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Chemical Compound Review

CHEMBL468582     (E)-1,4-dichlorobut-2-ene

Synonyms: CCRIS 2458, CCRIS 8948, AG-D-28144, AG-H-05016, HSDB 1501, ...
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Disease relevance of CCRIS 2458


High impact information on CCRIS 2458


Biological context of CCRIS 2458

  • 1,3-DCB is a by-product of beta-chloroprene from the acetylene route, with 1,4-DCB is an intermediate in the production of beta-chloroprene from the butadiene route, the production route used in the U.S. Presented in the review is a summary of the acute toxicity including mutagen testing, skin, eye, and inhalation testing of these compounds [1].
  • The observed species differences, notably the more pronounced biotransformation of 1,4-DCB to reactive species including benzoquinones, could be factors in this compound's liver carcinogenicity in B6C3F1 mice but not other rodent species [4].
  • Renal cell proliferation, measured by [3H]thymidine incorporation into renal DNA, was increased after 1,4-DCB but not after 1,2-DCB treatment [5].
  • Significant species and sex differences in the oxidation of MCB, 1,2-DCB and 1,4-DCB were reflected in a markedly higher oxidation in male mice than male rats and higher oxidation in male than female mice [6].

Anatomical context of CCRIS 2458

  • Following long-term inhalation (450 and 3000 mg/m3) 1,4-DCB concentrations were highest in adipose tissues at 6 months followed by a marked decline at 18 months [7].
  • Metabolic rates of MCB, 1,2-DCB and 1,4-DCB correlated with CYP2E1 immunochemical level in microsomes from 11 different human livers and with metabolic rates of CYP2E1 substrates [6].

Associations of CCRIS 2458 with other chemical compounds


Gene context of CCRIS 2458

  • The relative roles of human liver CYP2E1 and 3A4 in the metabolism of 1,4-DCB seem to be individually different [6].
  • In contrast to previous studies showing rat CYP3A1 as the main CYP form oxidising both DCBs, our experiments indicate only a certain role of rat and human CYP3A in MCB, 1,2-DCB and 1,4-DCB oxidation to covalently bound products [6].
  • The toxicity produced by 1,4-DCB was suppressed by amino acids, vitamins and 1% BSA [9].

Analytical, diagnostic and therapeutic context of CCRIS 2458

  • Gel filtration chromatography of a 116,000g supernatant prepared from kidneys of 1,4-[14C]DCB-treated rats showed that radiolabel coeluted with alpha 2u-globulin as one sharp peak as opposed to a multipeak pattern observed for 1,2-[14C]DCB; the maximal quantity of radiolabel for 1,4-DCB was twice that for 1,2-DCB [5].
  • 1,4-Dichlorobenzene (1,4-DCB) was shown to induce the formation of male rat renal tubule tumors and male and female mouse liver tumors when administered in a chronic bioassay [10].
  • After single oral administration of 100 and 1000 mg/kg bw and feeding of 100 and 1000 ppm (corresponding to approximately 10 and 100 mg/kg bw) to male Wistar rats for 28 days, the time course of 1,4-DCB and 2,5-DCP concentrations was investigated in plasma, adipose, hepatic and renal tissue [7].


  1. Toxicity of chloroprene, 1,3-dichlorobutene-2, and 1,4-dichlorobutene-2. Clary, J.J. Environ. Health Perspect. (1977) [Pubmed]
  2. Volatile organic compounds and pulmonary function in the Third National Health and Nutrition Examination Survey, 1988-1994. Elliott, L., Longnecker, M.P., Kissling, G.E., London, S.J. Environ. Health Perspect. (2006) [Pubmed]
  3. Investigations on the mutagenicity of 1,4-dichlorobenzene and its main metabolite 2,5-dichlorophenol in vivo and in vitro. Tegethoff, K., Herbold, B.A., Bomhard, E.M. Mutat. Res. (2000) [Pubmed]
  4. Species and strain differences in the hepatic cytochrome P450-mediated biotransformation of 1,4-dichlorobenzene. Hissink, A.M., Oudshoorn, M.J., Van Ommen, B., Van Bladeren, P.J. Toxicol. Appl. Pharmacol. (1997) [Pubmed]
  5. Involvement of reversible binding to alpha 2u-globulin in 1,4-dichlorobenzene-induced nephrotoxicity. Charbonneau, M., Strasser, J., Lock, E.A., Turner, M.J., Swenberg, J.A. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  6. Cytochrome P450 catalyzed oxidation of monochlorobenzene, 1,2- and 1,4-dichlorobenzene in rat, mouse, and human liver microsomes. Nedelcheva, V., Gut, I., Soucek, P., Frantík, E. Chem. Biol. Interact. (1998) [Pubmed]
  7. Time course of enzyme induction in liver and kidneys and absorption, distribution and elimination of 1,4-dichlorobenzene in rats. Bomhard, E.M., Schmidt, U., Löser, E. Toxicology (1998) [Pubmed]
  8. Nasal tumors in rats following long-term inhalation exposure to 1,4-dichlorobutene-2 (DCB). Mullin, L.S., Kennedy, G.L., Wood, C.K. Drug and chemical toxicology. (2000) [Pubmed]
  9. Culture medium composition affects the relative toxicities of chlorobenzenes in rat liver slices and the isolated perfused liver. Fisher, R.L., Gandolfi, A.J., Sipes, I.G., Brendel, K. Drug and chemical toxicology. (1993) [Pubmed]
  10. An evaluation of the carcinogenic hazard of 1,4-dichlorobenzene based on internationally recognized criteria. Barter, J.A., Sherman, J.H. Regulatory toxicology and pharmacology : RTP. (1999) [Pubmed]
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