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A model of natural degradation of 17-α-ethinylestradiol in surface water and identification of degradation products by GC-MS

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Abstract

Over the past decade, the environment has been polluted by a wide spectrum of exogenous chemicals and environmental analysis has become one of the most progressive parts of analytical research. The aim of this work was to determine the kinetics of natural degradation, and to identify the degradation products of the massively used estrogenic drug, 17-α-ethinylestradiol. The photodegradation, oxidation and thermostability conditions were selected according to ICH requirements for pharmaceutical stability testing. A simple 72-h photodegradation study in purified water exhibited significant first-order kinetics with the kinetic constant k = 0.0303 h−1, and degradation halftime 22.8 h. The basic halftime could be reduced to 17.1 h by the addition of sea salt, and increase in temperature. Monohydroxy, dihydroxy and dehydrogenated derivatives of ethinylestradiol with intact steroidal structure were identified as major degradation products resulting from simple photodegradation. The addition of an oxidative agent significantly accelerated the degradation rate; combined with higher temperature, the degradation halftime was reduced to 1.1 h with the first-order kinetic constant k = 0.632 h−1. TOC analysis showed a notable decrease of organic mass (18% in 3 days) during oxidation experiments, and confirmed the degradation of steroidal structure.

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Acknowledgements

This study was financially supported by Charles University in Prague, project SVV 260 401.

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  1. Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Chemistry and Pharmaceutical Analysis, Charles University in Prague, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic

    Tomas Nejedly & Jiri Klimes

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  1. Tomas Nejedly
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  2. Jiri Klimes
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Correspondence to Tomas Nejedly.

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Responsible editor: Roland Kallenborn

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Nejedly, T., Klimes, J. A model of natural degradation of 17-α-ethinylestradiol in surface water and identification of degradation products by GC-MS. Environ Sci Pollut Res 24, 23196–23206 (2017). https://doi.org/10.1007/s11356-017-9743-5

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  • DOI: https://doi.org/10.1007/s11356-017-9743-5

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