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The photochemical decomposition of the progestogenic 19-norsteroid, norethisterone, in aqueous medium

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Abstract

Norethisterone, a contraceptive 19-norsteroid, was decomposed in aqueous medium (pH 7.4) by UV-B radiation (280-320 nm). This 4-en-3-oxo-19-norsteroid was not prone to the skeletal rearrangement reactions usually observed in steroids possessing a C10-methyl group. Under the reaction conditions applied, products were formed by addition of molecules, such as solvent molecules or a second steroid molecule, and by reduction of the double bond. The prevalence of addition type reactions may have consequences for the application of norethisterone-like steroids in subdermal contraceptive devices.

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Authors and Affiliations

  1. Department of Pharmacochemistry, Center for Bio-Pharmaceutical Sciences, State University of Leiden, P.O. Box 9502, 2300, RA Leiden, The Netherlands

    A. G. J. Sedee, G. M. J. Beijersbergen Van Henegouwen & H. De Vries

  2. Laboratory of Biophysical Chemistry, Faculty of Science, University of Nijmegen, Toernooiveld, 6525, ED Nijmegen, The Netherlands

    W. Guijt & C. A. G. Haasnoot

Authors
  1. A. G. J. Sedee
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  2. G. M. J. Beijersbergen Van Henegouwen
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  3. H. De Vries
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  4. W. Guijt
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  5. C. A. G. Haasnoot
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Sedee, A.G.J., Beijersbergen Van Henegouwen, G.M.J., De Vries, H. et al. The photochemical decomposition of the progestogenic 19-norsteroid, norethisterone, in aqueous medium. Pharmaceutisch Weekblad Scientific Edition 7, 194–201 (1985). https://doi.org/10.1007/BF02307576

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  • DOI: https://doi.org/10.1007/BF02307576

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