1. APIs
  2. Desogestrel
  3. Metabolites
  4. 3α-Hydroxydesogestrel

3α-Hydroxydesogestrel

Structure

Notes

Primary metabolite. Rapidly oxidized to etonogestrel. Initial in vitro studies indicated that CYP2C9 and CYP2C19 were responsible for this conversion, however later human in vivo studies refuted this and indicated CYP3A4 (Korhonen et al. 2005).

References

  1. Verhoeven, C. H. J.; Gloudemans, R. H. M.; Peeters, P. A. M.; van Lier, J. J.; Verheggen, F. T. M.; Groothuis, G. M. M.; Rietjens, I.; Vos, R. M. E., Excretion and metabolism of desogestrel in healthy postmenopausal women. J. Steroid Biochem. Mol. Biol. 2001, 78 (5), 471-480.
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  2. Groh, H.; Schon, R.; Ritzau, M.; Kasch, H.; Undisz, K.; Hobe, G., Preparation of 3-ketodesogestrel metabolites by microbial transformation and chemical synthesis. Steroids 1997, 62 (5), 437-443.
    3. (View all citations for this reference)
  3. DrugBank: Desogestrel
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)
  4. Grandi, G.; Cagnacci, A.; Volpe, A. Pharmacokinetic Evaluation of Desogestrel as a Female Contraceptive. Expert Opin. Drug Metab. Toxicol. 2014, 10 (1), 1–10. (View all citations for this reference)
  5. Laine, K.; Yasar, U.; Widen, J.; Tybring, G. A Screening Study on the Liability of Eight Different Female Sex Steroids to Inhibit CYP2C9, 2C19 and 3A4 Activities in Human Liver Microsomes. Pharmacol. Toxicol. 2003, 93 (2), 77–81.
    6. (View all citations for this reference)
  6. Korhonen, T.; Tolonen, A.; Uusitalo, J.; Lundgren, S.; Jalonen, J.; Laine, K. The Role of CYP2C and CYP3A in the Disposition of 3-Keto-Desogestrel after Administration of Desogestrel. Br. J. Clin. Pharmacol. 2005, 60 (1), 69–75. (View all citations for this reference)