User:Mr. Ibrahem/Norethisterone

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Mr. Ibrahem/Norethisterone
Clinical data
Trade namesAlone: Aygestin, Camila, Heather, Micronor, Primolut N, others
With EETooltip ethinylestradiol: Lo Loestrin, Loestrin, Microgestin, Modicon, Norinyl, Ortho-Novum, others
With E2: Activella, Activelle, Estalis, Kliogest, Necon, Novofem, Trisequens, others
Other namesNET; Norethindrone; others
AHFS/Drugs.comMonograph
MedlinePlusa604034
License data
Routes of
administration		By mouth, intramuscular injection (as NETETooltip norethisterone enanthate)
Drug classProgestogen (medication); Progestin
Legal status
Legal status
Pharmacokinetic data
Bioavailability47–73% (mean 64%)[1][2]
Protein binding97%:[3]
Albumin: 61%;[3]
SHBGTooltip Sex hormone-binding globulin: 36%[3]
MetabolismMainly CYP3A4 (liver);[4] also 5α-/5β-reductase, 3α-Tooltip 3α-hydroxysteroid dehydrogenase/3β-HSDTooltip 3β-hydroxysteroid dehydrogenase, and aromatase
Elimination half-life5.2–12.8 hours (mean 8.0 hours)[1]
Identifiers
  • (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Chemical and physical data
FormulaC20H26O2
Molar mass298.426 g·mol−1
3D model (JSmol)
Melting point203 to 204 °C (397 to 399 °F)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
  • InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1 checkY
  • Key:VIKNJXKGJWUCNN-XGXHKTLJSA-N checkY
  (verify)

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.[5] This includes for endometriosis, dysfunctional uterine bleeding, and painful periods.[5] It is used by mouth or, as norethisterone enantate, by injection into muscle.[5] It is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen.[5]

Common side effects include menstrual irregularities, headaches, nausea, and breast tenderness.[6] Other side effects may include depression, acne, increased hair growth.[6][7] It may be used as birth control when breastfeeding.[8] It is a manufactured progestin which causes the endometrium to change from the proliferative phase to the secretory phase.[6] It is sometimes referred to as a "first-generation" progestin.[9]

Norethisterone was first made in 1951 and was one of the first progestins to be developed.[10][11] It came into medical use in 1957 and was introduced in combination with an estrogen as birth control in 1963.[11][12] It is available as a generic medication.[5] In the United Kingdom 90 tablets of 5 mg costs the NHS about £4 as of 2021.[5] In the United States a month of medication costs about 9 USD.[13] In 2018, it was the 138th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[14][15]

References[edit]

  1. ^ 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.
  2. ^ 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.
  3. ^ a b c 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.
  4. ^ Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O (May 2008). "Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 56–66. doi:10.1016/j.jsbmb.2007.09.025. PMID 18356043. S2CID 10809537.
  5. ^ a b c d e f g BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. pp. 804, 806, 837. ISBN 978-0857114105.
  6. ^ a b c d "Norethindrone Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 13 November 2021.
  7. ^ "DailyMed - CAMILA- norethindrone tablet". dailymed.nlm.nih.gov. Archived from the original on 7 March 2021. Retrieved 13 November 2021.
  8. ^ "Norethindrone". Drugs and Lactation Database (LactMed). National Library of Medicine (US). 2006. Archived from the original on 5 March 2021. Retrieved 13 November 2021.
  9. ^ Robert Anthony Hatcher; Anita L. Nelson, M.D. (2007). Contraceptive Technology. Ardent Media. pp. 195–. ISBN 978-1-59708-001-9. Archived from the original on 2 January 2020. Retrieved 8 January 2018.
  10. ^ Donna Shoupe (7 November 2007). The Handbook of Contraception: A Guide for Practical Management. Springer Science & Business Media. pp. 15–. ISBN 978-1-59745-150-5. Archived from the original on 2 January 2020. Retrieved 5 October 2016.
  11. ^ a b Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 74, 76. ISBN 978-0-300-16791-7. Archived from the original on 2 January 2020. Retrieved 5 October 2016.
  12. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3. Archived from the original on 2 January 2020. Retrieved 5 October 2016.
  13. ^ "Norethindrone Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 19 October 2021. Retrieved 13 November 2021.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 12 February 2021. Retrieved 18 February 2021.
  15. ^ "Norethindrone - Drug Usage Statistics". ClinCalc. Archived from the original on 3 March 2021. Retrieved 18 February 2021.
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