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Epoxidation is the preferred pathway of first-stage metabolism of abiraterone acetate in brown bullhead (Ameiurus nebulosus)

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Abstract

Twenty juvenile individuals of brown bullhead (Ameiurus nebulosus), average weight 77 g, were fed by abiraterone acetate prodrug dissolved in olive oil via gastric probe. Dose applied was 3 mg/10 g fish weight. After feeding, they were let out into aquarium and kept there for 3 days. Aquarium water containing excreted metabolites was extracted, and sample was purified and finally analyzed by means of HPLC/MS. Expected both primary (products of hydroxylation) and secondary (products of glucuronidation and sulfatation) metabolites of abiraterone acetate were identified. The NMR measurement of one of the prevailing metabolites presumed to be one of possible hydroxy-abiraterones discovered that it is not hydroxy-abiraterone but abiraterone 16,17-epoxide. Closer analysis of MS2 and MS3 spectra revealed that one of presumed hydroxy-abiraterone acetates and also some secondary metabolites are probably 16,17-epoxides.

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Funding

The academic part of this work was financially supported by the National Program of Sustainability (NPU I Lo1509). The research was conducted within the infrastructure built from the support of the Operational Programme Prague – Competitiveness (CZ.2.16/3.1.00/24023). In addition, support provided by the RECETOX Research Infrastructure (LM2015051 and CZ.02.1.01/0.0/0.0/16 013/0001761) is acknowledged.

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Correspondence to Samuel Mach.

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Responsible editor: Philippe Garrigues

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Mach, S., Jegorov, A., Kuzma, M. et al. Epoxidation is the preferred pathway of first-stage metabolism of abiraterone acetate in brown bullhead (Ameiurus nebulosus). Environ Sci Pollut Res 26, 34896–34904 (2019). https://doi.org/10.1007/s11356-019-06568-y

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  • DOI: https://doi.org/10.1007/s11356-019-06568-y

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