In vitro metabolism of methiocarb and carbaryl in rats, and its effect on their estrogenic and antiandrogenic activities

Environmental Toxicology and Pharmacology
Satoko TangeShigeyuki Kitamura

Abstract

In this work, we examined the metabolism of the carbamate insecticides methiocarb and carbaryl by rat liver microsomes and plasma, and its effect on their endocrine-disrupting activities. Methiocarb and carbaryl were not enzymatically hydrolyzed by rat liver microsomes, but were hydrolyzed by rat plasma, mainly to methylthio-3,5-xylenol (MX) and 1-naphthol, respectively. When methiocarb was incubated with rat liver microsomes in the presence of NADPH, methiocarb sulfoxide was formed. The hydrolysis product, MX, was also oxidized to the sulfoxide, 3,5-dimethyl-4-(methylsulfinyl)phenol (SP), by rat liver microsomes in the presence of NADPH. These oxidase activities were catalyzed by cytochrome P450 and flavin-containing monooxygenase. Methiocarb and carbaryl both exhibited estrogen receptor α (ERα) and ERβ agonistic activity. MX and 1-naphthol showed similar activities, but methiocarb sulfoxide and SP showed markedly decreased activities. On the other hand, methiocarb and carbaryl exhibited potent antiandrogenic activity in the concentration range of 1×10(-6)-3×10(-5) M. Their hydrolysis products, MX, and 1-naphthol also showed high activity, equivalent to that of flutamide. However, methiocarb sulfoxide and SP showed relatively ...Continue Reading

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Citations

May 2, 2018·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Shigeyuki Kitamura
Jan 10, 2020·Environmental and Molecular Mutagenesis·Rajnesh Kumar SharmaAman Kumar Sharma
Feb 23, 2020·Journal of Veterinary Emergency and Critical Care·Svenja Teichmann-KnorrnRené Doerfelt
Sep 27, 2016·The Journal of Toxicological Sciences·Chieri FujinoShigeyuki Kitamura
Mar 28, 2021·Environmental Research·Carmen FreireMariana F Fernández
Dec 18, 2019·Journal of Hazardous Materials·Hui LiuZhiqiang Zhou
Nov 3, 2021·Journal of Applied Toxicology : JAT·Yukio KawashimaTaisen Iguchi

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