Mestranol
Chemical compound / From Wikipedia, the free encyclopedia
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Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders.[1][7][8][9] It is formulated in combination with a progestin and is not available alone.[9] It is taken by mouth.[1]
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Trade names | Enovid, Norinyl, Ortho-Novum, others |
Other names | Ethinylestradiol 3-methyl ether; EEME; EE3ME; CB-8027; L-33355; RS-1044; 17α-Ethynylestradiol 3-methyl ether; 17α-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol |
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MedlinePlus | a601050 |
Routes of administration | By mouth[1] |
Drug class | Estrogen; Estrogen ether |
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Metabolites | Ethinylestradiol |
Elimination half-life | Mestranol: 50 min[2] EE: 7–36 hours[3][4][5][6] |
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ECHA InfoCard | 100.000.707 |
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Formula | C21H26O2 |
Molar mass | 310.437 g·mol−1 |
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Side effects of mestranol include nausea, breast tension, edema, and breakthrough bleeding among others.[10] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.[11] Mestranol is a prodrug of ethinylestradiol in the body.[11]
Mestranol was discovered in 1956 and was introduced for medical use in 1957.[12][13] It was the estrogen component in the first birth control pill.[12][13] In 1969, mestranol was replaced by ethinylestradiol in most birth control pills, although mestranol continues to be used in a few birth control pills even today.[14][9] Mestranol remains available only in a few countries, including the United States, United Kingdom, Japan, and Chile.[9]