Norgestrel: Difference between revisions

{{Short description|Progestin medication used for birth control}}

{{Distinguish|Levonorgestrel}}

{{Use dmy dates|date=March 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 456663702

| width = 225

| alt =

| image2 = Dextronorgestrel.svg

| width2 = 225

| alt2 =

| caption = Top, '''levonorgestrel''' (CAS {{CAS|797-63-7}}); <br />Bottom: '''dextronorgestrel''' (CAS {{CAS|797-64-8}}).

<!-- | image3 = Norgestrel molecule ball.png

| width3 = 225

| alt3 = -->

<!-- Clinical data -->

| pronounce =

| tradename = Ovral, Opill, others

| DailyMedID = Norgestrel

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

| pregnancy_AU_comment =

| pregnancy_category =

| routes_of_administration = [[Oral administration|By mouth]]

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

| ATC_prefix = G03

| ATC_suffix = AA06

| ATC_supplemental = {{ATC|G03|FA10}} {{ATC|G03|FB01}} (only combinations with [[estrogen (medication)|estrogen]]s)

<!-- Legal status -->

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->

| legal_AU_comment =

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->

| legal_BR_comment =

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_CA_comment =

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->

| legal_UK_comment =

| legal_US = OTC

| legal_US_comment = <ref name="Opill FDA label">{{cite web | title=Opill- norgestrel tablet | website=DailyMed | date=4 March 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=69dfa2ac-6a7e-4587-929c-9acabd97973b | access-date=13 March 2024 | archive-date=11 March 2024 | archive-url=https://web.archive.org/web/20240311132409/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=69dfa2ac-6a7e-4587-929c-9acabd97973b | url-status=live }}</ref><ref name="FDA PR 20230713" />

| legal_EU =

| legal_EU_comment =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_UN_comment =

| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->

| bioavailability =

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<!-- Identifiers -->

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

| CAS_supplemental =

| IUPHAR_ligand =

| DrugBank = DB09389

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

| ChEMBL = 2107797

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

| ChEBI = 7630

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = dl-Norgestrel; DL-Norgestrel; (±)-Norgestrel; WY-3707; SH-70850; SH-850; FH 122-A; ''rac''-13-Ethyl-17α-ethynyl-19-nortestosterone; ''rac''-13-Ethyl-17α-ethynylestr-4-en-17β-ol-3-one

<!-- Chemical and physical data -->

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

| C=21 | H=28 | O=2

| SMILES = O=C\1CC[C@H]4C(=C/1)/CC[C@@H]3[C@@H]4CC[C@@]2(CC)[C@H]3CCC2(O)C#C

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<!-- Definition and medical uses -->

'''Norgestrel''' is a [[progestin]] which is used in [[birth control pill]]s sold under the brand name '''Ovral''' in combination with the [[estrogen]] [[ethinylestradiol]] and '''Opill''' by itself. It is also used in [[menopausal hormone therapy]].<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=PA202|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=202–|access-date=10 March 2018|archive-date=10 January 2023|archive-url=https://web.archive.org/web/20230110231919/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202|url-status=live}}</ref><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf | access-date = 10 March 2018 | archive-date = 22 August 2016 | archive-url = https://web.archive.org/web/20160822055012/http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf | url-status = live }}</ref><ref name="Drugs.com" /> It is taken [[oral administration|by mouth]].<ref name="MortonHall2012" /><ref name="pmid16112947" />

<!-- Side effects and mechanism -->

[[Side effect]]s of norgestrel include [[menstrual irregularities]], [[headache]]s, [[nausea]], and [[breast tenderness]].<ref>{{cite web | title=Learn more about Opill (0.075mg Oral Norgestrel Tablet) | website=U.S. [[Food and Drug Administration]] (FDA) | date=13 July 2023 | url=https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/opill-0075mg-oral-norgestrel-tablet-information | access-date=13 March 2024 | archive-date=9 October 2023 | archive-url=https://web.archive.org/web/20231009175334/https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/opill-0075mg-oral-norgestrel-tablet-information | url-status=live }}</ref> The most common side effects of the norgestrel include irregular bleeding, headaches, dizziness, nausea, increased appetite, abdominal pain, cramps, or bloating.<ref name="FDA PR 20230713" /> Norgestrel is a progestin, or a [[synthetic compound|synthetic]] [[progestogen (medication)|progestogen]], and hence is an [[agonist]] of the [[progesterone receptor]], the [[biological target]] of progestogens like [[progesterone]].<ref name="pmid16112947" /> It has weak [[androgen]]ic activity and no other important hormonal activity.<ref name="pmid16112947" />

