A comparative molecular modeling study of dydrogesterone with other progestational agents through theoretical calculations and nuclear magnetic resonance spectroscopy

Selectivity and potency of the retroprogesterone dydrogesterone in vitro

“…This selectivity towards PR might be explained by the rigid conformation of dydrogesterone and dihydrodydrogesterone, which is suitable for its interaction with PR but not with the other steroid hormone receptors [36]. As shown previously in animal studies [14,16], and confirmed by the transactivation assays described above, dydrogesterone and 20␣-dihydrodydrogesterone had no androgenic effects and weak androgenic effects, respectively; although, both showed some anti-androgenic effects at the receptor level.…”

A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy

“…In Table 1 the most stable members of each family are reported while Table 2 shows for the 13-ethylsteroids 1-3 all the members of the family to which the global minima belong. The preferred conformation of compounds 1-5, located in the present study, corresponds, in the tetracyclic skeleton, to the geometry already determined at the same level of calculations for progesterone 6 [10]. In fact, it can be seen from Table 1 that the most stable conformation of each compound (1A, 2A, 3A, 4A, 5A, and 6A) show very close values of torsional angles and puckering coordinates.…”

“…b From ref. [10]. Table 2 Geometrical features and relative energies of the selected conformations of compounds 1-3 representative of the various orientations of the ethyl group at C13 and the hydroxyl group at C17 in the proton domain and 180.0 ppm (22,638.6 Hz) in the carbon domain.…”

“…Theoretical calculations at the B3LYP/6-31G * level, a current standard also for medium sized molecules such as steroids (see, for example, Refs. [5,9,10]), were performed for all the compounds; in addition, for the 13-ethylsteroids high field NMR experimental data were used to support the results of the calculations.…”

Expression of human aldo-keto reductase 1C2 in cell lines of peritoneal endometriosis: Potential implications in metabolism of progesterone and dydrogesterone and inhibition by progestins

“…Several progestins have been used for treatment of endometriosis, although with different success rates [10]. The retroprogesterone dydrogesterone has a better bioavailability than progesterone, and its main metabolite, 20␣-dihydrodydrogesterone, is also active [11].…”