# Norgestrienone

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> Markdown URL: https://mediated.wiki/source/Norgestrienone.md
> Source: https://en.wikipedia.org/wiki/Norgestrienone
> Source revision: 1329007416
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 462263142
| IUPAC_name = (8''S'',13''S'',14''S'',17''R'')-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[''a'']phenanthren-3-one
| image = Norgestrienone.svg
| image_class = skin-invert-image
| width = 225px

<!--Clinical data-->
| tradename = Ogyline, Planor, Miniplanor
| pregnancy_category = 
| legal_status = 
| routes_of_administration = [By mouth](/source/Oral_administration)
| class = [Progestogen](/source/Progestogen_(medication)); [Progestin](/source/Progestin); [Androgen](/source/Androgen); [Anabolic steroid](/source/Anabolic_steroid)

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 848-21-5
| ATC_prefix = G03
| ATC_suffix = AC07
| PubChem = 13313
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12749
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 89386PYU9O 
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07220
| synonyms = RU-2010; A-301; 17α-Ethynyltrienolone; 17α-Ethynyltrenbolone; Δ<sup>9,11</sup>-Norethisterone; 17α-Ethynylestra-4,9,11-trien-17β-ol-3-one

<!--Chemical data-->
| C=20 | H=22 | O=2 
| SMILES = O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H22O2/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/h1,8,10,12,17-18,22H,4-7,9,11H2,2H3/t17-,18+,19+,20+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GVDMJXQHPUYPHP-FYQPLNBISA-N
}}
<!-- Definition and medical uses -->
'''Norgestrienone''', sold under the brand names '''Ogyline''', '''Planor''', and '''Miniplanor''', is a [progestin](/source/progestin) medication which has been used in [birth control pill](/source/birth_control_pill)s, sometimes in combination with [ethinylestradiol](/source/ethinylestradiol).<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=PA887|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=887–}}</ref><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=PA202|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=202–}}</ref><ref name="DiazPavez1978">{{cite journal | vauthors = Diaz S, Pavez M, Quinteros E, Diaz J, Robertson DN, Croxatto HB | title = Clinical trial with subdermal implants containing norgestrienone | journal = Contraception | volume = 18 | issue = 4 | pages = 429–440 | date = October 1978 | pmid = 720075 | doi = 10.1016/0010-7824(78)90027-6 }}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA751|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=751–}}</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=2122 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|chapter-url=https://www.medicinescomplete.com/|quote=Norgestrienone is a progestogen structurally related to norethisterone that has been used as an oral contraceptive. Typical doses have been 2 mg daily with an oestrogen, and 350 micrograms daily when used alone.}}</ref> It was developed by [Roussel Uclaf](/source/Roussel_Uclaf) and has been registered for use only in [France](/source/France).<ref name="IndexNominum2000" /><ref name="Martindale" /><ref name="McGuire2000">{{cite book | vauthors = McGuire JL | title = Pharmaceuticals, 4 Volume Set|url=https://books.google.com/books?id=uG9qAAAAMAAJ|year=2000|publisher=Wiley|isbn=978-3-527-29874-7|page=1580,1599}}</ref> Under the brand name '''Planor''', it has been marketed in France as 2&nbsp;mg norgestrienone and 50&nbsp;μg ethinylestradiol tablets.<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=PA455|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=455–}}</ref> It is taken [by mouth](/source/oral_administration).<ref name="Martindale" />

<!-- Side effects and mechanism -->
Norgestrienone is a progestin, or a [synthetic](/source/synthetic_compound) [progestogen](/source/progestogen_(medication)), and hence is an [agonist](/source/agonist) of the [progesterone receptor](/source/progesterone_receptor), the [biological target](/source/biological_target) of progestogens like [progesterone](/source/progesterone).<ref name="pmid1291626" /> It has some [androgen](/source/androgen)ic activity.<ref name="Axelrod1982" /><ref name="LauritzenStudd2005" /><ref name="GiulioMonosson2012" /><ref name="pmid7065053">{{cite journal | vauthors = Rozenbaum H | title = Relationships between chemical structure and biological properties of progestogens | journal = American Journal of Obstetrics and Gynecology | volume = 142 | issue = 6 Pt 2 | pages = 719–724 | date = March 1982 | pmid = 7065053 | doi = 10.1016/S0002-9378(16)32477-2 }}</ref>

