Metabolism of metofluthrin in rats: I. Identification of metabolites

References

• Abe J, Nagahori H, Omori R, et al. (2015). Metabolism of (Z)-(1R,3R)-profluthrin in Rats. J Agric Food Chem 63:8651–61
   PubMed Web of Science ®Google Scholar
• Bahnson BJ, Anderson VE, Petsko GA. (2002). Structural mechanism of enoyl-CoA hydratase: three atoms from a single water are added in either an E1cb stepwise or concerted fashion. Biochemistry 41:2621–9
   PubMed Web of Science ®Google Scholar
• Baxter JH, Steinberg D, Mize CE, Avigan J. (1967). Absorption and metabolism of uniformly 14C-labeled phytol and phytanic acid by the intestine of the rat studied with thoracic duct cannulation. Biochim Biophys Acta 137:277–90
   PubMedGoogle Scholar
• Bellucci C, Chiappe C, Cordoni A, Marioni F. (1994). Enantioselectivity in the rabbit liver microsomal biotransformation of styrene and phenylpropenes. Biocatalysis 10:149–57
   Web of Science ®Google Scholar
• Casida JE, Quistad GB. (1998). Golden age of insecticide research: past, present, or future?. Annu Rev Entomol 43:1–16
   PubMed Web of Science ®Google Scholar
• Chidgey MA, Kennedy JF, Caldwell J. (1986). Studies on benzyl acetate. II. Use of specific metabolic inhibitors to define the pathway leading to the formation of benzylmercapturic acid in the rat. Food Chem Toxicol 24:1267–72
   PubMed Web of Science ®Google Scholar
• Delbressine LPC, Balen HCJG, Seutter-Berlage F. (1982). Isolation and identification of mercapturic acid metabolites of phenyl substituted acrylate esters from urine of rats. Arch Toxicol 49:321–30
   PubMed Web of Science ®Google Scholar
• Dick RA, Kwak MK, Sutter TR, Kensler TW. (2001). Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. J Biol Chem 276:40803–10
   PubMed Web of Science ®Google Scholar
• Dugave C, Demange L. (2003). Cis-trans isomerization of organic molecules and biomolecules: implications and applications. Chem Rev 103:2475–532
   PubMed Web of Science ®Google Scholar
• Ishikawa H, Nakashima T, Inaba K, et al. (1999). Proton magnetic resonance assay of total and taurine-conjugated bile acids in bile. J Lipid Res 40:1920–4
   PubMed Web of Science ®Google Scholar
• Kaneko H. (2011). Pyrethroids: mammalian metabolism and toxicity. J Agric Food Chem 59:2786–91
   PubMed Web of Science ®Google Scholar
• Kaneko H, Matuso M, Miyamoto J. (1984). Comparative metabolism of stereoisomers of cyphenothrin and phenothrin isomers in rats. J Pestic Sci 9:237–47
   Web of Science ®Google Scholar
• Kaneko H, Ohkawa H. (1981b). Miyamoto, J, Metabolism of tetramethrin isomers in rats. J Pestic Sci 6:425–35
   Web of Science ®Google Scholar
• Kaneko H, Ohkawa H, Miyamoto J. (1981a). Comparative metabolism of fenvalerate and the [2S, αS]-isomer in rats and mice. J Pestic Sci 6:317–26
   Web of Science ®Google Scholar
• Kitamura S, Tatsumi K. (1990). Purification of NADPH-linked α,β-ketoalkene double bond reductase from rat liver. Arch Biochem Biophys 282:183–7
   PubMed Web of Science ®Google Scholar
• Matsuda J, Kuroda Y. (2002). Mitochondrial fumarase. Nippon Rinsho 60:126–9
   PubMedGoogle Scholar
• Matsuo N, Ujihara K, Shono Y, et al. (2005). Discovery and development of a novel pyrethroid insecticide ‘Metofluthrin (SumiOne®, Eminence®)’. Sumitomo Kagaku 2005-II: 1–15
   Google Scholar
• Metzler M, Neumann HG. (1977). Epoxidation of the stilbene double bond, a major pathway in aminostilbene metabolism. Xenobiotica 7:117–32
   PubMed Web of Science ®Google Scholar
• Mikata K, Isobe N, Kaneko H. (2012). Biotransformation and enzymatic reactions of synthetic pyrethroids in mammals. Top Curr Chem 314:113–36
   PubMed Web of Science ®Google Scholar
• Mori T, Ujihara K, Matsumoto O, et al. (2007). Synthetic studies of fluorine-containing compounds for household insecticides. J Fluorine Chem 128:1174–81
   Web of Science ®Google Scholar
• Sabourin PJ, Burka LT, Bechtold WE, et al. (1992). Species differences in urinary butadiene metabolites; identification of 1,2-dihydroxy-4-(N-acetylcysteinyl)butane, a novel metabolite of butadiene. Carcinogenesis 13:1633–8
   PubMed Web of Science ®Google Scholar
• Schiller J, Chung AE. (1970). Mechanism of cyclopropane ring cleavage in cyclopropanecarboxylic acid. J Biol Chem 245:6553–7
   PubMed Web of Science ®Google Scholar
• Stoffel W, Därr W. (1974). 2-Alkenal reductase isolation, properties and specificities. Hoppe-Seyler's Z physiol Chem 355:54–60
   PubMedGoogle Scholar
• Tanaka K, Inoue T, Kadota S, Kikuchi T. (1990). Metabolism of illudin S, a toxic principle of Lampteromyces japonicus, by rat liver. I. Isolation and identification of cyclopropane ring-cleavage metabolites. Xenobiotica 20:671–81
   PubMed Web of Science ®Google Scholar
• Tomigahara Y, Mori M, Shiba K, et al. (1994a). Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites. Xenobiotica 24:473–84
   PubMed Web of Science ®Google Scholar
• Tomigahara Y, Mori M, Shiba K, et al. (1994c). Metabolism of tetramethrin isomers in rat: II. Identification and quantitation of metabolites. Xenobiotica 24:1205–14
   PubMed Web of Science ®Google Scholar
• Tomigahara Y, Onogi M, Kaneko H, et al. (1999). Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482, flumioxazin) in the rat: II. Identification of reduced metabolites. J Agric Food Chem 47:2429–38
   PubMed Web of Science ®Google Scholar
• Tomigahara Y, Onogi M, Saito K, et al. (1987). Metabolism of tetramethrin isomers in rat: IV. Tissues responsible for formation of reduced and hydrated metabolites. Xenobiotica 27:961–71
   Google Scholar
• Tomigahara Y, Shiba K, Isobe N, et al. (1994b). Identification of two new types of S-linked conjugates of Etoc in rat. Xenobiotica 24:839–52
   PubMed Web of Science ®Google Scholar
• Ujihara K, Mori T, Iwasaki T, et al. (2004a). Metofluthrin: A potent new synthetic pyrethroid with high vapor activity against mosquitoes. Biosci Biotechnol Biochem 68:170–4
   PubMed Web of Science ®Google Scholar
• Ujihara K, Matsuo N, Kitahara T. (2004b). Synthesis of all stereoisomers of the norchrysanthemic acid methyl ester. Synth Commun 34:1001–10
   Web of Science ®Google Scholar
• van Doorn R, Bos RP, Brouns RME, et al. (1980). Effect of toluene and xylenes on liver glutathione and their urinary excretion as mercapturic acids in the rat. Arch Toxicol 43:293–304
   PubMed Web of Science ®Google Scholar