Norethisterone
Progestin medication / From Wikipedia, the free encyclopedia
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Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.[3][5] The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen.[5][6] It is used by mouth or, as norethisterone enanthate, by injection into muscle.[3][5][7]
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Trade names | Many |
Other names | NET; Norethindrone; NSC-9564; LG-202; Ethinylnortestosterone; Norpregneninolone; Anhydrohydroxy-norprogesterone; Ethinylestrenolone; 17α-Ethynyl-19-nortestosterone; 17α-Ethynylestra-4-en-17β-ol-3-one; 17α-Hydroxy-19-norpregn-4-en-20-yn-3-one |
AHFS/Drugs.com | Monograph |
MedlinePlus | a604034 |
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Routes of administration | By mouth, intramuscular injection (as NETETooltip norethisterone enanthate) |
Drug class | Progestogen (medication); Progestin |
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Bioavailability | 47–73% (mean 64%)[1][2] |
Protein binding | 97%:[3] Albumin: 61%;[3] SHBGTooltip Sex hormone-binding globulin: 36%[3] |
Metabolism | Mainly CYP3A4 (liver);[4] also 5α-/5β-reductase, 3α-Tooltip 3α-hydroxysteroid dehydrogenase/3β-HSDTooltip 3β-hydroxysteroid dehydrogenase, and aromatase |
Elimination half-life | 5.2–12.8 hours (mean 8.0 hours)[1] |
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ECHA InfoCard | 100.000.619 |
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Formula | C20H26O2 |
Molar mass | 298.426 g·mol−1 |
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Melting point | 203 to 204 °C (397 to 399 °F) |
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Side effects of norethisterone include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth.[8][9] Norethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[3][5] It has weak androgenic and estrogenic activity, mostly at high dosages, and no other important hormonal activity.[3][10]
Norethisterone was discovered in 1951 and was one of the first progestins to be developed.[11][12][13] It was first introduced for medical use on its own in 1957 and was introduced in combination with an estrogen for use as a birth control pill in 1963.[13][14] It is sometimes referred to as a "first-generation" progestin.[15][16] Along with desogestrel, it is one of the only progestins that is widely available as a progestogen-only "mini pill" for birth control.[17][18] Norethisterone is marketed widely throughout the world.[19] It is available as a generic medication.[20] In 2021, it was the 140th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[21][22] It is on the World Health Organization's List of Essential Medicines.[23]