In vitro metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in rats, pigs, and humans

Drug Metabolism and Disposition

Volumn 24, Issue 8, 1996, Pages 859-865

  Lang, Dieter ^a   Criegee, Dagmar ^a   Grothusen, Anja ^a   Saalfrank, Rolf W ^a   Böcker, Ronald H ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMETRYN; ATRAZINE; HERBICIDE; TRIAZINE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CHIRALITY; DEALKYLATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYDROXYLATION; LIVER MICROSOME; MASS SPECTROMETRY; METABOLISM; METABOLITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY; SWINE;

ANIMALS; ATRAZINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HERBICIDES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; RATS; SPECIES SPECIFICITY; SPECTROPHOTOMETRY, ULTRAVIOLET; SWINE; TRIAZINES;

ANIMALIA; SUS SCROFA;

EID: 0029813484     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. J. M. Erickson, M. Rahire, J.-D. Rochaix, and L. Mets: Herbicide resistance and crossresistance: changes at three distinct sites in the herbicide binding protein. Science (Wash. DC) 228, 204-207 (1985).
2. IARC: atrazine: IARC Monogr. Eval. Carcinog. Risk Hum. 53, 441-466 (1991).
3. B. Gath, W. Jaeschke, R. Kubiak, I. Ricker, F. Schmider, and E. Zietz: Depositionsmonitoring von Pflanzenschutzmitteln: Teil 2 Süddeutscher Raum. Nachrichtenbl. Dtsch. Pflanzenschutzdienst (Bert.) 45, 134-143 (1993).
4. J. T. Stevens and D. D. Summer: Herbicides. In "Handbook of Pesticide Toxicology" (W. J. Hayes and E. R. Laws, Jr., eds.), pp. 1381-1389. Academic Press, New York, 1991.
5. D. E. Bradway and R. F. Moseman: Determination of urinary residue levels of N-dealkyl metabolites of triazine herbicides. J. Agric. Food Chem. 30, 244-247 (1982).
6. M. D. Erickson, C. W. Frank, and D. P. Morgan: Determination of s-triazine herbicide residue in urine: studies of excretion and metabolism in swine as a model to human metabolism. J. Agric. Food Chem. 27, 743-745 (1979).
7. W. H. Oliver, G. S. Born, and P. L. Ziemer: Retention, distribution, and excretion of ametryne (2-methylmercapto-4-ethylamino-6-isopropylamino-s-triazine) in the rat. J. Agric. Food Chem. 17, 1207-1209 (1969).
8. J. E. Bakke, J. D. Larson, and C. E. Price: Metabolism of atrazine and 2-hydroxyatrazine in rat. J. Agric. Food Chem. 20, 602-607 (1972).
9. W. C. Dauterman and W. Muecke: In vitro metabolism of atrazine by rat liver. Pestic. Biochem. Physiol. 4, 212-219 (1974).
10. N. H. Adams, P. E. Levi, and E. Hodgson: In vitro studies of the metabolism of atrazine, simazine and terbutryne of several vertebrate species. J. Agric. Food Chem. 38, 1411-1417 (1990).
11. F. Catenacci, F. Barbieri, M. Bersani, A. Ferioli, D. Cottica, and M. Maroni: Biological monitoring of human exposure to atrazine. Toxicol. Lett. 69, 217-222 (1993).
12. R. Ikonen, J. Kangas, and H. Savolainen: Urinary metabolites as indicators for human exposure to atrazine. Toxicol. Lett. 44, 109-112 (1988).
13. A. D. Lucas, A. D. Jones, M. H. Goodrow, S. G. Saiz, C. Blewett, J. N. Seiber, and B. D. Hammock: Determination of atrazine metabolites in human urine: development of a biomarker of exposure. Chem. Res. Toxicol. 6, 107-116 (1993).
14. F. P. Guengerich: Analysis and characterization of enzymes. In "Principles and Methods of Toxicology" (A. W. Hayes, ed.), pp. 777-814. Raven Press, New York, 1989.
15. T. Omura and R. Sato: The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2379-2385 (1964).
16. M. M. Bradford: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254 (1976).
17. E. J. Corey and A. Venkateswarlu: Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J. Am. Chem. Soc. 94, 6190-6191 (1972).
18. T. P. Mawkinney and M. A. Madson: N-Methyl-N-(tert-butyldimethylsilyl)trifluoro-acetamide and related N-tert-butyl dimethylsilyl-amides as protective silyl donors. J. Org. Chem. 47, 3336-3339 (1982).
19. S. Masaphy, D. Levanon, J. Vaya, and Y. Henis: Isolation and characterization of a novel atrazine metabolite produced by the fungus Pleurotus pulmonatius,2-chloro-4-ethylamino-6-(1-hydroxyisopropyl)-amino-1,3,5-triazine. Appl. Environ. Microbiol. 59, 4342-4346 (1993).
20. 14C]terbutryne [2-(t-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine] by rats and goat. Biomed. Mass Spectrom. 5, 382-390 (1978).
21. G. L. Larsen and J. E. Bakke: Mass spectral characterization of the glucuronide conjugates of terbutryne [2-(t-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine] metabolites from rats and goat. Biomed. Mass Spectrom. 5, 391-394 (1978).
22. D. J. Brusick: An assessment of the genetic toxicity of atrazine: relevance to human health and environmental effects. Mutation Res. 317, 133-144 (1994).
23. F. P. Guengerich, O. Okazaki, Y. Seto, and T. L. Macdonald: Radical cation intermediates in N-dealkylation reactions. Xenobiotica 25, 689-709 (1995).
24. F. P. Guengerich: Enzymatic oxidation of xenobiotic chemicals. Crit. Rev. Biochem. Mol. Biol. 25, 97-153 (1990).
25. A. R. Katritzky, C. W. Rees, and J. M. E. Quirke: 1,3,5, Triazines. "Comprehensive Heterocyclic Chemistry," p. 457-530. Pergamon Press, New York, 1984.
26. H. O. Esser, G. Dupuis, E. Ebert, G. J. Marco, and C. Vogel: s-Triazines. In "Herbicides: Chemistry, Degradation and Mode of Action" (P. C. Kearny and D. D. Kaufmann, eds.), 129-208. Marcel Dekker Inc., New York, 1976.
27. D. Lang and R. Böcker: Species specific metabolism of various s-triazines to investigate mechanisms and characteristics of cytochrome P-450 catalyzed reactions. ISSX Proc. 8, 185 (1995).