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Chemical Compound Review

pentachlorophenol     2,3,4,5,6-pentachlorophenol

Synonyms: Fungifen, Liroprem, Pentacon, Permasan, Permatox, ...
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Disease relevance of pentachlorophenol


High impact information on pentachlorophenol


Chemical compound and disease context of pentachlorophenol


Biological context of pentachlorophenol


Anatomical context of pentachlorophenol


Associations of pentachlorophenol with other chemical compounds


Gene context of pentachlorophenol

  • The tested products fell into four major groups: a first group with pentachlorophenol, identified as a CYP3A inducer; a second group containing the methylcholanthrene-type inducers that increase CYP1A-related activities; a third class represented by dieldrin, a PB-type inducer; a fourth group including inert compounds or weak inducers [27].
  • Neuregulin 1-Beta Cytoprotective Role in AML 12 Mouse Hepatocytes Exposed to Pentachlorophenol [28].
  • CYP1a1, HSP70, P53, and c-fos expression in human liver carcinoma cells (HepG2) exposed to pentachlorophenol [29].
  • Hexachlorocyclohexane reduced [3H]5 alpha-DHT binding to hSHBG by 20%, but the stereospecific effects observed with ABP did not occur. o,p'-DDT and pentachlorophenol resulted in a statistically significant 20% inhibition of [3H]5 alpha-DHT binding to hSHBG [30].
  • Human lymphocyte reactivity after in vitro exposure to technical and analytical grade pentachlorophenol [31].

