5917. Mestranol

Nomenclature

CAS number: 72-33-3
(17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; 17α-ethynyl-3-methoxy-1,3,5(10)-estratrien-17β-ol; 17α-ethynylestradiol 3-methyl ether; Menophase (Syntex); Norquen (Syntex); Ovastol.
C21H26O2; mol wt 310.43.
C 81.25%, H 8.44%, O 10.31%.

Description and references

Orally active estrogenic steroid. Prepn: F. B. Colton, US 2666769 (1954 to Searle); J. Am. Chem. Soc. 79, 1123 (1957). Comprehensive description: H. A. El-Obeid, A. A. Al-Badr, Anal. Profiles Drug Subs. 11, 375-406 (1982). Clinical pharmacokinetics: J. W. Goldzieher et al., Contraception 21, 17 (1980). Effect on carbohydrate metabolism: W. N. Spellacy et al., Metabolism 31, 106 (1982). Randomized, double-blind clinical trials: S. Koetsawang et al., Contraception 25, 231 (1982); A. Sheth et al., ibid. 243. Evaluation of carcinogenic risk: IARC Monographs 21, 257 (1979).

Chemical structure

Properties

Crystals from methanol or acetone, mp 150-151°. uv max (methanol): 279, 287.5 nm (E1%1cm 82, 14.4). Sol in ethanol, ether, chloroform, dioxane, acetone. Slightly sol in methanol. Practically insol in water.

Note

Also used in combination with chlormadinone acetate, ethynodiol, lynestrenol, norethindrone or norethynodrel, q.q.v. Has been used in combination with megestrol acetate, q.v.

Caution

This substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-115.

Therapeutic Category

Estrogen; in combination with progestogen as oral contraceptive.

Keywords

Contraceptive (Oral); Estrogen; Steroidal