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Chemical Compound Review

p-CA     4-chloroaniline

Synonyms: p-Chloraniline, PubChem16666, CCRIS 131, CHEMBL15888, SureCN27544, ...
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Disease relevance of para-Chloroaniline

  • A series of sulfonimidamide analogs of the oncolytic diarylsulfonylureas was synthesized and evaluated for (1) in vitro cytotoxicity against CEM cells, (2) in vivo antitumor activity against subaxillary implanted 6C3HED lymphosarcoma, and (3) metabolic breakdown to the o-sulfate of p-chloroaniline [1].
  • The metabolic formation of p-chloroaniline from the oncolytic agent sulofenur [N-(5-indanesulfonyl)-N'-(4-chlorophenyl)urea, LY186641,] and from similar diaryl-substituted sulfonylureas, and its possible relevance to the compound's toxicity, was studied [2].
  • Metabolic formation of p-chloroaniline thus appears to be a plausible explanation for the methemoglobinemia and anemia found to be dose-limiting toxicities of sulofenur in Phase I trials [2].
  • A major goal of these studies was to determine whether p-chloroaniline is formed in significant quantities during the course of sulofenur metabolism. p-Chloroaniline, capable of being formed by hydrolysis of this diarylsulfonylurea, is known to induce methemoglobinemia and/or hemolytic anemia [3].
  • 4-Chloroaniline was metabolized in a liquid growth medium by a Streptomyces sp. which was isolated from soil [4].

High impact information on para-Chloroaniline


Chemical compound and disease context of para-Chloroaniline


Biological context of para-Chloroaniline

  • Populations of Tn5271-carrying bacteria were significantly higher in microcosms dosed with 3-chlorobenzoate, 4-chloroaniline, and 3-chlorobiphenyl than in the control microcosms, indicating that each of these chemicals exerts a selective force on this particular genotype in natural systems [7].
  • The toxicokinetics and in vivo metabolism of both aniline and 4-chloroaniline were best described by a two-compartment model that was consistent with the assumption that metabolites of the parent amines were accumulating in the fish [9].
  • Based on an analysis of excreted metabolites, N-acetylation was the dominant route of in vivo metabolism for 4-chloroaniline, with no indication of ring hydroxylation, while the evidence suggested that polar conjugates were the dominant in vivo aniline metabolites [9].
  • Stopped-flow spectrophotometric studies on the influence of cytochrome b5 on the kinetics of binding to cytochrome P-450 of 4-chloroaniline and/or cumene hydroperoxide show that the rates of formation and decay of the adducts change as the molar ratio of cytochrome b5 to cytochrome P-450 varies [10].
  • 2. Dependence of biotransformation on aqueous concentration was investigated with 4CA [11].

