Mestranol
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| AHFS/Drugs.com | International Drug Names |
| MedlinePlus | a601050 |
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Oral |
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| Synonyms | CB-8027, EE3ME, L-33355, RS-1044; 17α-Ethynyl-3-(methyloxy)estra-1,3,5(10)-trien-17β-ol |
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| ECHA InfoCard | 100.000.707 |
| Chemical and physical data | |
| Formula | C21H26O2 |
| Molar mass | 310.43 g/mol |
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Mestranol (INN, USAN, BAN, JAN) (brand names Devocin, Ovastol, Tranel), also known as ethinylestradiol 3-methyl ether (EEME), is a synthetic, steroidal estrogen that has been widely used medically. It was employed as the estrogen component in many of the first oral contraceptives, such as mestranol/noretynodrel (brand names Enovid, Enavid), and is still in use today. It was also a component of Ortho-Novum, Ortho-Novin, Femigen, and Norbiogest. In addition to its use as an oral contraceptive, mestranol has been used as a component of hormone replacement therapy.
Mestranol is the 3-methyl ether of ethinylestradiol, and is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinylestradiol, or ethinylestradiol being about 1.7 times as orally potent by weight as mestranol).
In April 1956, noretynodrel was investigated, in Puerto Rico, in the first large-scale clinical trial of a progestogen as an oral contraceptive. The trial was conducted in Puerto Rico due to the high birth rate in the country and concerns of moral censure in the United States. It was discovered early into the study that the initial chemical syntheses of noretynodrel had been contaminated with small amounts (1–2%) of the 3-methyl ether of ethinylestradiol (noretynodrel having been synthesized from ethinylestradiol). When this impurity was removed, higher rates of breakthrough bleeding occurred. As a result, mestranol, that same year (1956), was developed and serendipitously identified as a very potent synthetic estrogen (and eventually as a prodrug of ethinylestradiol), given its name, and added back to the formulation. This resulted in Enovid by G. D. Searle & Company, the first oral contraceptive and a combination of 9.85 mg noretynodrel and 150 μg mestranol per pill.
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