Norethisterone acetate

Norethisterone acetate
Clinical data
Trade namesPrimolut-Nor, Aygestin, Gestakadin, Milligynon, Monogest, Norlutate, Primolut N, SH-420, Sovel, Styptin, others
Other namesNETA; NETAc; Norethindrone acetate; SH-420; 17α-Ethynyl-19-nortestosterone 17β-acetate; 17α-Ethynylestra-4-en-17β-ol-3-one 17β-acetate
AHFS/Drugs.comInternational Drug Names
MedlinePlusa604034
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.121 Edit this at Wikidata
Chemical and physical data
FormulaC22H28O3
Molar mass340.463 g·mol−1
3D model (JSmol)
  • C[C@@]12[C@](OC(C)=O)(C#C)CC[C@]1([C@]3([C@](CC2)([C@@]4(C(CC3)=CC(=O)CC4)[H])[H])[H])[H]
  • InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1 ☒N
  • Key:IMONTRJLAWHYGT-ZCPXKWAGSA-N ☒N
  (verify)

Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.[1][2][3][4] The medication available in low-dose and high-dose formulations and is used alone or in combination with an estrogen.[5][4][6][7] It is ingested orally.[6]

Side effects of NETA include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others.[6] NETA is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It has weak androgenic and estrogenic activity and no other important hormonal activity.[1][8] The medication is a prodrug of norethisterone in the body.[9][10]

NETA was patented in 1957 and was introduced for medical use in 1964.[11][12] It is sometimes referred to as a "first-generation" progestin.[13][14] NETA is marketed widely throughout the world.[4] It is available as a generic medication.[15]

  1. ^ 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. Archived (PDF) from the original on 2016-08-22. Retrieved 2018-09-06.
  2. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 886–. ISBN 978-1-4757-2085-3. Archived from the original on 10 January 2023. Retrieved 28 July 2017.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
  4. ^ a b c "Norethindrone Monograph for Professionals". Archived from the original on 2017-07-29. Retrieved 2018-01-23.
  5. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  6. ^ a b c "AYGESTIN® (norethindrone acetate tablets, USP)" (PDF). Archived (PDF) from the original on 10 February 2017. Retrieved 11 July 2024.
  7. ^ Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  8. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 417–. ISBN 978-92-832-1291-1. Archived from the original on 2023-01-10. Retrieved 2016-10-12. Norethisterone and its acetate and enanthate esters are progestogens that have weak estrogenic and androgenic properties.
  9. ^ Cite error: The named reference LemkeWilliams2008 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference pmid22457429 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Marks2010 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Blum2013 was invoked but never defined (see the help page).
  13. ^ 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 2023-01-10. Retrieved 2018-02-05.
  14. ^ Sulochana Gunasheela (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 5 February 2018.
  15. ^ "Generic Aygestin Availability". Archived from the original on 2018-08-24. Retrieved 2018-02-05.