6186. Mifepristone

Nomenclature

CAS number: 84371-65-3
(11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one; 11β-[4-(N,N-dimethylamino)phenyl]-17α-(prop-1-ynyl)-Δ4,9-estradiene-17β-ol-3-one; RU-486; RU-38486; Mifegyne (HMR).
C29H35NO2; mol wt 429.59.
C 81.08%, H 8.21%, N 3.26%, O 7.45%.

Description and references

Progesterone receptor antagonist with partial agonist activity. Prepn: J. G. Teutsch et al., EP 57115; eidem, US 4386085 (1982, 1983 both to Roussel-UCLAF). Pharmacology: W. Herrmann et al., C. R. Seances Acad. Sci. Ser. 3 294, 933 (1982). Pituitary and adrenal responses in primates: D. L. Healy et al., J. Clin. Endocrinol. Metab. 57, 863 (1983). Mechanism of action study: M. Rauch et al., Eur. J. Biochem. 148, 213 (1985). Clinical study as abortifacient: B. Couzinet et al., N. Engl. J. Med. 315, 1565 (1986); as postcoital contraceptive: A. Glasier et al., ibid. 327, 1041 (1992). Review of mechanism of action and clinical applications: E. E. Baulieu, Science 245, 1351-1357 (1989). Reviews: I. M. Spitz, C. W. Bardin, N. Engl. J. Med. 329, 404-412 (1993); R. N. Brogden et al., Drugs 45, 384-409 (1993).

Chemical structure

Properties

mp 150°. [α]D20 +138.5° (c = 0.5 in chloroform).

Therapeutic Category

Abortifacient.

Keywords

Abortifacient/Interceptive