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Chemical Compound Review

zlchem 428     5-chloro-1H-pyrimidine-2,4- dione

Synonyms: PubChem14138, SureCN42227, SureCN67366, CHEMBL144082, AG-C-92270, ...
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Disease relevance of NSC 28172


High impact information on NSC 28172


Biological context of NSC 28172


Anatomical context of NSC 28172


Associations of NSC 28172 with other chemical compounds

  • Because 5-chlorouracil and 5-bromouracil can be incorporated into nuclear DNA, and these thymine analogs are well known mutagens, our observations raise the possibility that halogenation reactions initiated by phagocytes provide one pathway for mutagenesis and cytotoxicity at sites of inflammation [4].

Gene context of NSC 28172

  • Cytidine deaminase from mouse kidney converted CDC into CDU; thymidine phosphorylase converted CDU into 5-chlorouracil (5-CU) [9].
  • Introduction of an N-substituted aminomethyl side chain at the 6-position of 5-chlorouracil has improved water solubility and enhanced inhibitory activity compared with the known TP inhibitor, 6-amino-5-chlorouracil [10].
  • The space group is P21/c, with a equals 8.450(6), b equals 6.842(3), c equals 11.072(16) angstrom, beta equals 123.53(19) degrees for 5-chlorouracil, and a equals 8.598(3), b equals 6.886(1), c equals 11.417(5) angstrom, beta equals 123.93(3) degrees for 5-bromouracil [11].

Analytical, diagnostic and therapeutic context of NSC 28172

  • Retrodialysis calibration using 5-chlorouracil (5-CU) was performed in conjunction with on-line HPLC analysis [12].


  1. Myeloperoxidase generates 5-chlorouracil in human atherosclerotic tissue: a potential pathway for somatic mutagenesis by macrophages. Takeshita, J., Byun, J., Nhan, T.Q., Pritchard, D.K., Pennathur, S., Schwartz, S.M., Chait, A., Heinecke, J.W. J. Biol. Chem. (2006) [Pubmed]
  2. Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides. Van Aerschot, A., Everaert, D., Balzarini, J., Augustyns, K., Jie, L., Janssen, G., Peeters, O., Blaton, N., De Ranter, C., De Clercq, E. J. Med. Chem. (1990) [Pubmed]
  3. Stereospecific synthesis and antiviral activities of beta-L-2',3'-dideoxy-5-chloropyrimidine nucleoside derivatives. Pierra, C., Gosselin, G., Sommadossi, J.P., Faraj, A., De Clercq, E., Balzarini, J., Imbach, J.L. Nucleosides Nucleotides (1999) [Pubmed]
  4. Phagocytes produce 5-chlorouracil and 5-bromouracil, two mutagenic products of myeloperoxidase, in human inflammatory tissue. Henderson, J.P., Byun, J., Takeshita, J., Heinecke, J.W. J. Biol. Chem. (2003) [Pubmed]
  5. 5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. A gas chromatography-mass spectrometry assay. Jiang, Q., Blount, B.C., Ames, B.N. J. Biol. Chem. (2003) [Pubmed]
  6. Synthesis and characterization of oligonucleotides containing 5-chlorocytosine. Kang, J.I., Burdzy, A., Liu, P., Sowers, L.C. Chem. Res. Toxicol. (2004) [Pubmed]
  7. The genetic toxicology of 5-fluoropyrimidines and 5-chlorouracil. Morris, S.M. Mutat. Res. (1993) [Pubmed]
  8. Environmental pollutant 5-chlorouracil is incorporated in mouse liver and testes DNA. Pal, B.C., Cumming, R.B., Walton, M.F., Preston, R.J. Mutat. Res. (1981) [Pubmed]
  9. Analytical and pharmacokinetic studies with 5-chloro-2'-deoxycytidine. Hale, J.T., Bigelow, J.C., Mathews, L.A., McCormack, J.J. Biochem. Pharmacol. (2002) [Pubmed]
  10. Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: discovery of novel orally active inhibitors of human thymidine phosphorylase. Yano, S., Kazuno, H., Suzuki, N., Emura, T., Wierzba, K., Yamashita, J., Tada, Y., Yamada, Y., Fukushima, M., Asao, T. Bioorg. Med. Chem. (2004) [Pubmed]
  11. Relationship between the mutagenic and base-stacking properties of halogenated uracil derivatives. The crystal structures of 5-chloro- and 5-bromouracil. Sternglanz, H., Bugg, C.E. Biochim. Biophys. Acta (1975) [Pubmed]
  12. Measurement of drug release from microcarriers by microdialysis. Hitzman, C.J., Wiedmann, T.S., Dai, H., Elmquist, W.F. Journal of pharmaceutical sciences. (2005) [Pubmed]
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