Norethisterone enanthate: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 403876920

| IUPAC_name=[(9''S'',10''R'',13''S'',14''S'',17''R'')-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-17-yl] heptanoate

| image = Norethindrone enanthate.svg

| width = 250px

| image2 = Norethisterone enanthate molecule ball.png

| width2 = 250px

<!--Clinical data-->

| tradename = Noristerat, others

| Drugs.com = {{drugs.com|international|norethisterone-enanthate}}

| MedlinePlus =

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = S4

| legal_CA = <!-- Schedule III or IV (not sure) please confirm in CA-->

| legal_UK = <!-- P or POM (not sure) someone from UK please confirm-->

| legal_US = <!-- Rx-only / Schedule III, IV (not sure) please confirm in US-->

| legal_status =

| routes_of_administration = [[Intramuscular injection]]

| class = [[Progestogen (medication)|Progestogen]]; [[Progestin]]; [[Progestogen ester]]

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 3836-23-5

| ATC_suffix = AC01

| ATC_supplemental = {{ATC|G03|DC02}}

| PubChem = 229295

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB14678

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 34894

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 3187229

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 199613

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HY3S2K0J0F

| KEGG = C14486

| synonyms = NETE; NET-EN; Norethindrone enanthate; SH-393; 17α-Ethynyl-19-nortestosterone 17β-enanthate; 17α-Ethynylestra-4-en-17β-ol-3-one 17β-enanthate

<!--Chemical data-->

| C=27 | H=38 | O=3

| 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

| StdInChI = 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

| StdInChIKey = APTGJECXMIKIET-WOSSHHRXSA-N

<!-- Definition and medical uses -->

'''Norethisterone enanthate''' ('''NETE'''), also known as '''norethindrone enanthate''', is a form of [[hormonal birth control]] which is used to prevent [[pregnancy]] in women.<ref name=UK2016/><ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA886|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=886–|url-status=live|archive-url=https://web.archive.org/web/20171105201625/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA886|archive-date=5 November 2017}}</ref><ref name="IndexNominum2000B">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA750 | access-date = 30 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 750 | url-status = live | archive-url = https://web.archive.org/web/20130528233641/http://books.google.com/books?id=5GpcTQD_L2oC&pg=PA750 | archive-date = 28 May 2013}}</ref> It is used both as a form of [[progestogen-only injectable contraceptive|progestogen-only injectable birth control]] and in [[combined injectable birth control]] formulations. It may be used following [[childbirth]], [[miscarriage]], or [[abortion]].<ref name=UK2016/> The failure rate per year in preventing pregnancy for the progestogen-only formulation is 2 per 100 women.<ref name=Mas1990/> Each dose of this form lasts two months with only up to two doses typically recommended.<ref name=WHO2008/><ref name=UK2016/>

<!-- Side effects and mechanism -->

Side effects include [[breast pain]], [[headache]]s, [[depression (mood)|depression]], [[irregular menstruation|irregular menstrual periods]], and [[injection site reaction|pain at the site of injection]].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free | page=370}}</ref> Use in those with [[liver disease]] is not recommended as is use during pregnancy due to risk of [[birth defect]]s.<ref name=UK2016/> Use appears to be okay during [[breastfeeding]].<ref name=UK2016/> It does not protect against [[sexually transmitted infections]].<ref name=UK2016>{{cite web|title=Noristerat 200mg, solution for intramuscular injection - Summary of Product Characteristics (SPC) - (eMC)|url=https://www.medicines.org.uk/emc/medicine/1835|website=www.medicines.org.uk|access-date=31 December 2016|url-status=dead|archive-url=https://web.archive.org/web/20161231170329/https://www.medicines.org.uk/emc/medicine/1835|archive-date=31 December 2016}}</ref> NETE is an [[ester]] and [[prodrug]] of [[norethisterone]],<ref name=Wu2015>{{cite journal | vauthors = Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL | title = Long-acting injectable hormonal dosage forms for contraception | journal = Pharmaceutical Research | volume = 32 | issue = 7 | pages = 2180–91 | year = 2015 | pmid = 25899076 | doi = 10.1007/s11095-015-1686-2 | s2cid = 12856674}}</ref> through which it works.<ref name=UK2016/> It works as a method of birth control by stopping [[ovulation]].<ref name=UK2016/>

