Norethisterone
| Clinical data | |
|---|---|
| Trade names | Norlutin, others |
| 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 |
| License data | |
| Routes of administration | By mouth |
| Drug class | Progestin |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 47–73% (mean 64%)[9][10] |
| Protein binding | 97%:[11] Albumin: 61%;[11] SHBG: 36%[11] |
| Metabolism | Mainly CYP3A4 (liver);[12] also 5α-/5β-reductase, 3α-/3β-HSD, and aromatase |
| Elimination half-life | 5.2–12.8 hours (mean 8.0 hours)[9] |
| Identifiers | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.619 |
| Chemical and physical data | |
| Formula | C20H26O2 |
| Molar mass | 298.426 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 203 to 204 °C (397 to 399 °F) |
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Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.[11][13] The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen.[13][14] It is used by mouth or, as norethisterone enanthate, by injection into muscle.[11][13][15]
Side effects of norethisterone include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth.[16][17] Norethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[11][13] It has weak androgenic and estrogenic activity, mostly at high dosages, and no other important hormonal activity.[11][18]
Norethisterone was discovered in 1951 and was one of the first progestins to be developed.[19][20][21] 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.[21][22] It is sometimes referred to as a "first-generation" progestin.[23][24] Like desogestrel and Norgestrel, Norethisterone is available as a progestogen-only "mini pill" for birth control.[25][26][27] Norethisterone is marketed widely throughout the world.[28] It is available as a generic medication.[29] In 2022, it was the 135th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[30][31] It is on the World Health Organization's List of Essential Medicines.[32]
- ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Archived from the original on 29 March 2024. Retrieved 8 June 2024.
- ^ "Camila- norethindrone tablet". DailyMed. 1 April 2024. Retrieved 29 September 2024.
- ^ "Emzahh- norethindrone tablet". DailyMed. 10 April 2023. Retrieved 29 September 2024.
- ^ "Errin- norethindrone tablet". DailyMed. 1 March 2024. Retrieved 29 September 2024.
- ^ "Heather- norethindrone tablet". DailyMed. 31 August 2021. Retrieved 29 September 2024.
- ^ "Incassia- norethindrone tablet". DailyMed. 14 September 2021. Retrieved 29 September 2024.
- ^ "Jencycla- norethindrone tablet". DailyMed. 13 December 2023. Retrieved 29 September 2024.
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MicronorLabelwas invoked but never defined (see the help page). - ^ a b Stanczyk FZ (September 2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716. S2CID 27018468.
- ^ Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
- ^ a b c d e f g Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324. Archived (PDF) from the original on 22 August 2016. Retrieved 6 September 2018.
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pmid18356043was invoked but never defined (see the help page). - ^ a b c d Taitel HF, Kafrissen ME (1995). "Norethindrone – a review of therapeutic applications". International Journal of Fertility and Menopausal Studies. 40 (4): 207–23. PMID 8520623.
- ^ Alden KR, Lowdermilk DL, Cashion MC, Perry SE (2013). Maternity and Women's Health Care – E-Book. Elsevier Health Sciences. pp. 135–. ISBN 978-0-323-29368-6. Archived from the original on 9 March 2023. Retrieved 8 January 2018.
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pmid2170822was invoked but never defined (see the help page). - ^ "Aygestin (norethindrone acetate tablets, USP)" (PDF). Archived from the original (PDF) on 10 February 2017. Retrieved 11 July 2024.
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Publishing2013was invoked but never defined (see the help page). - ^ Hatcher RA, Nelson AL (2007). Contraceptive Technology. Ardent Media. pp. 195–. ISBN 978-1-59708-001-9. Archived from the original on 10 January 2023. Retrieved 8 January 2018.
- ^ Gunasheela S (2011). Practical Management of Gynecological Problems. JP Medical Ltd. pp. 31–. ISBN 978-93-5025-240-6. Archived from the original on 9 March 2023. Retrieved 8 January 2018.
- ^ Grimes DA, Lopez LM, O'Brien PA, Raymond EG (November 2013). "Progestin-only pills for contraception". The Cochrane Database of Systematic Reviews (11): CD007541. doi:10.1002/14651858.CD007541.pub3. PMC 11975192. PMID 24226383.
- ^ Hussain SF (February 2004). "Progestogen-only pills and high blood pressure: is there an association? A literature review". Contraception. 69 (2): 89–97. doi:10.1016/j.contraception.2003.09.002. PMID 14759612.
- ^ "Opill: Package Insert / Prescribing Information". Drugs.com. Retrieved 30 September 2024.
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Drugs.comwas invoked but never defined (see the help page). - ^ "Generic Aygestin Availability". Archived from the original on 24 August 2018. Retrieved 8 January 2018.
- ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
- ^ "Norethindrone Drug Usage Statistics, United States, 2013–2022". ClinCalc. Retrieved 30 August 2024.
- ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list. Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.