Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites.
1. Urinary and faecal metabolites in rat treated with 14C-labelled (1RS, trans)-tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl (1RS, trans)-chrysanthemate] were identified using chromatographic techniques and spectroanalyses (nmr and ms). 2. 3-Hydroxy-cyclohexane-1,2-dicarboximide was found to be a major and unique urinary metabolite, reduced at the 1,2-double bond of the 3,4,5,6-tetrahydrophthalimide moiety. 3. The major faecal metabolites were sulphonic acid conjugates, having a sulphonic acid group incorporated into the double bond of the 3,4,5,6-tetrahydrophthalimide moiety. 4. On the basis of the metabolites identified here, the major biotransformation reactions of trans-tetramethrin in rats are: (1) cleavage of the ester linkage; (2) cleavage of the imide linkage; (3) hydroxylation of the cyclohexene or cyclohexane ring of the 3,4,5,6-tetrahydrophthalimide moiety; (4) oxidation at the methyl group of the isobutenyl moiety; (5) reduction at the 1,2-double bond of the 3,4,5,6-tetrahydrophthalimide moiety; and (6) incorporation of a sulphonic acid group into the 1,2-double bond of the 3,4,5,6-tetrahydrophthalimide moiety.
Tomigahara
Y
Y
Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd, Osaka, Japan.
Mori
M
M
Shiba
K
K
Isobe
N
N
Kaneko
H
H
Nakatsuka
I
I
Yamada
H
H
D000818:Animals; D005243:Feces / Q000737:chemistry; D005260:Female; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D010084:Oxidation-Reduction; D011722:Pyrethrins / Q000378:metabolism* / Q000652:urine; D051381:Rats; D017207:Rats, Sprague-Dawley; D013451:Sulfonic Acids / Q000378:metabolism* / Q000652:urine
D011722:Pyrethrins; D013451:Sulfonic Acids; C009424:tetramethrin