Crystallographic and spectroscopic study on a known orally active progestin

Steroids. 2015 Dec:104:137-44. doi: 10.1016/j.steroids.2015.09.007. Epub 2015 Sep 30.

Abstract

6,17α-Dimethyl-4,6-pregnadiene-3,20-dione (medrogestone, 2) is for a long time known steroid endowed with progestational activity. In order to study its crystallographic and NMR spectroscopic properties with the aim to fill the literature gap, we prepared medrogestone following a traditional procedure. A careful NMR study allowed the complete assignment of the (1)H and (13)C NMR signals not only of medrogestone but also of its synthetic intermediates. The structural and stereochemical characterizations of medrogestone together with its precursor 17α-methyl-3-ethoxy-pregna-3,5-dien-20-one were described by means of X-ray analysis, allowing a deepened conformational investigation.

Keywords: Medrogestone; NMR; Progesterone; Progestin; Steroidal hormone; X-ray.

MeSH terms

  • Administration, Oral
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Medrogestone / administration & dosage
  • Medrogestone / chemistry*
  • Models, Molecular
  • Molecular Conformation

Substances

  • Medrogestone