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Chemical Compound Review

Clarosan     N'-ethyl-6-methylsulfanyl-N- tert-butyl-1,3...

Synonyms: Prebane, Shortstop, Terbutrex, Terbutryn, Saterb, ...
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Disease relevance of Clarosan

  • Several mutants of the purple bacterium Rhodopseudomonas viridis resistant to terbutryn [2-(methylthio)-4-(ethylamino)-6-(tert-butylamino)-s-triazine] have been isolated by their ability to grow photosynthetically in the presence of the herbicide [1].
  • Inhibition of Staphylococcus aureus by free iodine dosages of 0.25, 0.5, 0.75, and 1.0 mg/liter was unaffected by the presence of 2.0 mg of terbutryne per liter [2].
  • However, the effects on L. variegatus were an indirect effect of terbutryn as a consequence of decrease in the aufwuchs food source and occurred at three-orders-of-magnitude-lower concentrations of terbutryn than the acute toxicity effects [3].
  • The uptake of the triazine herbicides, atrazine and terbutryn, was determined for two freshwater photosynthetic microorganisms, the green microalga Chlorella vulgaris and the cyanobacterium Synechococcus elongatus [4].

High impact information on Clarosan

  • It has been established by X-ray crystallography that the triazine herbicide terbutryn binds to the QB site [5].
  • The results obtained by the combination of these different techniques are discussed with respect to the three-dimensional structure of the wild type and the mode of binding of ubiquinone, terbutryn, and o-phenanthroline as determined by X-ray structure analysis [1].
  • Finally, purified recombinant FMO3, the major FMO in human liver, exhibited no significant activity (< 0.1 nmol (nmol of FMO3)-1 min-1) in the formation of the parent sulfoxides of ametryne and terbutryne [6].
  • Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes [6].
  • Electron transport in reaction centers prepared from one of the mutants (M6) was neither inhibited by PPCTH and other NH-thiazoles nor terbutryn [7].

Biological context of Clarosan


Anatomical context of Clarosan

  • Sixteen metabolites of terbutryn were isolated from the urine and feces of either rats or a goat given single oral doses of terbutryn-[14C](2-(t-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine) [12].
  • K1F4 is a hybridoma secreting monoclonal (IgG) antibody reactive to terbutryn and prometryn, two members of the triazine family [13].
  • 5. The amplitudes of chemically evoked contractions in "skinned muscle cells" of Helix PRM or Lumbricus segments were influenced neither by CIPC nor by terbutryn [14].

Associations of Clarosan with other chemical compounds


Gene context of Clarosan

  • The CYP1A2-dependent metabolism of the triazine derivatives ametryne and terbutryne was moderately enhanced by increased CYPOR activity [11].
  • Except MAV 3 all Rps. viridis mutants are different from those selected by their resistance towards the closely related triazine terbutryn [18].