Analytical, diagnostic and therapeutic context of pentachlorophenol


  1. Aplastic anemia due to pentachlorophenol. Roberts, H.J. N. Engl. J. Med. (1981) [Pubmed]
  2. Urticaria from contact with pentachlorophenate. Kentor, P.M. JAMA (1986) [Pubmed]
  3. Evolution of a metabolic pathway for degradation of a toxic xenobiotic: the patchwork approach. Copley, S.D. Trends Biochem. Sci. (2000) [Pubmed]
  4. Pentachlorophenol pancreatitis. Cooper, R.G., Macauley, M.B. Lancet (1982) [Pubmed]
  5. Structural and biochemical characterization of a quinol binding site of Escherichia coli nitrate reductase A. Bertero, M.G., Rothery, R.A., Boroumand, N., Palak, M., Blasco, F., Ginet, N., Weiner, J.H., Strynadka, N.C. J. Biol. Chem. (2005) [Pubmed]
  6. Exposure to phenoxyacetic acids, chlorophenols, or organic solvents in relation to histopathology, stage, and anatomical localization of non-Hodgkin's lymphoma. Hardell, L., Eriksson, M., Degerman, A. Cancer Res. (1994) [Pubmed]
  7. Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: an ESR spin trapping study. Zhu, B.Z., Zhao, H.T., Kalyanaraman, B., Frei, B. Free Radic. Biol. Med. (2002) [Pubmed]
  8. pH homeostasis in promyelocytic leukemic HL60 cells. Restrepo, D., Kozody, D.J., Spinelli, L.J., Knauf, P.A. J. Gen. Physiol. (1988) [Pubmed]
  9. Human sulphotransferases are involved in the activation of aristolochic acids and are expressed in renal target tissue. Meinl, W., Pabel, U., Osterloh-Quiroz, M., Hengstler, J.G., Glatt, H. Int. J. Cancer (2006) [Pubmed]
  10. Exploration of the relationship between tetrachlorohydroquinone dehalogenase and the glutathione S-transferase superfamily. McCarthy, D.L., Navarrete, S., Willett, W.S., Babbitt, P.C., Copley, S.D. Biochemistry (1996) [Pubmed]
  11. Evidence that pcpA encodes 2,6-dichlorohydroquinone dioxygenase, the ring cleavage enzyme required for pentachlorophenol degradation in Sphingomonas chlorophenolica strain ATCC 39723. Xu, L., Resing, K., Lawson, S.L., Babbitt, P.C., Copley, S.D. Biochemistry (1999) [Pubmed]
  12. N-sulfoöxy-2-aminofluorene is the major ultimate electrophilic and carcinogenic metabolite of N-hydroxy-2-acetylaminofluorene in the livers of infant male C57BL/6J x C3H/HeJ F1 (B6C3F1) mice. Lai, C.C., Miller, J.A., Miller, E.C., Liem, A. Carcinogenesis (1985) [Pubmed]
  13. Impact of the specificity of the exposure metric on exposure-response relationships. Friesen, M.C., Davies, H.W., Teschke, K., Ostry, A.S., Hertzman, C., Demers, P.A. Epidemiology (Cambridge, Mass.) (2007) [Pubmed]
  14. Strong intensification of mouse hepatic tamoxifen DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol. Randerath, K., Bi, J., Mabon, N., Sriram, P., Moorthy, B. Carcinogenesis (1994) [Pubmed]
  15. Induction of direct adducts, apurinic/apyrimidinic sites and oxidized bases in nuclear DNA of human HeLa S3 tumor cells by tetrachlorohydroquinone. Lin, P.H., Nakamura, J., Yamaguchi, S., La, D.K., Upton, P.B., Swenberg, J.A. Carcinogenesis (2001) [Pubmed]
  16. Inhibition of bacterial transport by uncouplers of oxidative phosphorylation. Effects of pentachlorophenol and analogues in Bacillus subtilis. Nicholas, R.A., Ordal, G.W. Biochem. J. (1978) [Pubmed]
  17. Prevention of the down-regulation of gap junctional intercellular communication by green tea in the liver of mice fed pentachlorophenol. Sai, K., Kanno, J., Hasegawa, R., Trosko, J.E., Inoue, T. Carcinogenesis (2000) [Pubmed]
  18. Oscillations of nitric oxide concentration in the perturbed denitrification pathway of Paracoccus denitrificans. Kucera, I. Biochem. J. (1992) [Pubmed]
  19. Electrical conductivity in lipid bilayer membranes induced by pentachlorophenol. Smejtek, P., Hsu, K., Perman, W.H. Biophys. J. (1976) [Pubmed]
  20. Oxidative damage and direct adducts in calf thymus DNA induced by the pentachlorophenol metabolites, tetrachlorohydroquinone and tetrachloro-1,4-benzoquinone. Lin, P.H., Nakamura, J., Yamaguchi, S., Upton, P.B., La, D.K., Swenberg, J.A. Carcinogenesis (2001) [Pubmed]
  21. Effect of pentachlorophenol on calcium accumulation in barnacle muscle cells. Nwoga, J.C., Sniffen, J.C., Peña-Rasgado, C., Kimler, V.A., Rasgado-Flores, H. J. Physiol. (Lond.) (1996) [Pubmed]
  22. Highly cooperative inhibition of acetylcholinesterase by pentachlorophenol in human erythrocytes. Igisu, H., Hamasaki, N., Ikeda, M. Biochem. Pharmacol. (1993) [Pubmed]
  23. 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice. Randerath, K., Haglund, R.E., Phillips, D.H., Reddy, M.V. Carcinogenesis (1984) [Pubmed]
  24. Prevention of dual promoting effects of pentachlorophenol, an environmental pollutant, on diethylnitrosamine-induced hepato- and cholangiocarcinogenesis in mice by green tea infusion. Umemura, T., Kai, S., Hasegawa, R., Kanki, K., Kitamura, Y., Nishikawa, A., Hirose, M. Carcinogenesis (2003) [Pubmed]
  25. Excretion of hexachlorobenzene and metabolites in feces in a highly exposed human population. To-Figueras, J., Barrot, C., Sala, M., Otero, R., Silva, M., Ozalla, M.D., Herrero, C., Corbella, J., Grimalt, J., Sunyer, J. Environ. Health Perspect. (2000) [Pubmed]
  26. Influence of the consumption of fatty Baltic Sea fish on plasma levels of halogenated environmental contaminants in Latvian and Swedish men. Sjödin, A., Hagmar, L., Klasson-Wehler, E., Björk, J., Bergman, A. Environ. Health Perspect. (2000) [Pubmed]
  27. Hierarchical cluster analysis of environmental pollutants through P450 induction in cultured hepatic cells. Dubois, M., Plaisance, H., Thomé, J.P., Kremers, P. Ecotoxicol. Environ. Saf. (1996) [Pubmed]
  28. Neuregulin 1-Beta Cytoprotective Role in AML 12 Mouse Hepatocytes Exposed to Pentachlorophenol. Dorsey, W.C., Tchounwou, P.B., Ford, B.D. International journal of environmental research and public health [electronic resource]. (2006) [Pubmed]
  29. CYP1a1, HSP70, P53, and c-fos expression in human liver carcinoma cells (HepG2) exposed to pentachlorophenol. Dorsey, W.C., Tchounwou, P.B. Biomedical sciences instrumentation. (2003) [Pubmed]
  30. Environmental xenobiotics may disrupt normal endocrine function by interfering with the binding of physiological ligands to steroid receptors and binding proteins. Danzo, B.J. Environ. Health Perspect. (1997) [Pubmed]
  31. Human lymphocyte reactivity after in vitro exposure to technical and analytical grade pentachlorophenol. Lang, D., Mueller-Ruchholtz, W. Toxicology (1991) [Pubmed]
  32. Development of rotating electrochemical detectors for capillary electrophoresis. Hilmi, A., Luong, J.H. Anal. Chem. (2001) [Pubmed]
  33. Two trace analytical methods for determination of hydroxylated PCBs and other halogenated phenolic compounds in eggs from Norwegian birds of prey. Berger, U., Herzke, D., Sandanger, T.M. Anal. Chem. (2004) [Pubmed]
  34. Sulfobutylether-beta-cyclodextrin-mediated capillary electrophoresis for separation of chlorinated and substituted phenols. Groom, C.A., Luong, J.H. Electrophoresis (1997) [Pubmed]
  35. Monitoring of Desulfitobacterium frappieri PCP-1 in pentachlorophenol-degrading anaerobic soil slurry reactors. Lanthier, M., Villemur, R., Lépine, F., Bisaillon, J.G., Beaudet, R. Environ. Microbiol. (2000) [Pubmed]
  36. Development of a novel, bioluminescence-based, fungal bioassay for toxicity testing. Weitz, H.J., Campbell, C.D., Killham, K. Environ. Microbiol. (2002) [Pubmed]
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