<!-- History, society, and culture -->

Norethisterone was [[patent]]ed in 1951 and NETE came into medical use in 1957.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=478|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA478|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220144449/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA478|archive-date=2016-12-20}}</ref><ref name="Bullough2001" /> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free}}</ref> It has been approved by itself in more than 60&nbsp;countries including the [[United Kingdom]] and some in [[Europe]], [[Central America]], and [[Africa]], and in combination with [[estradiol valerate]] in at least 36&nbsp;countries mainly in [[Latin America]].<ref name=Mas1990>{{cite book| veditors = Mastroianni L, Donaldson PJ, Kane TT |author=Committee on Contraceptive Development (U.S.)|title=Developing New Contraceptives: Obstacles and Opportunities|url=https://archive.org/details/developingnewcon00mast|url-access=registration|date=1 January 1990|publisher=National Academies|pages=[https://archive.org/details/developingnewcon00mast/page/38 38]–|isbn=9780309041478|id=NAP:14119}}</ref><ref name=Whit2014/><ref name="BagadePawar2014">{{cite journal | vauthors = Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S | title = Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control | journal = World J Pharm Pharm Sci | volume = 3 | issue = 10 | pages = 364–392 | year = 2014 | issn = 2278-4357 | url = http://www.wjpps.com/download/article/1412071798.pdf | access-date = 2018-08-02 | archive-url = https://web.archive.org/web/20170810000242/http://www.wjpps.com/download/article/1412071798.pdf | archive-date = 2017-08-10 | url-status = dead }}</ref><ref name="pmid12290848" /> It is not available in the [[United States]].<ref name=Whit2014>{{cite book| vauthors = Whitaker A, Gilliam M |title=Contraception for Adolescent and Young Adult Women|url=https://books.google.com/books?id=vMQkBAAAQBAJ&pg=PA96|date=27 June 2014|publisher=Springer|isbn=978-1-4614-6579-9|page=96|url-status=live|archive-url=https://web.archive.org/web/20171105201625/https://books.google.com/books?id=vMQkBAAAQBAJ&pg=PA96|archive-date=5 November 2017}}</ref>

==Medical uses==

NETE is used on its own as a long-lasting [[progestogen-only injectable contraceptive]] in women.<ref name=UK2016/><ref name=WHO2008/> It is administered via [[intramuscular injection]] once every two months.<ref name=UK2016 /><ref name=WHO2008 />

==Contraindications==

{{See also|Norethisterone#Contraindications|Progestin#Contraindications}}

==Side effects==

{{See also|Norethisterone#Side effects|Progestin#Side effects}}

[[Side effect]]s of NETE may include [[breast pain]], [[headache]]s, [[depression (mood)|depression]], [[irregular menstruation|irregular menstrual periods]], and [[injection site reaction|pain at the site of injection]].<ref name=WHO2008 /> It can cause [[birth defect]]s in the [[fetus]] if used during [[pregnancy]].<ref name=UK2016 />

==Overdose==

{{See also|Norethisterone#Overdose|Progestin#Overdose}}

==Interactions==

{{See also|Norethisterone#Interactions|Progestin#Interactions}}

==Pharmacology==

{{See also|Norethisterone#Pharmacology|Norethisterone#Pharmacokinetics}}

[[File:Norethisterone.svg|thumb|right|225px|[[Norethisterone]], the [[active metabolite|active form]] of NETE.]]

===Pharmacodynamics===

NETE is a [[prodrug]] of [[norethisterone]] in the body.<ref name="pmid15491776">{{cite journal | vauthors = Hapgood JP, Koubovec D, Louw A, Africander D | title = Not all progestins are the same: implications for usage | journal = Trends Pharmacol. Sci. | volume = 25 | issue = 11 | pages = 554–7 | date = November 2004 | pmid = 15491776 | doi = 10.1016/j.tips.2004.09.005}}</ref> Upon reaching circulation, it is rapidly converted into norethisterone by [[esterase]]s. Hence, as a prodrug of norethisterone, NETE has essentially the same effects as norethisterone, acting as a potent [[progestogen (medication)|progestogen]] with additional weak [[androgen]]ic and [[estrogen (medication)|estrogen]]ic activity (the latter via its [[metabolite]] [[ethinylestradiol]]).<ref name="HumansOrganization2007">{{cite book|author1=IARC Working Group on the Evaluation of Carcinogenic Risks to Humans|author2=World Health Organization|author3=International Agency for Research on Cancer|title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy|url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA417|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=417, 432|quote=Norethisterone and its acetate and enanthate esters are progestogens that have weak estrogenic and androgenic properties.|url-status=live|archive-url=https://web.archive.org/web/20171105201625/https://books.google.com/books?id=aGDU5xibtNgC&pg=PA417|archive-date=2017-11-05}}</ref> NETA has some progestogenic activity of its own, but it is unclear if NETE does similarly.<ref name="pmid15491776" />

