3219. Dimethisterone

Nomenclature

CAS number: 79-64-1
(6α,17β)-17-Hydroxy-6-methyl-17-(1-propynyl)androst-4-en-3-one; 6α-methyl-17-(1-propynyl)testosterone; 6α,21-dimethyl-17β-hydroxy-17α-pregn-4-en-20-yn-3-one; 6α,21-dimethylethisterone; 17α-ethynyl-6α,21-dimethyltestosterone; 17α-ethynyl-17-hydroxy-6α,21-dimethylandrost-4-en-3-one; Secrosteron (obsolete).
C23H32O2; mol wt 340.50.
C 81.13%, H 9.47%, O 9.40%.

Description and references

Orally active progestogen; formerly used in combinations as oral contraceptive. Prepn: S. P. Barton et al., J. Chem. Soc. 1959, 1957; eidem, US 2939819 (1960 to Brit. Drug Houses). Structure-activity study: G. K. Suchowsky, G. Baldratti, J. Endocrinol. 30, 159 (1964). Evaluation of risk for endometrial cancer: N. S. Weiss et al., N. Engl. J. Med. 302, 551 (1980). Review of carcinogenicity studies: IARC Monographs 21, 377-385 (1979).

Chemical structure

Properties

Crystals, mp 102°. [α]D20 +10° (c = 1 in chloroform). uv max (isopropanol): 240 nm (E1%1cm 450). Practically insol in water. Sol in ethanol; slightly sol in acetone, chloroform.

Derivative

Mixture with ethinyl estradiol.

Nomenclature

CAS number: 8015-19-8
Oracon (obsolete) (Mead Johnson).

Therapeutic Category

Progestogen.

Keywords

Progestogen