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Journal of agricultural and food chemistry

Metabolism of procymidone derivatives in female rats.


PMID 19860430

Abstract

PCM-CH2OH [N-(3,5-dichlorophenyl)-1-hydroxymethyl-2-methylcyclopropane-1,2-dicarboximide] and PA-CH2OH [2-carboxyl-N-(3,5-dichlorophenyl)-1-hydroxymethyl-2-methylcyclopropane-1-carboxamide] are metabolites of the fungicide procymidone [N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide] in rat. The distribution and metabolism of PCM-CH2OH and PA-CH2OH were here clarified by analyzing plasma and tissues (liver, kidney, heart, lung, spleen and ovary) of female rats after single subcutaneous administration of [phenyl-14C]PCM-CH2OH and [phenyl-14C]PA-CH2OH at 62.5 mg/kg, respectively. In both rats dosed with PCM-CH2OH and PA-CH2OH, the radioactivity was similarly distributed into plasma and tissues, and PA-CH2OH was detected as the main metabolite in plasma, whereas PCM-CH2OH predominated in tissues except for kidney at 1 h after administration of PA-CH2OH. Furthermore, the cyclization ratio [PCM-CH2OH/(PCM-CH2OH+PA-CH2OH)] increased in tissues of PA-CH2OH dosed rats with passage of time. Both procymidone and PCM-CH2OH have convertible conformations (closed and open ring forms), so influence of pH conditions to their conversion was examined. Both compounds demonstrated closed rings under acidic conditions, and open rings under alkaline conditions. Generally, intracellar pH is kept at approximately neutral, and extracellular pH is kept at 0.6-0.7 units higher in all the animal species, so that our in vitro results supported in vivo findings.

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