NETE is of about 38% higher [[molecular weight]] than norethisterone due to the presence of its C17β [[enanthic acid|enanthate]] [[ester]].<ref name="Elks2014" />

{{Relative affinities of norethisterone, metabolites, and prodrugs}}

{{Parenteral potencies and durations of progestogens}}

[[File:Hormone levels in men with a single intramuscular injection of 5 mg estradiol valerate and 50 mg norethisterone enanthate in oil.png|thumb|right|450px|Hormone levels following a single intramuscular injection of [[estradiol valerate/norethisterone enanthate]] (5&nbsp;mg/50&nbsp;mg) (Mesigyna) in healthy young men.<ref name="ValleAlvarez2011" /> Testosterone levels were maximally suppressed by about 94%, to ~30&nbsp;ng/dL, when measured at day 7 post-injection.<ref name="ValleAlvarez2011" />]]

A single intramuscular injection of [[estradiol valerate/norethisterone enanthate]] (5&nbsp;mg/50&nbsp;mg) (Mesigyna) has been found to strongly suppress [[testosterone]] levels in men.<ref name="ValleAlvarez2011">{{cite thesis | type = MSc | vauthors = del Cisne Valle Alvarez D | title = Efecto de una Dosis de 50 mg de Enantato de Noretisterona y 5 mg de Valerato de Estradiol en los Niveles de Testosterona Total en Hombres Mexicanos Sanos | trans-title = Effect of a Dose of 50 mg of Norethisterone Enanthate and 5 mg of Estradiol Valerate on Total Testosterone Levels in Healthy Mexican Men | date = 11 May 2011 | publisher = National Polytechnic Institute of Mexico | url = http://repositoriodigital.ipn.mx/handle/123456789/12490}}</ref> Levels of testosterone decreased from ~503&nbsp;ng/dL at baseline to ~30&nbsp;ng/dL at the lowest point (–94%).<ref name="ValleAlvarez2011" />

===Pharmacokinetics===

[[File:Norethisterone and ethinylestradiol levels after a single intramuscular injection of 200 mg norethisterone enanthate in premenopausal women.png|thumb|right|450px|Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg NETE in premenopausal women.<ref name="pmid29522253" />]]

A single [[intramuscular injection]] of 50 to 200&nbsp;mg NETE in [[oil solution]] has been found to have a [[duration of action]] of 11 to 52&nbsp;days in terms of clinical [[biological effect]] in the [[uterus]] and on [[body temperature]] in women.<ref name="Ferin1972a">{{cite book | vauthors = Ferin J |chapter=Effects, Duration of Action and Metabolism in Man |pages=13–24 <!-- Tables on pages 17–19 --> | veditors = Tausk M |title=Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents |volume=II |url=https://books.google.com/books?id=Nv5sAAAAMAAJ |date=September 1972 |publisher=Pergamon Press |isbn=978-0080168128 |oclc=278011135}}</ref>

Similarly to oral norethisterone and [[norethisterone acetate]], intramuscular NETE has been found to form [[ethinylestradiol]] as an [[active metabolite]].<ref name="pmid29522253">{{cite journal | vauthors = Friedrich C, Berse M, Klein S, Rohde B, Höchel J | title = In Vivo Formation of Ethinylestradiol After Intramuscular Administration of Norethisterone Enantate | journal = J Clin Pharmacol | volume = 58| issue = 6| pages = 781–789| date = March 2018 | pmid = 29522253 | doi = 10.1002/jcph.1079 | s2cid = 3813229}}</ref> With a single intramuscular injection of 200&nbsp;mg NETE in premenopausal women, the mean maximum concentration of ethinylestradiol was 32% of that of a combined oral contraceptive containing 30&nbsp;μg ethinylestradiol, the maximum equivalent oral dose of ethinylestradiol observed in the first few days of exposure was 20.3&nbsp;μg/day, and the mean equivalent oral dose of ethinylestradiol over 8&nbsp;weeks was 4.41&nbsp;μg/day.<ref name="pmid29522253" /> As such, the exposure to ethinylestradiol was described as markedly lower than that of an oral contraceptive containing 30&nbsp;μg ethinylestradiol.<ref name="pmid29522253" /> The estimated conversion rate of NETE into ethinylestradiol was 0.1%, which was much lower than that observed for oral norethisterone and norethisterone enanthate (0.2–1.0%), likely due to the lack of the [[first-pass metabolism|first pass]] through the [[liver]] with [[parenteral]] administration.<ref name="pmid29522253" /> In accordance with the low levels of ethinylestradiol produced, no increase rates of [[thromboembolism]] or [[hepatic adenoma]] have been observed in [[postmarketing surveillance|post-authorization data]] of intramuscular NETE, and the medication does not resemble combined oral contraceptives containing ethinylestradiol in its [[drug safety|safety]] profile.<ref name="pmid29522253" />

