Norethisterone enanthate

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Norethisterone enanthate
Norethindrone enanthate.svg
Clinical data
Trade names Noristerat, Norigest, others
AHFS/Drugs.com International Drug Names
Routes of
administration
intramuscular injection
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
Synonyms SH-393
CAS Number
PubChem CID
ChemSpider
ChEMBL
ECHA InfoCard 100.021.207
Chemical and physical data
Formula C27H38O3
Molar mass 410.588 g/mol
 NYesY (what is this?)  (verify)

Norethisterone enanthate (NET-EN), also known as norethindrone enanthate, is a form of progestogen-only injectable birth control. It may be used following childbirth, miscarriage, or abortion.[1] The failure rate per year is 2 per 100 women.[2] Each dose lasts two months with up to two doses recommended.[3][1]

Side effects may include breast pain, headaches, depression, irregular menstrual periods, and pain at the site of injection.[3] Use in those with liver disease or during pregnancy is not recommended. Use appears to be okay during breastfeeding. It does not protect against sexually transmitted infections.[1] Norethisterone enanthate is an ester of norethisterone,[4] by which it works.[1] It works by stopping ovulation.[1]

Norethisterone was patented in 1951 and came into medical use in 1957.[5] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[6] The wholesale cost in the developing world is about 1.04 to 7.99 USD per 200 mg vial.[7] It has been approved in more than 40 countries including the United Kingdom and some in Europe, Central America, and Africa.[2][8] It is not available in the United States.[8]

Chemistry[edit]

It is a steroidal progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity[9]

History[edit]

It was introduced by Schering as Noristerat in 1957.[10] The drug was the first progestogen-only injectable contraceptive, preceding medroxyprogesterone acetate (Depo-Provera).[10]

See also[edit]

References[edit]

  1. ^ a b c d e "Noristerat 200mg, solution for intramuscular injection - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. Retrieved 31 December 2016. 
  2. ^ a b Committee on Contraceptive Development (U.S.) (1 January 1990). Luigi Mastroianni; Peter J. Donaldson; Thomas T. Kane, eds. Developing New Contraceptives: Obstacles and Opportunities. National Academies. pp. 38–. NAP:14119. 
  3. ^ a b WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 370. ISBN 9789241547659. Retrieved 8 December 2016. 
  4. ^ Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL (2015). "Long-acting injectable hormonal dosage forms for contraception". Pharmaceutical Research. 32 (7): 2180–91. PMID 25899076. doi:10.1007/s11095-015-1686-2. 
  5. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN 9783527607495. 
  6. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016. 
  7. ^ "Norethisterone". International Drug Price Indicator Guide. Retrieved 8 December 2016. 
  8. ^ a b Amy Whitaker; Melissa Gilliam (27 June 2014). Contraception for Adolescent and Young Adult Women. Springer. p. 96. ISBN 978-1-4614-6579-9. 
  9. ^ 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. Norethisterone and its acetate and enanthate esters are progestogens that have weak estrogenic and androgenic properties. 
  10. ^ a b Vern L. Bullough (2001). Encyclopedia of Birth Control. ABC-CLIO. pp. 145–. ISBN 978-1-57607-181-6.