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  • Title: The metabolism of diethylstilbestrol.
    Author: Metzler M.
    Journal: CRC Crit Rev Biochem; 1981; 10(3):171-212. PubMed ID: 6163591.
    Abstract:
    This literature review presents available data on the metabolism of diethylstilbestrol (DES) to shed light on the fate and the mechanism of toxicity of this compound. Biotransformation effects reviewed include conjugation reactions of DES such as glucuronide formation in vivo and in vitro, enterohepatic circulation of DES and its glucuronide, and formation of steroid sulfatases and sulfates; oxidative metabolism of DES (aromatic hydroxylation followed by methylation); and species differences in DES metabolism. Excretion curves for 12 animal species show vast differences; whereas urinary excretion predominates in humans, chimps, rhesus monkeys, and guinea pigs; rats, hamsters, and mice show predominately fecal elimination. The difference among species seems due to capability of biliary excretion. A molecular weight threshold seems to exist, and this may account for the varying remnants of DES housed in different species' organs. Placental transfer is another major problem. Fetuses of many species seem capable of glucurondizing DES. The formation of reactive metabolites (i.e., affinity for estradiol 17-beta receptor attachment and affinity for other proteins bound by estrogen) through oxidative biotransformation suggests that DES metabolites affect hepatic systems and may activate or transform cells to malignancy. Theories of the organotropism of DES carcinogenicity are presented, as well as a discussion of the fate of DES in the environment.
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