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

Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966.<ref name="Ortiz-GómezSantesmases2016" /><ref name="Pohl2004" /><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=479 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA479 }}</ref> It was subsequently introduced for use in menopausal hormone therapy as well.<ref name="Drugs.com" /> Norgestrel is sometimes referred to as a "second-generation" progestin.<ref name="Carp2015">{{cite book | vauthors = Carp HJ |title=Progestogens in Obstetrics and Gynecology|url=https://books.google.com/books?id=Ik8SCAAAQBAJ&pg=PA112|date=9 April 2015|publisher=Springer|isbn=978-3-319-14385-9|page=112}}</ref> It is marketed widely throughout the world.<ref name="Drugs.com" /><ref name="IndexNominum2000" /> Norgestrel is available as a [[generic drug|generic medication]].<ref name="Drugs.com-Generic">{{cite web|url=https://www.drugs.com/availability/generic-lo-ovral-28.html|title=Generic Lo/Ovral-28 Availability|access-date=10 March 2018|archive-date=2 March 2019|archive-url=https://web.archive.org/web/20190302024543/https://www.drugs.com/availability/generic-lo-ovral-28.html|url-status=live}}</ref> In 2021, the version with [[ethinylestradiol]] was the 227th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Ethinyl Estradiol; Norgestrel - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestrel | access-date = 14 January 2024 | archive-date = 7 October 2021 | archive-url = https://web.archive.org/web/20211007114348/https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestrel | url-status = live }}</ref> In July 2023, the US [[Food and Drug Administration]] (FDA) approved norgestrel for [[over-the-counter]] sale.<ref name="FDA PR 20230713">{{Cite press release |date=13 July 2023 |title=FDA Approves First Nonprescription Daily Oral Contraceptive |url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-nonprescription-daily-oral-contraceptive |access-date=13 July 2023 |website=U.S. [[Food and Drug Administration]] (FDA) |archive-date=13 July 2023 |archive-url=https://web.archive.org/web/20230713130226/https://www.fda.gov/news-events/press-announcements/fda-approves-first-nonprescription-daily-oral-contraceptive |url-status=live }} {{PD-notice}}</ref>

{{TOC limit|3}}

==Medical uses==

Norgestrel is used in combination with [[ethinylestradiol]] or [[quinestrol]] in [[combined oral contraceptive|combined birth control pill]]s, alone in [[progestogen-only pill|progestogen-only birth control pill]]s, and in combination with [[estradiol (medication)|estradiol]] or [[conjugated estrogens]] in [[menopausal hormone therapy]].<ref name="Drugs.com" /> It has also been used as an [[emergency contraceptive]] in the [[Yuzpe regimen]].<ref name="pmid7040117">{{cite journal | vauthors = Yuzpe AA, Smith RP, Rademaker AW | title = A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent | journal = Fertility and Sterility | volume = 37 | issue = 4 | pages = 508–513 | date = April 1982 | pmid = 7040117 | doi = 10.1016/s0015-0282(16)46157-1 | doi-access = free }}</ref>

==Side effects==

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

==Pharmacology==

===Pharmacodynamics===

{{See also|Levonorgestrel#Pharmacodynamics}}

Norgestrel is a [[progestogen (medication)|progestogen]], or an [[agonist]] of the [[progesterone receptor]].<ref name="pmid16112947" /> The [[biological activity]] of norgestrel lies in the ''levo'' [[enantiomer]], [[levonorgestrel]], whereas the ''dextro'' isomer is inactive.<ref name="pmid16112947" /> As such, norgestrel is identical in its hormonal activity to levonorgestrel except that it is half as [[potency (pharmacology)|potent]] by weight.<ref name="pmid16112947" /> Levonorgestrel, and by extension norgestrel, have some [[androgen]]ic activity, but no [[estrogen (medication)|estrogen]]ic, [[antimineralocorticoid]], or [[glucocorticoid]] activity.<ref name="pmid16112947" />

