title: Metabolism of tetramethrin isomers in rat. III. Stereochemistry of reduced metabolites.
abstract: 1. Three main urinary metabolites, two isomers of 3-hydroxycyclohexane-1,2-dicarboximide (3-OH-HPI-1 and 2) and 1,2-tetrahydrodicarboxylic acid (TCDA) were purified from rat treated with (1RS, trans)-tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl (1RS, trans)-chrysanthemate]. 2. To elucidate the mechanism of formation of these reduced metabolites, the stereochemistry of 3-OH-HPI-1, 3-OH-HPI-2 and TCDA was clarified by chemical reactions, spectroanalysis (nmr) and X-ray analysis. 3. The sole difference in configuration between 3-OH-HPI-1 and 3-OH-HPI-2 was found to be the orientation of the hydroxyl group to the cyclohexane ring, and both of these reduced metabolites showed cis-addition of two hydrogens. In contrast, reduction resulted in the trans form with TCDA. 4. These findings indicate the existence of two different reduction reaction mechanisms in the rat.
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd, Osaka, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Tomigahara
authors.forename: M
authors.initials: M
authors.lastname: Onogi
authors.forename: M
authors.initials: M
authors.lastname: Miki
authors.forename: K
authors.initials: K
authors.lastname: Yanagi
authors.forename: K
authors.initials: K
authors.lastname: Shiba
authors.forename: H
authors.initials: H
authors.lastname: Kaneko
authors.forename: I
authors.initials: I
authors.lastname: Nakatsuka
authors.forename: H
authors.initials: H
authors.lastname: Yamada
mesh_terms: D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006900:Hydroxylation; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011722:Pyrethrins / Q000493:pharmacokinetics*; D051381:Rats; D017207:Rats, Sprague-Dawley; D014961:X-Ray Diffraction
chemical_list: D011722:Pyrethrins; C009424:tetramethrin