Pyrethroids: Mammalian metabolism and toxicity

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 7, 2011, Pages 2786-2791

  Kaneko, Hideo ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLESTERASES; CHIRAL ISOMERS; ESTER HYDROLYSIS; FENVALERATE; ISOFORMS; MAMMALIAN TOXICITY; METABOLIC FATE; METABOLIC REACTIONS; PYRETHROIDS; RESEARCH GROUPS; SUMITOMO CHEMICALS; SYNTHETIC PYRETHROIDS;

ESTERS; ISOMERS; MAMMALS; PHYSIOLOGY; TOXICITY;

METABOLISM;

CARBOXYLESTERASE; INSECTICIDE; PYRETHROID;

ANIMAL; CONFERENCE PAPER; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION;

ANIMALS; CARBOXYLIC ESTER HYDROLASES; HUMANS; INSECTICIDES; OXIDATION-REDUCTION; PYRETHRINS;

MAMMALIA;

EID: 79953863800     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf102567z     Document Type: Article

References (34)

1. Kaneko, H. Pyrethroid chemistry and metabolism. In Hayes' Handbook of Pesticide Toxicology, 3rd ed.; Krieger, R., Ed.; Elsevier: Amsterdam, The Netherlands, 2010; Chapter 76.
2. Soderlund, D. M. Toxicology and mode of action of pyrethroid Insecticides. In Hayes' Handbook of Pesticide Toxicology, 3rd ed.; Krieger, R., Ed.; Elsevier: Amsterdam, The Netherlands, 2010; Chapter 77.
3. Products section-2008 Market, AgriService, Phillip McDougall, 2009.
4. Ohkawa, H.; Kaneko, H.; Tsuji, H.; Miyamoto, J. Metabolism of fenvalerate (Sumicidin) in rats J. Pestic. Sci. 1979, 4, 143-155
5. Kaneko, H.; Ohkawa, H.; Miyamoto, J. Comparative metabolism of fenvalerate and the [2 S,α S ]-isomer in rats and mice J. Pestic. Sci. 1981, 6, 317-326
6. Ruzo, L. O.; Unai, T.; Casida, J. E. Decamethrin metabolism in rats J. Agric. Food Chem. 1978, 26, 918-924
7. Crawford, M. J.; Croucher, A.; Hutson, D. H. The metabolism of the pyrethroid insecticide cypermethrin in rats: excreted metabolites Pestic. Sci. 1981, 12, 399-411
8. Kaneko, H.; Matsuo, M.; Miyamoto, J. Comparative metabolism of stereoisomers of cyphenothrin and phenothrin isomers in rats J. Pestic. Sci. 1984, 9, 237-247
9. Soderlund, D. M.; Clark, J. M.; Sheets, L. P.; Mullin, L. S.; Piccirillo, V. J.; Sargent, D.; Stevens, J. T.; Weiner, M. L. Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment Toxicology 2002, 171, 3-59 (Pubitemid 34102445)
10. Izumi, T.; Kaneko, H.; Matsuo, M.; Miyamoto, J. Comparative metabolism of the six stereoisomers of phenothrin in rats and mice J. Pestic. Sci. 1984, 9, 259-267
11. Kaneko, H.; Izumi, T.; Ueda, Y.; Matsuo, M.; Miyamoto, J. Metabolism and placental transfer of stereoisomers of tetramethrin isomers in pregnant rats J. Pestic. Sci. 1984, 9, 249-258
12. Gaughan, L. C.; Unai, T.; Casida, J. E. Permethrin metabolism in rats J. Agric. Food Chem. 1977, 25, 9-17 (Pubitemid 8048963)
13. Casida, J. E.; Ruzo, L. O. Metabolic chemistry of pyrethroid insecticides Pestic. Sci. 1980, 11, 257-269
14. Huckle, K. R.; Hutson, D. H.; Millburn, P. Species differences in the metabolism of 3-phenoxybenzoic acid Drug Metab. Dispos. 1981, 9, 352-359 (Pubitemid 11057596)
15. Tomigahara, Y.; Mori, M.; Shiba, K.; Isobe, N.; Kaneko, H.; Nakatsuka, I.; Yamada, H. Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites Xenobiotica 1994, 24, 473-484 (Pubitemid 24170514)
16. Tomigahara, Y.; Shiba, K.; Isobe, N.; Kaneko, H.; Nakatsuka, I.; Yamada, H. Identification of two new types of S-linked conjugates of Etoc in rat Xenobiotica 1994, 24, 839-852 (Pubitemid 24311309)
17. Kaneko, H.; Matsuo, M.; Miyamoto, J. Differential metabolism of fenvalerate and granuloma formation. I. Identification of a cholesterol ester derived from a specific chiral isomer of fenvalerate Toxicol. Appl. Pharmacol. 1986, 83, 148-156 (Pubitemid 16113515)
