title: Enantioselective metabolism and enantiomerization of benalaxyl in mice.
abstract: The enantiomerization and enantioselective metabolism of benalaxyl in mice after a single gavage administration were investigated in the present study. The pharmacokinetic result indicated that elimination of (-)-R-benalaxyl in plasma was slightly faster with the t1/2of 26.65 h and 28.88 h for (-)-R- and (+)-S-benalaxyl, respectively. Consistent with this, elimination in tissues and excretion were also enantioselective, with (+)-S-benalaxyl enriched in all tissues, urine and feces. And formation of the metabolites also exhibited an enantioselective manner. Both benalaxyl and most of its metabolites exhibited a potent excretion to feces and urine. In addition, significant enantiomerization of benalaxyl enantiomers was observed in plasma, with a larger extent from R to S than S to R. Thus, this difference in enantiomerization may be one of the reasons to explain the enantioselective enrichment of (+)-S-benalaxyl in mice observed in this study. Data from this study proves that besides metabolic enzymes, enantiomerization could be another important factor that contributes to the enantioselective metabolism of a chiral pesticide. Thus, research at enantiomeric level is necessary for efficient risk assessment of chiral pesticides.
authors.affiliation: Tea Research Institute, Chinese Academy of Agricultural Sciences, Hangzhou 310008, China; Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing 100193, China.
authors.forename: Xinru
authors.initials: X
authors.lastname: Wang
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing 100193, China.
authors.forename: Wentao
authors.initials: W
authors.lastname: Zhu
authors.affiliation: Institute of Quality Standards & Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Qiu
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing 100193, China.
authors.forename: Dezhen
authors.initials: D
authors.lastname: Wang
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing 100193, China. Electronic address: zqzhou@cau.edu.cn.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Zhou
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D008297:Male; D051379:Mice; D010575:Pesticides / Q000737:chemistry*; D013237:Stereoisomerism; D014018:Tissue Distribution
chemical_list: D010575:Pesticides; C052866:benalaxyl; D000409:Alanine
keywords: Benalaxyl; Enantiomerization; Enantioselectivity; Metabolism; Mice