<!-- History, society, and culture -->
Norgestrienone was first described in the literature in 1965.<ref name="LauritzenStudd2005" /> It is sometimes referred to as a "second-generation" progestin.<ref name="pmid9988833" /> Norgestrienone is no longer available.{{cn|date=June 2023}}

==Medical uses==
Norgestrienone was used in [hormonal contraception](/source/hormonal_contraception) to prevent [pregnancy](/source/pregnancy).<ref name="MortonHall2012" /><ref name="HumansOrganization2007" /> It has typically been used as an [oral contraceptive](/source/oral_contraceptive) at a dosage of 2&nbsp;mg/day in combination with [ethinylestradiol](/source/ethinylestradiol) and 350&nbsp;μ/day when used alone.<ref name="Martindale" />

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

==Pharmacology==
===Pharmacodynamics===
Norgestrienone has been found to possess similar [affinity](/source/affinity_(pharmacology)) for the [progesterone receptor](/source/progesterone_receptor) and [androgen receptor](/source/androgen_receptor),<ref name="pmid1291626">{{cite journal | vauthors = Loughney DA, Schwender CF | title = A comparison of progestin and androgen receptor binding using the CoMFA technique | journal = Journal of Computer-Aided Molecular Design | volume = 6 | issue = 6 | pages = 569–581 | date = December 1992 | pmid = 1291626 | doi = 10.1007/bf00126215 | s2cid = 22004130 | bibcode = 1992JCAMD...6..569L }}</ref> and in accordance, has some [androgen](/source/androgen)ic activity.<ref name="Axelrod1982">{{cite book | vauthors = Axelrod J | title = Biochemical Actions of Hormones|url=https://books.google.com/books?id=AxpPAQAAIAAJ|date=1 January 1982|publisher=Academic Press|isbn=978-0-12-452809-3}}</ref><ref name="LauritzenStudd2005">{{cite book | vauthors = Lauritzen C, Studd JW | title = Current Management of the Menopause|url=https://books.google.com/books?id=WD7S7677xUUC&pg=PA45|date=22 June 2005|publisher=CRC Press|isbn=978-0-203-48612-2|pages=45–}}</ref><ref name="GiulioMonosson2012">{{cite book | vauthors = Di Giulio RT, Monosson E | title = Interconnections Between Human and Ecosystem Health | url = https://books.google.com/books?id=dQ1JCAAAQBAJ&pg=PA60 |date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-009-1523-7|pages=60–}}</ref><ref name="pmid7065053" /> The androgenic activity of norgestrienone is greater than that of other [19-nortestosterone](/source/19-nortestosterone) derivatives due to the presence of the C9(11) [double bond](/source/double_bond), which enhances said activity.<ref name="pmid7065053" /> The ratio of [progestogen](/source/progestogen_(medication))ic to [androgen](/source/androgen)ic activity appears to be much lower for norgestrienone that it is for other 19-nortestosterone progestins such as [norethisterone](/source/norethisterone) and [levonorgestrel](/source/levonorgestrel).<ref name="pmid7382482" /><ref name="pmid7421203" /><ref name="pmid8136304" /><ref name="RaynaudOjasoo1979" /> [Gestrinone](/source/Gestrinone), the 18-methyl [analogue](/source/structural_analog) of norgestrienone, has even greater androgenic activity than norgestrienone, as this modification increases androgenic activity similarly.<ref name="pmid7065053" />