{{Relative affinities of levonorgestrel and metabolites}}

The [[ovulation]]-inhibiting dose of norgestrel appears to be greater than 75{{nbsp}}μg/day, as ovulation occurred in 50 to 75% of cycles with this dosage of norgestrel in studies.<ref name="pmid22078182">{{cite journal | vauthors = Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B | title = Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide | journal = Contraception | volume = 84 | issue = 6 | pages = 549–57 | date = December 2011 | pmid = 22078182 | doi = 10.1016/j.contraception.2011.04.009 | url = }}</ref> The ovulation-inhibiting dosage of levonorgestrel, which is twice as potent as norgestrel, is approximately 50 to 60{{nbsp}}μg/day.<ref name="pmid16112947" /><ref name="pmid14670641">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | issue = Suppl 1 | pages = S7–S16 | date = December 2003 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 | url = }}</ref><ref name="pmid22078182" /> One review lists the ovulation-inhibiting dose of norgestrel as 100{{nbsp}}μg/day.<ref name="KnörrKnörr-Gärtner2013">{{cite book|vauthors=Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C|title=Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion|url=https://books.google.com/books?id=tpmgBgAAQBAJ&pg=PA583|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-642-95583-9|pages=583–|access-date=13 August 2022|archive-date=11 January 2023|archive-url=https://web.archive.org/web/20230111061914/https://books.google.com/books?id=tpmgBgAAQBAJ&pg=PA583|url-status=live}}</ref> The [[endometrial transformation dose]] of norgestrel is listed as 12{{nbsp}}mg per cycle and the [[menstrual delay test]] dose of norgestrel is listed as 0.5 to 2{{nbsp}}mg/day.<ref name="KnörrKnörr-Gärtner2013" /><ref name="LeidenbergerStrowitzki2009">{{cite book|vauthors=Leidenberger FA, Strowitzki T, Ortmann O|title=Klinische Endokrinologie für Frauenärzte|url=https://books.google.com/books?id=bqokBAAAQBAJ&pg=PA225|date=29 August 2009|publisher=Springer-Verlag|isbn=978-3-540-89760-6|pages=225,227|access-date=13 August 2022|archive-date=14 July 2023|archive-url=https://web.archive.org/web/20230714045652/https://books.google.com/books?id=bqokBAAAQBAJ&pg=PA225|url-status=live}}</ref>

===Pharmacokinetics===

{{See also|Levonorgestrel#Pharmacokinetics}}

The [[pharmacokinetics]] of norgestrel have been reviewed.<ref name="Springer2013" />

==Chemistry==

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

Norgestrel, also known as ''rac''-13-ethyl-17α-ethynyl-19-nortestosterone or as ''rac''-13-ethyl-17α-ethynylestr-4-en-17β-ol-3-one, is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is a [[racemic mixture]] of [[stereoisomer]]s dextronorgestrel (the C13α isomer; l-norgestrel, L-norgestrel, or (+)-norgestrel) and [[levonorgestrel]] (the C13β isomer; d-norgestrel, D-norgestrel, or (–)-norgestrel), the former of which is inactive (making norgestrel exactly half as [[potency (pharmacology)|potent]] as levonorgestrel).<ref name="AlldredgeCorelli2012">{{cite book|vauthors=Alldredge BK, Corelli RL, Ernst ME|title=Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs|url=https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072|date=1 February 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-713-7|pages=1072–|access-date=3 August 2017|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233115/https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072|url-status=live}}</ref><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=PA248|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5064-7|pages=248–|access-date=3 August 2017|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233116/https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248|url-status=live}}</ref> Norgestrel is more specifically a derivative of [[norethisterone]] (17α-ethynyl-19-nortestosterone) and is a member of the [[gonane]] (18-methylestrane) subgroup of the [[19-nortestosterone]] family of progestins.<ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W |title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA390|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=390–}}</ref>

===Synthesis===

[[Chemical synthesis|Chemical syntheses]] of norgestrel have been published.<ref name="Springer2013">{{cite book|title=Die Gestagene|url=https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA16|date=27 November 2013|publisher=Springer-Verlag|isbn=978-3-642-99941-3|pages=16–17,284–|access-date=19 September 2018|archive-date=14 July 2023|archive-url=https://web.archive.org/web/20230714045652/https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA16|url-status=live}}</ref>

