13-03648. Epimestrol [Archived]

Nomenclature

CAS number: 7004-98-0
(16α,17α)-3-Methoxyestra-1,3,5(10)-triene-16,17-diol; 3-methoxy-17-epiestriol; Org-817; NSC-55975; Stimovul (Organon).
C19H26O3; mol wt 302.41.
C 75.46%, H 8.67%, O 15.87%.

Description and references

Estriol deriv, which stimulates ovulation. Prepn: J. de Visser, NL 95275 (1960 to Organon), C.A. 55, 22378d (1961); L. Caglioti, M. Magi, Tetrahedron Lett. 1962, 1261; eidem, Tetrahedron 19, 1127 (1963). 13C-NMR study: T. A. Wittstruck, K. I. H. Williams, J. Org. Chem. 38, 1542 (1973). Proton NMR and configurational study: B. Schoenecker et al., J. Prakt. Chem. 319, 419 (1977). Clinical chemistry: G. Falkay et al., Clin. Chim. Acta 44, 209 (1973). Comparative study in rats: D. Bentue-Ferrer et al., Ann. Endocrinol. 41, 203 (1980). Effects in normal men: M. Luisi et al., Reproduccion 4, 77 (1980), C.A. 93, 89260 (1980).

Chemical structure

Properties

Cryst from acetone/heptane, mp 158-160°. [α]D20 +48° (chloroform).

Therapeutic Category

Anterior pituitary activator.

Keywords

Gonad-Stimulating Principle

Status

This monograph has been retired and is no longer subject to revision or update.