7785. Promegestone

Nomenclature

CAS number: 34184-77-5
(17β)-17-Methyl-17-(1-oxopropyl)estra-4,9-dien-3-one; 17α-methyl-17-propionylestra-4,9-dien-3-one; 17α-methyl-17β-propionyl-19-nor-4,9-androstadien-3-one; 17α,21-dimethyl-19-norpregna-4,9-diene-3,20-dione; R-5020; RU-5020; Surgestone (Cassenne).
C22H30O2; mol wt 326.47.
C 80.94%, H 9.26%, O 9.80%.

Description and references

Synthetic progestin with no androgenic activity and with high affinity for the progesterone receptor. Prepn: J. Warnant, A. Farcilli, BE 763099; eidem, US 3679714, US 3761591 (1971, 1972, 1973 all to Roussel-UCLAF). Inhibition of gonadotropin secretion and lack of androgenic activity: F. Labrie et al., Fertil. Steril. 28, 1104 (1977). Binding studies in mouse uterus: D. Philibert, J.-P. Raynaud, Steroids 22, 89 (1973); eidem, Endocrinology 94, 627 (1974). Binding to human endometrium: eidem, Contraception 10, 457 (1974); M. Haukkamaa, T. Luukkainen, J. Steroid Biochem. 5, 447 (1974). Review and possible use in treatment of hormone-dependent breast cancer: J.-P. Raynaud, T. Ojasoo, J. Gynecol. Obstet. Biol. Reprod. 12, 697 (1983).

Chemical structure

Properties

Colorless crystals from isopropyl ether, mp 152°. Sol in acetone, benzene. Insol in water. [α]D20 -262° (c = 0.5 in ethanol). uv max in ethanol: 215, 305 nm (E1%1cm 202, 648).

Use

As radioligand for the progestin receptor.

Therapeutic Category

Progestogen.

Keywords

Progestogen