Abstract
The isolation of γ-lactones from the urines of humans or animals treated with glutethimide or aminoglutethimide required an explanation. The question was studied on the glutethimide model. Potential metabolites such as β-hydroxymetabolite, γ-lactone amide, and γ-lactone acid were synthesized. Glutethimide was first administered to rats at high and normal doses. The corresponding γ-lactone amide, resulting from alcoholysis of β-hydroxyglutethimide, was also administered to rats. The amounts of the various γ-lactone derivatives isolated from the urine were discussed and it was concluded that the α-phenyl-γ-lactone was formed in vivo via β-hydroxylation of glutethimide followed by intramolecular alcoholysis. The lactone amide was then oxidized and dealkylated via an intramolecular mechanism leading to the corresponding α-phenyl-γ-lactone.
Published Version
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