Back نوريثيستيرون Arabic نوراتی سترون AZB Norethisteron Welsh Norethisteron German 19-noretisterona Spanish نوراتی سترون Persian Noretisteroni Finnish Noréthistérone French Noretisterone Italian ノルエチステロン Japanese

Norethisterone

Norethisterone
Clinical data
Trade namesMany
Other namesNET; 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.comMonograph
MedlinePlusa604034
License data
Routes of
administration		By mouth, intramuscular injection (as NETETooltip norethisterone enanthate)
Drug classProgestogen (medication); Progestin
ATC code
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.619 Edit this at Wikidata
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.[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]

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]

  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 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.
  4. ^ Cite error: The named reference pmid18356043 was invoked but never defined (see the help page).
  5. ^ 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.
  6. ^ Alden KR, Lowdermilk DL, Cashion MC, Perry SE (27 December 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.
  7. ^ Cite error: The named reference pmid2170822 was invoked but never defined (see the help page).
  8. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018405s023lbl.pdf Archived 10 February 2017 at the Wayback Machine [bare URL PDF]
  9. ^ Cite error: The named reference pmid14450719 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference HumansOrganization2007 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference DjerassiMiramontes1954 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Shoupe2007 was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference Marks2010 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  15. ^ 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.
  16. ^ Gunasheela S (14 March 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.
  17. ^ 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. PMID 24226383.
  18. ^ 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.
  19. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  20. ^ "Generic Aygestin Availability". Archived from the original on 24 August 2018. Retrieved 8 January 2018.
  21. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  22. ^ "Norethindrone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  23. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

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