==Chemistry==

{{See also|List of progestogens|Progestogen ester|List of progestogen esters|List of androgens/anabolic steroids}}

NETE, also known as norethinyltestosterone enanthate, as well as 17α-ethynyl-19-nortestosterone 17β-enanthate or 17α-ethynylestr-4-en-17β-ol-3-one 17β-enanthate, is a progestin, or [[synthetic compound|synthetic]] progestogen, of the [[19-nortestosterone]] group, and a synthetic [[estrane]] [[steroid]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is the C17β [[enanthate]] [[ester]] of norethisterone.<ref name="Elks2014" /><ref name="IndexNominum2000" /> NETE is a [[chemical derivative|derivative]] of [[testosterone]] with an [[ethynyl group]] at the C17α position, the [[methyl group]] at the C19 position removed, and an enanthate ester attached at the C17β position.<ref name="Elks2014" /><ref name="IndexNominum2000" /> In addition to testosterone, it is a combined derivative of [[nandrolone]] (19-nortestosterone) and [[ethisterone]] (17α-ethynyltestosterone).<ref name="Elks2014" /><ref name="IndexNominum2000" /> Esters related to NETE include [[norethisterone acetate]] and [[levonorgestrel butanoate]].<ref name="Elks2014" /><ref name="IndexNominum2000" />

==History==

NETE was introduced by [[Schering AG|Schering]] as Noristerat in 1957.<ref name="Bullough2001">{{cite book| vauthors = Bullough VL |title=Encyclopedia of Birth Control|url=https://books.google.com/books?id=XuX-MGTZnJoC&pg=PA145|year=2001|publisher=ABC-CLIO|isbn=978-1-57607-181-6|pages=145–|url-status=live|archive-url=https://web.archive.org/web/20171105201625/https://books.google.com/books?id=XuX-MGTZnJoC&pg=PA145|archive-date=2017-11-05}}</ref> It was the second long-acting progestogen to be used clinically, after [[hydroxyprogesterone caproate]].<ref name="pmid13583829">{{cite journal | vauthors = Boschann HW | title = Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications | journal = Ann. N. Y. Acad. Sci. | volume = 71 | issue = 5 | pages = 727–52 | date = July 1958 | pmid = 13583829 | doi = 10.1111/j.1749-6632.1958.tb46803.x | bibcode = 1958NYASA..71..727B}}</ref> The medication was the first progestogen-only injectable contraceptive, preceding [[medroxyprogesterone acetate]] (Depo-Provera).<ref name="Bullough2001"/>

==Society and culture==

===Generic names===

''Norethisterone enantate'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INNM|International Nonproprietary Name}} and {{abbrlink|BANM|British Approved Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA201|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=201–}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/norethisterone.html|title = Norethisterone}}</ref><ref name="Martindale">{{cite book | veditors = Sweetman SC |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2082 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|chapter-url=https://www.medicinescomplete.com/mc/martindale/}}</ref> It is also spelled as ''norethisterone enanthate'' and is also known as ''norethindrone enanthate'' (the {{abbrlink|USAN|United States Adopted Name}} of norethisterone being ''norethindrone'').<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Martindale" /> NETE is known by its former developmental code name ''SH-393'' as well.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Martindale" />

===Brand names===

NETE has been marketed alone as a [[progestogen-only injectable contraceptive]] under the brand names Depocon, Doryxas, NET-EN, Noristat, Noristerat, Norigest, and Nur-Isterate, and in combination with [[estradiol valerate]] as a [[combined injectable contraceptive]] under the brand names Chinese Injectable No. 3, {{not a typo|Efectimes}}, Ginediol, Mesigyna, Mesilar, Meslart, Mesocept, Mesygest, Nofertyl, Nofertyl Lafrancol, Noregyna, Norestrin, Norifam, Norigynon, Nostidyn, Sexseg, and Solouna.<ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Martindale" /><ref name="Micromedex">{{Cite web|url=https://www.micromedexsolutions.com/micromedex2/librarian/|title = Micromedex Products: Please Login}}</ref>

