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5333170 
Technical Report 
Glutathione-dependent biotransformation in rats of isomers of hexachlorocyclohexane 
Portig, J; Noack, G; Sodomann, S 
1975 
Schmiedeberg 
R99/ 1975 
PESTAB. Rat liver supernatant has been shown (Portig et al., Naunyn-Schmiedeberg's Arch. Pharmacol. 279: 185; 1973) to slowly convert the alpha1-isomer of hexachlorocyclohexane (HCH) to hydrophilic substance in a reaction that appears to be enzymic and requires the presence of glutathione. The product of the conversion has since been found to consist of at least three isomers of S-(dichlorophenyl)glutathione: 2,4-, 2,4-, and 2,5-. A mercapturic acid fraction prepared from the urine of rats given alpha-HCH yields, upon alkaline hydrolysis, the following isomers of dichlorothiophenol: 3,4- and gt; 2,4- and gt; 2,5- and gt; 2,3- and gt; 2,6-. An estimated 15-20% of the urinary metabolites produced by a rat in 4 weeks from a dose of alpha-HCH are dichlorophenylmercapturic acids, suggesting conjugation with glutathione to be a significant means for this species to dispose of alpha-HCH. The gamma- and delta-isomers of HCH appear to be subject to transformation along the same pathway, though to a lesser extent than the alpha-isomer, 3,4- and gt; 2,4- and gt; 2,5- and gt; 2,3- and gt; 2,6- and 2,4- and gt; 2,3- and gt; 2,6- and gt; 3,4- dichlorothiophenol were isolated from the urine of rats given gamma- or delta-HCH, respectively. (Author abstract by permission)