Comparative Metabolism of Stereoisomers of Cyphenothrin and Phenothrin Isomers in Rats

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  • KANEKO Hideo
    Laboratory of Biochemistry and Toxicology, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.
  • MATSUO Masatoshi
    Laboratory of Biochemistry and Toxicology, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.
  • MIYAMOTO Junshi
    Laboratory of Biochemistry and Toxicology, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.

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Other Title
  • Cyphenothrin および phenothrin 立体異性体のラットにおける比較代謝
  • Cyphenothrinおよびphenothrin立体異性体のラットにおける比較代謝〔英文〕
  • Cyphenothrin オヨビ phenothrin リッタイ イセイタイ

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Abstract

On single oral or subcutaneous administration of each of the 14C-acid, alcohol- and CN-labeled preparations of [1R, trans]- and [1R, cis]-cyphenothrin ((RS)-α-cyano-3-phenoxybenzyl-(1RS, trans/cis, 8/2) chrysanthemate) at 2 to 4mg/kg, the radiocarbon from the acid and alcohol moieties was almost completely eliminated from rats and the 14C tissue residues were generally very low. On the other hand, the radiocarbon from the CN group was somewhat slowly excreted and the hair, skin and stomach contents showed relatively higher 14C residues. The major metabolic reactions of these isomers were oxidation at the 2′- and 4′-positions of the alcohol moiety, and at the isobutenyl group and gem-dimethyl group of the acid moiety, cleavage of ester linkage and conversion of the CN group to SCN- and CO2. The [1R, trans]-isomer underwent ester cleavage to a larger extent than the [1R, cis]-isomer, which afforded the metabolites retaining ester linkage in larger amounts. There were no significant differences in the 14C tissue residues and the nature of the metabolites between the oral and subcutaneous doses, except that larger amounts of ester-cleaved metabolites were obtained with the subcutaneous than with oral doses. When the in vivo metabolic fates of [1R, trans]- and [1R, cis]-cyphenothrin were compared with the corresponding fates of [1R, trans]- and [1R, cis]-phenothrin, [1R, cis]-cyphenothrin showed higher biodegradability than [1R, cis]-phenothrin, but [1R, trans]-cyphenothrin did not differ significantly in the biodegradability from that of [1R, trans]-phenothrin. These features were in accordance with the results from the in vitro ester hydrolysis of these compounds by hepatic esterase(s). The hepatic esterase(s) hydrolyzed these compounds in the following order; [1R, trans]-phenothrin≥[1R, trans]-cyphenothrin>[1R, cis]-cyphenothrin>[1R, cis]-phenothrin. On the other hand, plasma esterase(s) did not show any trans/cis preference and hydrolyzed phenothrin to a larger extent than cyphenothrin.

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