{| class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"
|+ class="nowrap" | Relative affinities (%) of norgestrienone and related steroids
|-
! Compound || {{abbrlink|PR|Progesterone receptor}} || {{abbrlink|AR|Androgen receptor}} || {{abbrlink|ER|Estrogen receptor}} || {{abbrlink|GR|Glucocorticoid receptor}} || {{abbrlink|MR|Mineralocorticoid receptor}} || {{abbrlink|SHBG|Sex hormone-binding globulin}} || {{abbrlink|CBG|Corticosteroid binding globulin}}
|-
| [Norethisterone](/source/Norethisterone) || 155–156 || 43–45 || <0.1 || 2.7–2.8 || 0.2 || ? || ?
|-
| Norgestrienone || 63–65 || 70 || <0.1 || 11 || 1.8 || ? || ?
|-
| [Levonorgestrel](/source/Levonorgestrel) || 170 || 84–87 || <0.1 || 14 || 0.6–0.9 || ? || ?
|-
| [Gestrinone](/source/Gestrinone) || 75–76 || 83–85 || <0.1, 3–10 || 77 || 3.2 || ? || ?
|- class="sortbottom"
| colspan="9" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' Values are percentages (%). Reference [ligand](/source/ligand_(biochemistry))s (100%) were [progesterone](/source/progesterone_(medication)) for the {{abbrlink|PR|progesterone receptor}}, [testosterone](/source/testosterone_(medication)) for the {{abbrlink|AR|androgen receptor}}, [{{abbr|E2|estradiol}}](/source/estradiol_(medication)) for the {{abbrlink|ER|estrogen receptor}}, {{abbrlink|DEXA|dexamethasone}} for the {{abbrlink|GR|glucocorticoid receptor}}, [aldosterone](/source/aldosterone) for the {{abbrlink|MR|mineralocorticoid receptor}}, {{abbrlink|DHT|dihydrotestosterone}} for {{abbrlink|SHBG|sex hormone-binding globulin}}, and [cortisol](/source/hydrocortisone) for {{abbrlink|CBG|Corticosteroid-binding globulin}}. '''Sources:''' <ref name="pmid7382482">{{cite journal | vauthors = Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP | title = Steroid flexibility and receptor specificity | journal = Journal of Steroid Biochemistry | volume = 13 | issue = 1 | pages = 45–59 | date = January 1980 | pmid = 7382482 | doi = 10.1016/0022-4731(80)90112-0 }}</ref><ref name="pmid7421203">{{cite journal | vauthors = Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP | display-authors = 6 | title = Steroid hormone receptors and pharmacology | journal = Journal of Steroid Biochemistry | volume = 12 | pages = 143–157 | date = January 1980 | pmid = 7421203 | doi = 10.1016/0022-4731(80)90264-2 }}</ref><ref name="pmid8136304">{{cite journal | vauthors = Ojasoo T, Raynaud JP, Doé JC | title = Affiliations among steroid receptors as revealed by multivariate analysis of steroid binding data | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 48 | issue = 1 | pages = 31–46 | date = January 1994 | pmid = 8136304 | doi = 10.1016/0960-0760(94)90248-8 | s2cid = 21336380 }}</ref><ref name="RaynaudOjasoo1979">{{cite book | vauthors = Raynaud J, Ojasoo T, Bouton M, Philibert D |title=Drug Design |year=1979 |pages=169–214 |doi=10.1016/B978-0-12-060308-4.50010-X |chapter-url= https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169|isbn=9781483216102 |chapter=Receptor Binding as a Tool in the Development of New Bioactive Steroids|series=Medicinal Chemistry: A Series of Monographs |volume=11 |publisher=Academic Press }}</ref>
|}

===Pharmacokinetics===
The [metabolism](/source/metabolism) of norgestrienone in humans has been studied.<ref name="Raynaud1971">{{cite journal | vauthors = Raynaud JP | title = Metabolism of contraceptive steroids in man. | journal = Excerpta Medica International Congress Series | date = 1970 | volume = 219 | pages = 915–922 | url = https://www.popline.org/node/480947 | archive-url = https://web.archive.org/web/20180329184746/https://www.popline.org/node/480947 | archive-date = 29 March 2018 }}</ref>

==Chemistry==
{{See also|List of progestogens|List of androgens/anabolic steroids}}

