1. APIs
  2. Norethindrone
  3. Metabolites
  4. 5α-Dihydronorethindrone

5α-Dihydronorethindrone

Structure

Notes

Major metabolite.

Progestogen Receptor Activity

Relatively high binding affinity to PR but significantly reduced progestational activity from NET.

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References

  1. Larrea, F.; Garcia-Becerra, R.; Lemus, A. E.; Garcia, G. A.; Perez-Palacios, G.; Jackson, K. J.; Coleman, K. M.; Dace, R.; Smith, C. L.; Cooney, A. J., A-ring reduced metabolites of 19-nor synthetic progestins as subtype selective agonists for ER alpha. Endocrinology 2001, 142 (9), 3791-3799.
    2. (View all citations for this reference)
  2. Pérez-Palacios, G.; Cerbón, M. A.; Pasapera, A. M.; Castro, J. I.; Enríquez, J.; Vilchis, F.; García, G. A.; Moralí, G.; Lemus, A. E. Mechanisms of Hormonal and Antihormonal Action of Contraceptive Progestins at the Molecular Level. J. Steroid Biochem. Mol. Biol. 1992, 41 (3–8), 479–485. (View all citations for this reference)

Androgen Receptor Activity

High affinity for the AR but diminished androgenic potency.

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References

  1. Pérez-Palacios, G.; Cerbón, M. A.; Pasapera, A. M.; Castro, J. I.; Enríquez, J.; Vilchis, F.; García, G. A.; Moralí, G.; Lemus, A. E. Mechanisms of Hormonal and Antihormonal Action of Contraceptive Progestins at the Molecular Level. J. Steroid Biochem. Mol. Biol. 1992, 41 (3–8), 479–485. (View all citations for this reference)

Analytical Properties & Spectra

Melting point, IR bands, 1H NMR, 13C NMR, FAB MS.

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References

  1. Lemus, A. E.; Zaga, V.; Santillan, R.; Garcia, G. A.; Grillasca, I.; Damian-Matsumura, P.; Jackson, K. J.; Cooney, A. J.; Larrea, F.; Perez-Palacios, G., The oestrogenic effects of gestodene, a potent contraceptive progestin, are mediated by its A-ring reduced metabolites. Journal of Endocrinology 2000, 165 (3), 693-702.
    2. (View all citations for this reference)

References

  1. Walker, C. J.; Cowan, D. A.; James, V. H. T.; Lau, J. C. Y.; Kicman, A. T., Doping in sport: 3. Metabolic conversion of oral norethisterone to urinary 19-norandrosterone. Steroids 2009, 74 (3), 341-349.
    2. (View all citations for this reference)
  2. Besse, J. P.; Garric, J., Progestagens for human use, exposure and hazard assessment for the aquatic environment. Environ. Pollut. 2009, 157 (12), 3485-3494.
    3. (View all citations for this reference)
  3. Schindler, A. E.; Campagnoli, C.; Druckmann, R.; Huber, J.; Pasqualini, J. R.; Schweppe, K. W.; Thijssen, J. H. H., Classification and pharmacology of progestins. Maturitas 2003, 46, 7-16.
    4. (View all citations for this reference)
  4. Stanczyk FZ. All progestins are not created equal. Steroids. 2003; 68:879-90.
    5. (View all citations for this reference)
  5. ChEMBL: Norethisterone (View all citations for this reference)
  6. Pérez-Palacios, G.; Cerbón, M. A.; Pasapera, A. M.; Castro, J. I.; Enríquez, J.; Vilchis, F.; García, G. A.; Moralí, G.; Lemus, A. E. Mechanisms of Hormonal and Antihormonal Action of Contraceptive Progestins at the Molecular Level. J. Steroid Biochem. Mol. Biol. 1992, 41 (3–8), 479–485. (View all citations for this reference)
  7. Pommier, F.; Sioufi, A.; Godbillon, J. Simultaneous Determination of Norethisterone and Six Metabolites in Human Plasma by Capillary Gas Chromatography with Mass-Selective Detection. J. Chromatogr. B Biomed. Sci. Appl. 1995, 674 (2), 155–165. (View all citations for this reference)