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Science. 2013 Oct 18;342(6156):347-51. doi: 10.1126/science.1243192. Epub 2013 Sep 26.

Product-to-parent reversion of trenbolone: unrecognized risks for endocrine disruption.

Author information

1
Department of Civil and Environmental Engineering, University of Iowa, 4105 Seamans Center for the Engineering Arts and Sciences, Iowa City, IA 52242-1527, USA.

Abstract

Trenbolone acetate (TBA) is a high-value steroidal growth promoter often administered to beef cattle, whose metabolites are potent endocrine-disrupting compounds. We performed laboratory and field phototransformation experiments to assess the fate of TBA metabolites and their photoproducts. Unexpectedly, we observed that the rapid photohydration of TBA metabolites is reversible under conditions representative of those in surface waters (pH 7, 25°C). This product-to-parent reversion mechanism results in diurnal cycling and substantial regeneration of TBA metabolites at rates that are strongly temperature- and pH-dependent. Photoproducts can also react to produce structural analogs of TBA metabolites. These reactions also occur in structurally similar steroids, including human pharmaceuticals, which suggests that predictive fate models and regulatory risk assessment paradigms must account for transformation products of high-risk environmental contaminants such as endocrine-disrupting steroids.

PMID:
24072818
PMCID:
PMC4096139
DOI:
10.1126/science.1243192
[Indexed for MEDLINE]
Free PMC Article

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