==History==

Norgestrel was first introduced, as a birth control pill in combination with [[ethinylestradiol]], under the brand name Eugynon in Germany in 1966.<ref name="Ortiz-GómezSantesmases2016">{{cite book| vauthors = Ortiz-Gómez T, Santesmases MJ |title=Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives|url=https://books.google.com/books?id=snUGDAAAQBAJ&pg=PT175|date=22 April 2016|publisher=Taylor & Francis|isbn=978-1-317-12981-3|pages=175–|quote=The 1966 marketing campaign for Schering's second contraceptive, Eugynon, [...] (Schering AG Berline 1966, 11). [...] In 1970 [Schering] had already conducted an opinion poll among doctors in the run up to the marketing campaign for the newly introduced Neogynon. [...]}}</ref><ref name="Pohl2004">{{cite book|vauthors=Pohl WG|title=Die wissenschaftliche Welt von gestern: die Preisträger des Ignaz L. Lieben-Preises 1865-1937 und des Richard Lieben-Preises 1912-1928: ein Kapitel österreichischer Wissenschaftsgeschichte in Kurzbiografien|url=https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150|year=2004|publisher=Böhlau Verlag Wien|isbn=978-3-205-77303-0|pages=150–|quote=[The contraceptive Eugynon is launched in 1966. Neogynon follows in 1970.]|access-date=18 April 2018|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112233119/https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150|url-status=live}}</ref> It was subsequently marketed as a combined birth control pill with ethinylestradiol in the United States under the brand name Ovral in 1968, and was marketed in many other countries as well.<ref name="Publishing2013" /><ref name="Marks2010">{{cite book| vauthors = Marks L |title=Sexual Chemistry: A History of the Contraceptive Pill|url=https://books.google.com/books?id=_i-s4biQs7MC&pg=PA73|year=2010|publisher=Yale University Press|isbn=978-0-300-16791-7|pages=73–}}</ref><ref name="Drugs.com" />

The contraceptive efficacy of norgestrel was established in the US with the original approval for prescription use in 1973.<ref name="FDA PR 20230713" />

In July 2023, the FDA approved norgestrel for [[over-the-counter]] sale.<ref name="FDA PR 20230713" /><ref>{{Cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2023/017031Orig1s041SumR.pdf |title=Archived copy |access-date=13 March 2024 |archive-date=9 March 2024 |archive-url=https://web.archive.org/web/20240309031151/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2023/017031Orig1s041SumR.pdf |url-status=live }}</ref> The FDA granted the approval to Laboratoire HRA Pharma which was acquired by [[Perrigo Company plc]].<ref name="FDA PR 20230713" />

==Society and culture==

===Generic names===

Norgestrel is the [[generic term|generic name]] of the drug and its [[international nonproprietary name]], [[United States Adopted Name]], [[United States Pharmacopeia]], [[British Approved Name]], [[Dénomination Commune Française]], [[Denominazione Comune Italiana]], and [[Japanese Accepted Name]].<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="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA751|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=751–}}</ref><ref name="MortonHall2012" /><ref name="Drugs.com">{{cite web |url=https://www.drugs.com/international/norgestrel.html |title=Norgestrel - brand name list from |publisher=Drugs.com |date= |accessdate=17 September 2022 |archive-date=9 January 2021 |archive-url=https://web.archive.org/web/20210109221538/https://www.drugs.com/international/norgestrel.html |url-status=live }}</ref> It is also known as dl-norgestrel, DL-norgestrel, or (±)-norgestrel.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names===

Norgestrel is marketed under a variety of brand names including Cyclacur, Cryselle, Cyclo-Progynova, Duoluton, Elinest, Eugynon, Microgynon, Lo/Ovral, Low-Ogestrel, Logynon, Microlut, Minicon, Nordette, Neogest, Ogestrel, Ovral, Ovran, Ovranette, Ovrette, Planovar, Prempak, Progyluton, and Trinordiol among others.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA56|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2935–}}</ref>

==References==

{{Reflist}}

{{Progestogens and antiprogestogens}}

{{Androgen receptor modulators}}

{{Progesterone receptor modulators}}

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[[Category:Tertiary alcohols]]

[[Category:Ethynyl compounds]]

[[Category:Anabolic–androgenic steroids]]

[[Category:Estranes]]

[[Category:Hormonal contraception]]

[[Category:Ketones]]

[[Category:Progestogens]]