first wave of DNA synthesis after partial hepatectomy, inhibiting the DNA synthesis rate by approx. 50% [16].
  • We observed a K-ras-2 mutation pattern characteristic of chloroethylene oxide, one of the carcinogenic metabolites of VC analysed in animal models [17].


  1. Lack of miscoding properties of 7-(2-oxoethyl)guanine, the major vinyl chloride-DNA adduct. Barbin, A., Laib, R.J., Bartsch, H. Cancer Res. (1985) [Pubmed]
  2. p53 mutations in primary hepatic angiosarcomas not associated with vinyl chloride exposure. Soini, Y., Welsh, J.A., Ishak, K.G., Bennett, W.P. Carcinogenesis (1995) [Pubmed]
  3. Mutagenicity and toxicity of chloroethylene oxide and chloroacetaldehyde. Perrard, M.H. Experientia (1985) [Pubmed]
  4. Induction of gene mutations and gene conversions by vinyl chloride metabolites in yeast. Loprieno, N., Barale, R., Baroncelli, S., Bartsch, H., Bronzetti, G., Cammelini, A., Corsi, C., Frezza, D., Nieri, R., Leporini, C., Rosellini, D., Rossi, A.M. Cancer Res. (1977) [Pubmed]
  5. Vinyl chloride-a classical industrial toxicant of new interest. Bolt, H.M. Crit. Rev. Toxicol. (2005) [Pubmed]
  6. Mutagenicity of vinyl chloride and its reactive metabolites, chloroethylene oxide and chloroacetaldehyde, in a metabolically competent human B-lymphoblastoid line. Chiang, S.Y., Swenberg, J.A., Weisman, W.H., Skopek, T.R. Carcinogenesis (1997) [Pubmed]
  7. Mutation induction in Chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2-chloroacetaldehyde. Huberman, E., Bartsch, H., Sachs, L. Int. J. Cancer (1975) [Pubmed]
  8. Quantitative analysis of the DNA adduct N2,3-ethenoguanine using liquid chromatography/electrospray ionization mass spectrometry. Yen, T.Y., Christova-Gueoguieva, N.I., Scheller, N., Holt, S., Swenberg, J.A., Charles, M.J. Journal of mass spectrometry : JMS. (1996) [Pubmed]
  9. Induction of specific base-pair substitutions in E. coli trpA mutants by chloroethylene oxide, a carcinogenic vinyl chloride metabolite. Barbin, A., Besson, F., Perrard, M.H., Béréziat, J.C., Kaldor, J., Michel, G., Bartsch, H. Mutat. Res. (1985) [Pubmed]
  10. Metabolism of genotoxic agents: halogenated compounds. Bolt, H.M. IARC Sci. Publ. (1984) [Pubmed]
  11. New adducts of chloroethylene oxide and chloroacetaldehyde with pyrimidine nucleosides. Barbin, A., Friesen, M., O'Neill, I.K., Croisy, A., Bartsch, H. Chem. Biol. Interact. (1986) [Pubmed]
  12. The GST T1 and CYP2E1 genotypes are possible factors causing vinyl chloride induced abnormal liver function. Huang, C.Y., Huang, K.L., Cheng, T.J., Wang, J.D., Hsieh, L.L. Arch. Toxicol. (1997) [Pubmed]
  13. recA-independent mutagenicity induced by chloroethylene oxide in E. coli. Barbin, A., Tenenbaum, L., Toman, Z., Radman, M., Bartsch, H. Mutat. Res. (1985) [Pubmed]
  14. Detection of 1,N6-ethenoadenine in rat urine after chloroethylene oxide exposure. Holt, S., Yen, T.Y., Sangaiah, R., Swenberg, J.A. Carcinogenesis (1998) [Pubmed]
  15. Analysis of 1,N2-ethenoguanine and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine in DNA treated with 2-chlorooxirane by high performance liquid chromatography/electrospray mass spectrometry and comparison of amounts to other DNA adducts. Müller, M., Belas, F.J., Blair, I.A., Guengerich, F.P. Chem. Res. Toxicol. (1997) [Pubmed]
  16. The effect of vinyl chloride monomer, chloroethylene oxide and chloracetaldehyde on DNA synthesis in regenerating rat liver. Border, E.A., Webster, I. Chem. Biol. Interact. (1977) [Pubmed]
  17. High prevalence of K-ras-2 mutations in hepatocellular carcinomas in workers exposed to vinyl chloride. Weihrauch, M., Benick, M., Lehner, G., Wittekind, M., Bader, M., Wrbitzk, R., Tannapfel, A. International archives of occupational and environmental health. (2001) [Pubmed]
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