18. Kaneko, H.; Takamatsu, Y.; Okuno, Y.; Abiko, J.; Yoshitake, A.; Miyamoto, J. Substrate specificity for formation of cholesterol ester conjugates from fenvalerate analogues and for granuloma formation Xenobiotica 1988, 18, 11-19 (Pubitemid 18051816)
19. Moorhouse, K. G.; Logan, C. J.; Hutson, D. H.; Dodds, P. F. The incorporation of 3-phenoxybenzoic acid and other xenobiotics acids into xenobiotic lipids by enzymes of the monoacylglycerol pathway in microsomes from adult and neonatal tissues Biochem. Pharmacol. 1990, 39, 1529-36 (Pubitemid 20157838)
20. Quistad, G. B.; Staiger, L. E.; Schooley, D. A. Xenobiotic conjugation: a novel role for bile acids Nature 1982, 296, 462-464 (Pubitemid 12108534)
21. Okuno, Y.; Seki, T.; Ito, S.; Kaneko, H.; Watanabe, T.; Yamada, H.; Miyamoto, J. Differential metabolism of fenvalerate and granuloma formation. II. Toxicological significance of a lipophilic conjugate from fenvalerate Toxicol. Appl. Pharmacol. 1986, 83, 157-169 (Pubitemid 16113516)
22. Miyamoto, J.; Kaneko, H.; Takamatsu, Y. Stereoselective formation of a cholesterol ester conjugate from fenvalerate by mouse microsomal carboxyesterase(s) J. Biochem. Toxicol. 1986, 1, 79-94
23. Mikata, S.; Takaku, T.; Isobe, N.; Kaneko, H. Unpublished observation.
24. Godin, S. J.; Crow, J. A.; Scollon, E. J.; Hughes, M. F.; DeVito, M. J.; Ross, M. K. Identification of rat and human cytochrome P450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides deltamethrin and esfenvalerate Drug Metab. Dispos. 2007, 35, 1664-1671 (Pubitemid 47296062)
25. Scollon, E. J.; Starr, J. M.; Godin, S. J.; DeVito, M. J.; Hughes, M. F. In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome P450 isoforms Drug Metab. Dispos. 2009, 37, 221-228
26. Leng, G.; Leng, A.; Kuhn, K.-H.; Lewalter, J.; Pauluhn, J. Human dose-excretion studies with the pyrethroid insecticide cyfluthrin: urinary metabolite profile following inhalation Xenobiotica 1997, 27, 1273-1283 (Pubitemid 28060079)
27. Woollen, B. H.; Marsh, J. R.; Laird, W. J. D.; Lesser, J. E. The metabolism of cypermethrin in man: differences in urinary metabolic profiles following oral and dermal administration Xenobiotica 1992, 22, 983-991
28. Capt, A.; Luzy, A. P.; Esdaile, D.; Blanck, O. Comparison of three human skin grafted onto nude mouse model with in vivo and in vitro models in the prediction of percutaneous penetration of three lipophilic pesticides Regul. Toxicol. Pharmacol. 2007, 47, 274-287 (Pubitemid 46420394)
29. Tomalik-Scharte, D.; Lazar, A.; Meins, J.; Bastian, B.; Ihrig, M.; Wachall, B.; Jetter, A.; Tantcheva-Poor, I.; Mahrle, G.; Fuhr, U. Dermal absorption of permethrin following topical administration Eur J. Clin. Pharmacol. 2005, 61, 399-404 (Pubitemid 41569316)
30. Hughes, M. F.; Edwards, B. C. In vitro dermal absorption of pyrethroid pesticides in human and rat skin Toxicol. Appl. Pharmacol. 2010, 246, 29-37
31. Crow, J. A.; Borazjani, A.; Potter, P. M.; Ross, M. K. Hydrolysis of pyrethroids by human and rat tissues: Examination of intestrinal, liverand serum carboxylesterases Toxicol. Appl. Pharmacol. 2007, 221, 1-12 (Pubitemid 46766564)
32. Costa, L. G. Toxic effects of pesticide. In Casarett and Doull's Toxicology, The Basic Science of Poison, 7 th ed.; Klaassen, C. D., Ed.; McGraw Hill: New York, 2007; Chapter 22.
33. Deguchi, Y.; Yamada, T.; Hirose, Y.; Nagahori, H.; Kushida, M.; Sumida, K.; Sukata, T.; Tomigahara, Y.; Nishioka, K.; Uwagawa, S.; Kawamura, S.; Okuno, Y. Mode of action analysis for the synthetic pyrethroid metofluthrin-induced rat liver tumors: evidence for hepatic CYP2B induction and hepatocyte proliferation Toxicol. Sci. 2009, 108, 69-80
34. Toxicological profile for pyrethrins and pyrethroids, U.S. Department of Health and Human Services Public Health Service Agency for Toxic Substances and Disease Registry, 2003.