Norgestrienone, also known as 17α-ethynyl-19-nor-δ<sup>9,11</sup>-testosterone or as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, as well as δ<sup>9,11</sup>-norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), is a [synthetic](/source/synthetic_compound) [estrane](/source/estrane) [steroid](/source/steroid) and a [derivative](/source/chemical_derivative) of [testosterone](/source/testosterone_(medication)) and [19-nortestosterone](/source/19-nortestosterone).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="LaverySanfilippo2012">{{cite book | vauthors = Lavery JP, Sanfilippo JS | title = Pediatric and Adolescent Obstetrics and Gynecology|url=https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA236|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5064-7|pages=236–}}</ref> It is structurally related to the [anabolic steroid](/source/anabolic_steroid) [trenbolone](/source/trenbolone) (19-nor-δ<sup>9,11</sup>-testosterone; the non-17α-ethynylated [analogue](/source/structural_analog) of norgestrienone), the [progestogen](/source/progestogen_(medication))ic and [androgen](/source/androgen)ic steroid [gestrinone](/source/gestrinone) (the 13β-[ethyl](/source/ethyl_group) variant or 18-[methyl](/source/methyl_group) derivative of norgestrienone), and the anabolic steroid [tetrahydrogestrinone](/source/tetrahydrogestrinone) (the 18-methyl and 17α-ethyl variant of norgestrienone).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="GomelBrill2010">{{cite book | vauthors = Gomel V, Brill A |title= Reconstructive and Reproductive Surgery in Gynecology|url=https://books.google.com/books?id=C4TOBQAAQBAJ&pg=PA90|date=27 September 2010|publisher=CRC Press|isbn=978-1-84184-757-3|pages=90–}}</ref>

==History==
Norgestrienone was first described in the literature in 1965.<ref name="LauritzenStudd2005" /> It is sometimes referred to as a "second-generation" progestin based on its time of introduction.<ref name="pmid9988833">{{cite journal | vauthors = Weiss G | title = Risk of venous thromboembolism with third-generation oral contraceptives: A review | journal = American Journal of Obstetrics and Gynecology | volume = 180 | issue = 2 Pt 2 | pages = 295–301 | date = February 1999 | pmid = 9988833 | doi = 10.1016/S0002-9378(99)70721-0 }}</ref>

==Society and culture==

===Generic names===
''Norgestrienone'' is the [generic name](/source/generic_term) of the drug and its {{abbrlink|INN|International Nonproprietary Name}}.<ref name="Elks2014" /><ref name="MortonHall2012" /><ref name="IndexNominum2000" /> It is also known by its developmental code names ''RU-2010'' and ''A-301''.<ref name="Elks2014" /><ref name="MortonHall2012" /><ref name="IndexNominum2000" />

===Brand names===
Norgestrienone has been marketed under the brand names Ogyline, Planor, and Miniplanor.<ref name="Elks2014" /><ref name="MortonHall2012" /><ref name="IndexNominum2000" />

===Availability===
Norgestrienone is no longer marketed and hence is no longer available in any country.{{cn|date=June 2023}} It was previously used in [France](/source/France).<ref name="IndexNominum2000" /> The medication was never marketed in the [United States](/source/United_States).<ref name="Lednicer2009">{{cite book| vauthors = Lednicer D |title=Strategies for Organic Drug Synthesis and Design|url=https://books.google.com/books?id=fEwl6Qev-mUC&pg=PA134|date=4 March 2009|publisher=John Wiley & Sons|isbn=978-0-470-39959-0|pages=134–}}</ref>

==Research==
Norgestrienone has been studied for use in [male hormonal contraception](/source/male_hormonal_contraception).<ref name="Scheater1978">{{cite report | vauthors = Schearer SD | title = The use of progestins and androgens as a male contraceptive. Hormonal control of male fertility. | work = DHEW Publication No.(NIH). | date = 1978 | pages = 78–1097 | url =  https://www.popline.org/node/443605 | archive-url = https://web.archive.org/web/20180329184345/https://www.popline.org/node/443605 | archive-date= 29 March 2018 }}</ref>

== References ==
{{Reflist}}

{{Progestogens and antiprogestogens}}
{{Androgens and antiandrogens}}
{{Progesterone receptor modulators}}
{{Androgen receptor modulators}}

Category:Abandoned drugs
Category:Tertiary alcohols
Category:Ethynyl compounds
Category:Androgens
Category:Estranes
Category:Ketones
Category:Progestogens

---
Adapted from the Wikipedia article [Norgestrienone](https://en.wikipedia.org/wiki/Norgestrienone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Norgestrienone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.