Analytical, diagnostic and therapeutic context of Clarosan


  1. Characterization of four herbicide-resistant mutants of Rhodopseudomonas viridis by genetic analysis, electron paramagnetic resonance, and optical spectroscopy. Sinning, I., Michel, H., Mathis, P., Rutherford, A.W. Biochemistry (1989) [Pubmed]
  2. Antialgal substances for iodine-disinfected swimming pools. Nilson, E.L., Unz, R.F. Appl. Environ. Microbiol. (1977) [Pubmed]
  3. Effects of terbutryn on aufwuchs and Lumbriculus variegatus in artificial indoor streams. Brust, K., Licht, O., Hultsch, V., Jungmann, D., Nagel, R. Environ. Toxicol. Chem. (2001) [Pubmed]
  4. Removal of triazine herbicides from freshwater systems using photosynthetic microorganisms. González-Barreiro, O., Rioboo, C., Herrero, C., Cid, A. Environ. Pollut. (2006) [Pubmed]
  5. Refined crystal structures of reaction centres from Rhodopseudomonas viridis in complexes with the herbicide atrazine and two chiral atrazine derivatives also lead to a new model of the bound carotenoid. Lancaster, C.R., Michel, H. J. Mol. Biol. (1999) [Pubmed]
  6. Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes. Lang, D.H., Rettie, A.E., Böcker, R.H. Chem. Res. Toxicol. (1997) [Pubmed]
  7. A single mutation in the M-subunit of Rhodospirillum rubrum confers herbicide resistance. Sopp, G., Rutherford, W.A., Oettmeier, W. FEBS Lett. (1997) [Pubmed]
  8. Gene transfer system for Rhodopseudomonas viridis. Lang, F.S., Oesterhelt, D. J. Bacteriol. (1989) [Pubmed]
  9. A new mutation in the pufL gene responsible for the terbutryn resistance phenotype in Rubrivivax gelatinosus. Ouchane, S., Picaud, M., Astier, C. FEBS Lett. (1995) [Pubmed]
  10. Herbicide-quinone competition in the acceptor complex of photosynthetic reaction centers from Rhodopseudomonas sphaeroides: a bacterial model for PS-II-herbicide activity in plants. Stein, R.R., Castellvi, A.L., Bogacz, J.P., Wraight, C.A. J. Cell. Biochem. (1984) [Pubmed]
  11. Stable expression and coexpression of human cytochrome P450 oxidoreductase and cytochrome P450 1A2 in V79 Chinese hamster cells: sensitivity to quinones and biotransformation of 7-alkoxyresorufins and triazines. Schmalix, W.A., Lang, D., Schneider, A., Bocker, R., Greim, H., Doehmer, J. Drug Metab. Dispos. (1996) [Pubmed]
  12. Metabolism of [14C] terbutryn (2-(t-butylamino)-4-(ethylamino)-6-(methylthio-s-triazine) by rats and goat. Larsen, G.L., Bakke, J.E., Feil, V.J. Biomed. Mass Spectrom. (1978) [Pubmed]
  13. Nucleotide sequence of the variable region of the heavy and light chains of a monoclonal IgG antibody reactive to herbicides, terbutryn and prometryn. Kreissig, S.B., Ward, V.K., Hammock, B.D., Choudary, P.V. DNA Seq. (1995) [Pubmed]
  14. Evidence that herbicides relaxing smooth and oblique-striated muscles affect the muscle cell membrane. Schwippert, W.W., Beneke, T.W. Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. (1987) [Pubmed]
  15. Genotoxicity testing of five herbicides in the Drosophila wing spot test. Kaya, B., Yanikoglu, A., Creus, A., Marcos, R. Mutat. Res. (2000) [Pubmed]
  16. In vitro genotoxicity of terbutryn evaluated by the alkaline single-cell microgel-electrophoresis "comet" assay. Villarini, M., Scassellati-Sforzolini, G., Moretti, M., Pasquini, R. Cell Biol. Toxicol. (2000) [Pubmed]
  17. Physiological response of freshwater microalga (Chlorella vulgaris) to triazine and phenylurea herbicides. Rioboo, C., González, O., Herrero, C., Cid, A. Aquat. Toxicol. (2002) [Pubmed]
  18. Sequence analysis of four atrazine-resistant mutants from Rhodopseudomonas viridis. Ewald, G., Wiessner, C., Michel, H. Z. Naturforsch., C, J. Biosci. (1990) [Pubmed]
  19. Two methods for estimating terbutryne residues in water using high-pressure liquid chromatography and gas-liquid chromatography with a conductivity detector. Byast, T.H., Cotterill, E.G. J. Chromatogr. (1975) [Pubmed]
  20. Bioconcentration, biomagnification and metabolism of (14)C-terbutryn and (14)C-benzo[a]pyrene in Gammarus fossarum and Asellus aquaticus. Richter, S., Nagel, R. Chemosphere (2007) [Pubmed]
  21. An immunoassay for terbutryn using direct hapten linkage to a glutaraldehyde network on the polystyrene surface of standard microtiter plates. Holthues, H., Pfeifer-Fukumura, U., Hartmann, I., Baumann, W. Fresenius' journal of analytical chemistry. (2001) [Pubmed]
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