Anatomical context of para-Chloroaniline


Associations of para-Chloroaniline with other chemical compounds


Analytical, diagnostic and therapeutic context of para-Chloroaniline


  1. Sulfonimidamide analogs of oncolytic sulfonylureas. Toth, J.E., Grindey, G.B., Ehlhardt, W.J., Ray, J.E., Boder, G.B., Bewley, J.R., Klingerman, K.K., Gates, S.B., Rinzel, S.M., Schultz, R.M., Weir, L.C., Worzalla, J.F. J. Med. Chem. (1997) [Pubmed]
  2. Comparison of metabolism and toxicity to the structure of the anticancer agent sulofenur and related sulfonylureas. Ehlhardt, W.J., Woodland, J.M., Worzalla, J.F., Bewley, J.R., Grindey, G.B., Todd, G.C., Toth, J.E., Howbert, J.J. Chem. Res. Toxicol. (1992) [Pubmed]
  3. Metabolism and disposition of the anticancer agent sulofenur in mouse, rat, monkey, and human. Ehlhardt, W.J. Drug Metab. Dispos. (1991) [Pubmed]
  4. Formylation and acetylation of 4-chloroaniline by a Streptomyces sp. Russel, S., Bollag, J.M. Acta Microbiol. Pol. (1977) [Pubmed]
  5. The role of lipid peroxidation in the N-oxidation of 4-chloroaniline. Golly, I., Hlavica, P., Wolf, J. Biochem. J. (1984) [Pubmed]
  6. The action of chloride peroxidase on 4-chloroaniline. N-oxidation and ring halogenation. Corbett, M.D., Chipko, B.R., Batchelor, A.O. Biochem. J. (1980) [Pubmed]
  7. Involvement of a chlorobenzoate-catabolic transposon, Tn5271, in community adaptation to chlorobiphenyl, chloroaniline, and 2,4-dichlorophenoxyacetic acid in a freshwater ecosystem. Fulthorpe, R.R., Wyndham, R.C. Appl. Environ. Microbiol. (1992) [Pubmed]
  8. Influence of cytochrome P450 mixed-function oxidase induction on the acute toxicity to rainbow trout (Salmo gairdneri) of primary aromatic amines. Hermens, J.L., Bradbury, S.P., Broderius, S.J. Ecotoxicol. Environ. Saf. (1990) [Pubmed]
  9. Toxicokinetics and metabolism of aniline and 4-chloroaniline in medaka (Oryzias latipes). Bradbury, S.P., Dady, J.M., Fitzsimmons, P.N., Voit, M.M., Hammermeister, D.E., Erickson, R.J. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  10. On the function of cytochrome b5 in the cytochrome P-450-dependent oxygenase system. Hlavica, P. Arch. Biochem. Biophys. (1984) [Pubmed]
  11. Biotransformation of monochloroanilines in guppy, Poecilia reticulata. Wang, X.Q., Seinen, W., De Wolf, W. Xenobiotica (1994) [Pubmed]
  12. Metabolic activation and nucleic acid binding of acetaminophen and related arylamine substrates by the respiratory burst of human granulocytes. Corbett, M.D., Corbett, B.R., Hannothiaux, M.H., Quintana, S.J. Chem. Res. Toxicol. (1989) [Pubmed]
  13. N-demethylation of p-chloro-N-methylaniline catalyzed by subcellular fractions from the avocado pear (Persea americana). Dohn, D.R., Krieger, R.I. Arch. Biochem. Biophys. (1984) [Pubmed]
  14. Toxicity of 4-chloroaniline in early life stages of zebrafish (Danio rerio): II. Cytopathology and regeneration of liver and gills after prolonged exposure to waterborne 4-chloroaniline. Burkhardt-Holm, P., Oulmi, Y., Schroeder, A., Storch, V., Braunbeck, T. Arch. Environ. Contam. Toxicol. (1999) [Pubmed]
  15. Tissue distribution, subcellular localization and covalent binding of 2-chloroaniline and 4-chloroaniline in Fischer 344 rats. Dial, L.D., Anestis, D.K., Kennedy, S.R., Rankin, G.O. Toxicology (1998) [Pubmed]
  16. HPLC determination of chlorhexidine gluconate and p-chloroaniline in topical ointment. Havlíková, L., Matysová, L., Nováková, L., Hájková, R., Solich, P. Journal of pharmaceutical and biomedical analysis (2007) [Pubmed]
  17. Estimation of kinetic rate constants for biodegradation of chemicals in activated sludge wastewater treatment plants using short term batch experiments and microgram/L range spiked concentrations. Nyholm, N., Ingerslev, F., Berg, U.T., Pedersen, J.P., Frimer-Larsen, H. Chemosphere (1996) [Pubmed]
  18. Toxicity of 4-chloroaniline in early life-stages of zebrafish (Brachydanio rerio): I. cytopathology of liver and kidney after microinjection. Oulmi, Y., Braunbeck, T. Arch. Environ. Contam. Toxicol. (1996) [Pubmed]
  19. Gas chromatographic determination of p-chloroaniline in a chlorhexidine digluconate-containing alcohol foam surgical scrub product. Gavlick, W.K., Davis, P.K. Journal of AOAC International. (1994) [Pubmed]
  20. In vivo study of percutaneous absorption of 4-chloroaniline using microdialysis in the rat. el Marbouh, L., Arellano, C., Philibert, C., Evrard, P., Poëy, J., Houin, G. Arzneimittel-Forschung. (2000) [Pubmed]
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