Norethisterone enanthate

Norethisterone enanthate
Clinical data
Trade names	Noristerat, others
Other names	NETE; NET-EN; Norethindrone enanthate; SH-393; 17α-Ethynyl-19-nortestosterone 17β-enanthate; 17α-Ethynylestra-4-en-17β-ol-3-one 17β-enanthate
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	G03DC02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only);
Identifiers
	IUPAC name [(9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate;
CAS Number	3836-23-5 ;
PubChem CID	229295;
DrugBank	DB14678 ;
ChemSpider	199613 ;
UNII	HY3S2K0J0F;
KEGG	C14486;
ChEBI	CHEBI:34894 ;
ChEMBL	ChEMBL3187229 ;
CompTox Dashboard (EPA)	DTXSID2048664 ;
ECHA InfoCard	100.021.207
Chemical and physical data
Formula	C27H38O3
Molar mass	410.598 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)C#C;
	InChI InChI=1S/C27H38O3/c1-4-6-7-8-9-25(29)30-27(5-2)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)3/h2,18,21-24H,4,6-17H2,1,3H3/t21-,22+,23+,24-,26-,27-/m0/s1; Key:APTGJECXMIKIET-WOSSHHRXSA-N;
	(verify)

Norethisterone enanthate (NETE), also known as norethindrone enanthate, is a form of hormonal birth control which is used to prevent pregnancy in women.^[1]^[2]^[3] It is used both as a form of progestogen-only injectable birth control and in combined injectable birth control formulations. It may be used following childbirth, miscarriage, or abortion.^[1] The failure rate per year in preventing pregnancy for the progestogen-only formulation is 2 per 100 women.^[4] Each dose of this form lasts two months with only up to two doses typically recommended.^[5]^[1]

Side effects include breast pain, headaches, depression, irregular menstrual periods, and pain at the site of injection.^[5] Use in those with liver disease is not recommended as is use during pregnancy due to risk of birth defects.^[1] Use appears to be okay during breastfeeding.^[1] It does not protect against sexually transmitted infections.^[1] NETE is an ester and prodrug of norethisterone,^[6] through which it works.^[1] It works as a method of birth control by stopping ovulation.^[1]

Norethisterone was patented in 1951 and NETE came into medical use in 1957.^[7]^[8] It is on the World Health Organization's List of Essential Medicines.^[9] It has been approved by itself in more than 60 countries including the United Kingdom and some in Europe, Central America, and Africa, and in combination with estradiol valerate in at least 36 countries mainly in Latin America.^[4]^[10]^[11]^[12] It is not available in the United States.^[10]

^ ^a ^b ^c ^d ^e ^f ^g ^h "Noristerat 200mg, solution for intramuscular injection - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. Archived from the original on 31 December 2016. Retrieved 31 December 2016.
^ Elks J (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 5 November 2017.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. Archived from the original on 28 May 2013. Retrieved 30 May 2012.
^ ^a ^b Committee on Contraceptive Development (U.S.) (1 January 1990). Mastroianni L, Donaldson PJ, Kane TT (eds.). Developing New Contraceptives: Obstacles and Opportunities. National Academies. pp. 38–. ISBN 9780309041478. NAP:14119.
^ ^a ^b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 370. hdl:10665/44053. ISBN 9789241547659.
^ 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. doi:10.1007/s11095-015-1686-2. PMID 25899076. S2CID 12856674.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN 9783527607495. Archived from the original on 2016-12-20.
^ Cite error: The named reference Bullough2001 was invoked but never defined (see the help page).
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ ^a ^b Whitaker A, Gilliam M (27 June 2014). Contraception for Adolescent and Young Adult Women. Springer. p. 96. ISBN 978-1-4614-6579-9. Archived from the original on 5 November 2017.
^ Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014). "Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357. Archived from the original (PDF) on 2017-08-10. Retrieved 2018-08-02.
^ Cite error: The named reference pmid12290848 was invoked but never defined (see the help page).

[UK2016-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Noristerat 200mg, solution for intramuscular injection - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. Archived from the original on 31 December 2016. Retrieved 31 December 2016.

[Elks2014-2] Elks J (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 5 November 2017.

[IndexNominum2000B-3] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. Archived from the original on 28 May 2013. Retrieved 30 May 2012.

[Mas1990-4] Committee on Contraceptive Development (U.S.) (1 January 1990). Mastroianni L, Donaldson PJ, Kane TT (eds.). Developing New Contraceptives: Obstacles and Opportunities. National Academies. pp. 38–. ISBN 9780309041478. NAP:14119.

[WHO2008-5] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 370. hdl:10665/44053. ISBN 9789241547659.

[Wu2015-6] 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. doi:10.1007/s11095-015-1686-2. PMID 25899076. S2CID 12856674.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN 9783527607495. Archived from the original on 2016-12-20.

[Bullough2001-8] Cite error: The named reference Bullough2001 was invoked but never defined (see the help page).

[WHO21st-9] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Whit2014-10] Whitaker A, Gilliam M (27 June 2014). Contraception for Adolescent and Young Adult Women. Springer. p. 96. ISBN 978-1-4614-6579-9. Archived from the original on 5 November 2017.

[BagadePawar2014-11] Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014). "Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357. Archived from the original (PDF) on 2017-08-10. Retrieved 2018-08-02.

[pmid12290848-12] Cite error: The named reference pmid12290848 was invoked but never defined (see the help page).

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