{{Formulations and brand names of norethisterone and esters}}

===Availability===

NETE has been approved for use alone as a [[progestogen-only injectable contraceptive]] in more than 60&nbsp;countries throughout the world including in [[Europe]], [[Latin America]], [[Asia]], and [[Africa]].<ref name="Mas1990" /><ref name="Whit2014" /><ref name="BagadePawar2014" /> Specific countries in which NETE as a standalone medication is or has been available include [[Bangladesh]], [[France]], [[Germany]], [[India]], [[Italy]], [[Malaysia]], [[Mexico]], the [[Philippines]], [[Singapore]], [[South Africa]], [[Thailand]], and the [[United Kingdom]].<ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Martindale" /><ref name="Micromedex" />

NETE has been approved for use in combination with [[estradiol valerate]] as a [[combined injectable contraceptive]] in at least 36&nbsp;countries, mostly in Latin America but also in Africa.<ref name="BagadePawar2014" /><ref name="pmid12290848">{{cite journal | vauthors = Newton JR, D'arcangues C, Hall PE | title = A review of "once-a-month" combined injectable contraceptives | journal = J Obstet Gynaecol (Lahore) | volume = 4 | issue = Suppl 1 | pages = S1–34 | year = 1994 | pmid = 12290848 | doi = 10.3109/01443619409027641}}</ref> It is or has been available in combination with estradiol valerate in [[Argentina]], the [[Bahamas]], [[Barbados]], [[Bolivia]], [[Brazil]], [[Chile]], [[Colombia]], [[Costa Rica]], the [[Dominican Republic]], [[Ecuador]], [[Egypt]], [[El Salvador]], [[Ghana]], [[Grenada]], [[Guatemala]], [[Guyana]], [[Haiti]], [[Honduras]], [[Jamaica]], [[Kenya]], [[Mexico]], [[Nicaragua]], [[Panama]], [[Paraguay]], [[Peru]], [[St. Lucia]], [[Turkey]], [[Uruguay]], [[Venezuela]], and [[Zimbabwe]].<ref name="Drugs.com" /><ref name="Martindale" /><ref name="Micromedex" /><ref name="HumansOrganization2007" />

NETE is not available in any form in the [[United States]].<ref name="Whit2014" />

==Research==

NETE was studied by [[Schering AG|Schering]] for use as a [[progestogen-only injectable contraceptive]] at a dose of 25&nbsp;mg once a month but produced poor cycle control with this regimen and was not marketed.<ref name="pmid865726">{{cite journal | vauthors = Toppozada M | title = The clinical use of monthly injectable contraceptive preparations | journal = Obstet Gynecol Surv | volume = 32 | issue = 6 | pages = 335–47 | date = June 1977 | pmid = 865726 | doi = 10.1097/00006254-197706000-00001}}</ref>

NETE has been studied for use as a potential [[male contraceptive|male hormonal contraceptive]] in combination with [[testosterone (medication)|testosterone]] in men.<ref name="pmid20933120">{{cite journal | vauthors = Nieschlag E | title = Clinical trials in male hormonal contraception | journal = Contraception | volume = 82 | issue = 5 | pages = 457–70 | year = 2010 | pmid = 20933120 | doi =10.1016/j.contraception.2010.03.020 | url = http://www.kup.at/kup/pdf/10172.pdf}}</ref>

{{clear}}

==See also==

* [[Estradiol valerate/norethisterone enantate]]

* [[Estradiol undecylate/norethisterone enanthate]]

==References==

{{Reflist}}

== External links ==

* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/norethisterone%20enanthate | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Norethisterone Enanthate}}

{{Navboxes

| title = [[Medicine|Medical uses]]

| titlestyle = background:#ccccff

| list1 =

{{Progestogens and antiprogestogens}}

{{Androgens and antiandrogens}}

{{Estrogens and antiestrogens}}

}}

{{Navboxes

| title = [[Pharmacodynamics]]

| titlestyle = background:#ccccff

| list1 =

{{Androgen receptor modulators}}

{{Estrogen receptor modulators}}

{{Progesterone receptor modulators}}

}}

{{Portal bar|Medicine}}

{{DEFAULTSORT:Norethisterone Enanthate}}

[[Category:1951 introductions]]

[[Category:Anabolic–androgenic steroids]]

[[Category:Enanthate esters]]

[[Category:Estranes]]

[[Category:Progestogen esters]]

[[Category:Progestogens]]

[[Category:Wikipedia medicine articles ready to translate]]

[[Category:Synthetic estrogens]]

[[Category:World Health Organization essential medicines]]