Structural Formula Vector Image
Title: Mestranol
CAS Registry Number: 72-33-3
CAS Name: (17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol
Additional Names: 17a-ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol; 17a-ethynylestradiol 3-methyl ether
Trademarks: Menophase (Syntex); Norquen (Syntex); Ovastol
Molecular Formula: C21H26O2
Molecular Weight: 310.43
Percent Composition: C 81.25%, H 8.44%, O 10.31%
Literature 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).
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.
Melting point: mp 150-151°
Absorption maximum: uv max (methanol): 279, 287.5 nm (E1%1cm 82, 14.4)
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.
Therap-Cat: Estrogen; in combination with progestogen as oral contraceptive.
Keywords: Contraceptive (Oral); Estrogen; Steroidal.

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