# Quingestrone

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{{short description|Progestin medication}}
{{Distinguish|Quingestanol}}
{{Infobox drug
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = 1-[(8''S'',9''S'',10''R'',13''S'',14''S'',17''S'')-3-cyclopentyloxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1''H''-cyclopenta[''a'']phenanthren-17-yl]ethanone
| image = Quingestrone.svg
| image_class = skin-invert-image
| width = 250px

<!--Clinical data-->
| tradename = Enol-Luteovis
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = Rx-only
| routes_of_administration = [By mouth](/source/Oral_administration)
| class = [Progestogen](/source/Progestogen_(medication)); [Progestin](/source/Progestin); [Progestogen ether](/source/Progestogen_ether); [Neurosteroid](/source/Neurosteroid)

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

<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 67-95-8
| CAS_supplemental = 
| ATC_prefix = G03
| ATC_suffix = A
| PubChem = 9929903
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 8105534
| UNII = 0612VZ9I5Z
| ChEMBL = 2104568
| KEGG = D05680
| synonyms = W-3399; Progesterone 3-cyclopentyl enol ether; PCPE; 3-Cyclopentyloxypregna-3,5-dien-20-one

<!--Chemical data-->
| C=26 | H=38 | O=2
| SMILES = CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(=C4)OC5CCCC5)C)C
| StdInChI_Ref = 
| StdInChI = 1S/C26H38O2/c1-17(27)22-10-11-23-21-9-8-18-16-20(28-19-6-4-5-7-19)12-14-25(18,2)24(21)13-15-26(22,23)3/h8,16,19,21-24H,4-7,9-15H2,1-3H3/t21-,22+,23-,24-,25-,26+/m0/s1
| StdInChIKey_Ref = 
| StdInChIKey = XAVRSHOUEXATJE-FBQZJRKBSA-N
}}
<!-- Definition and medical uses -->
'''Quingestrone''', also known as '''progesterone 3-cyclopentyl enol ether''' ('''PCPE''') and sold under the brand name '''Enol-Luteovis''', is a [progestin](/source/progestin) medication which was previously used in [birth control pill](/source/birth_control_pill)s in [Italy](/source/Italy) but is now no longer marketed.<ref name="Elks2014">{{cite book | doi=10.1007/978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1058 | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer | date=14 November 2014 | veditors = Elks J, Ganellin CR | page=1058 | isbn=978-1-4757-2085-3 | oclc=898564124}}</ref><ref name="Group1965">{{cite book | url=https://books.google.com/books?id=-5hsAAAAMAAJ | title=Handbook on oral contraception | publisher=Little, Brown | author=International Planned Parenthood Federation. Medical Committee. Oral Advisory Group | year=1965 | page=18 | oclc=2717593}}</ref><ref name="pmid3559100">{{cite journal | vauthors = Larrey D, Geneve J, Pessayre D, Machayekhi JP, Degott C, Benhamou JP | title = Prolonged cholestasis after cyproheptadine-induced acute hepatitis | journal = Journal of Clinical Gastroenterology | volume = 9 | issue = 1 | pages = 102–104 | date = February 1987 | pmid = 3559100 | doi = 10.1097/00004836-198702000-00026 | quote = She had been taking an oral contraceptive combining ethinylestradiol and quingestrone since 1980. }}</ref><ref name="Hawkins1974">{{cite book| vauthors = Hawkins DF |title=Obstetric therapeutics: clinical pharmacology and therapeutics in obstetric practice|url=https://books.google.com/books?id=osNsAAAAMAAJ|year=1974|publisher=Baillière Tindall|isbn=978-0-7020-0471-1|pages=129, 138, 145}}</ref><ref name="Bentley1980">{{cite book| vauthors = Bentley PJ |title=Endocrine Pharmacology: Physiological Basis and Therapeutic Applications|url=https://books.google.com/books?id=W6M9AAAAIAAJ&pg=PA274|year=1980|publisher=CUP Archive|isbn=978-0-521-22673-8|pages=274–}}</ref> It is taken [by mouth](/source/oral_administration).<ref name="CurrentMedicineAndDrugs1962" />

<!-- Side effects and mechanism -->
Quingestrone 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="Elks2014" /><ref name="CaieKlopper1964" /><ref name="MeliWolff1965" /> It has weak [glucocorticoid](/source/glucocorticoid) activity.<ref name="Martini1966" /><ref name="SteinetzBeach1965" /><ref name="pmid4175595" />

<!-- History, society and culture -->
Quingestrone was introduced for medical use by 1962.<ref name="CurrentMedicineAndDrugs1962" /><ref name="pmid13861933" /> It is no longer available.<ref name="Micromedex" />

==Medical uses==
Quingestrone was formerly used in combination with [ethinylestradiol](/source/ethinylestradiol) or [mestranol](/source/mestranol) in [combined](/source/combined_oral_contraceptive) [birth control pill](/source/birth_control_pill)s in [Italy](/source/Italy).<ref name="Group1965" /><ref name="pmid3559100" /> The medication was studied in the clinical prevention of [miscarriage](/source/miscarriage) during [pregnancy](/source/pregnancy), but insufficient efficacy was observed at the dosage assessed (100&nbsp;mg/day orally).<ref name="BurtonWachtel1967" /><ref>{{cite book|title=Vitamins and Hormones|url=https://books.google.com/books?id=rhbTtjo7dM4C&pg=PA332|date=9 February 1973|publisher=Academic Press|isbn=978-0-08-086627-7|pages=332–}}</ref><ref name="Fraser1998">{{cite book| vauthors = Fraser IS |title=Estrogens and Progestogens in Clinical Practice|url=https://books.google.com/books?id=eO5qAAAAMAAJ|year=1998|publisher=Churchill Livingstone|isbn=978-0-443-04706-0}}</ref><ref name="GoldsteinBerrier1989">{{cite journal | vauthors = Goldstein P, Berrier J, Rosen S, Sacks HS, Chalmers TC | title = A meta-analysis of randomized control trials of progestational agents in pregnancy | journal = British Journal of Obstetrics and Gynaecology | volume = 96 | issue = 3 | pages = 265–274 | date = March 1989 | pmid = 2653414 | doi = 10.1111/j.1471-0528.1989.tb02385.x | s2cid = 72030836 }}</ref>

==Side effects==
{{See also|Progesterone (medication)#Side effects|Progestin#Side effects}}

==Pharmacology==

===Pharmacodynamics===
Along with the [retroprogesterone](/source/retroprogesterone) derivative [dydrogesterone](/source/dydrogesterone), quingestrone has been described as a "true" progesterone derivative or [progestogen](/source/progestogen_(medication)) due to its close similarity to natural progesterone.<ref name="Wachtel1969">{{cite book | url=https://books.google.com/books?id=AcRsAAAAMAAJ | title=Exfoliative cytology in gynaecological practice | publisher=Appleton-Century-Crofts | vauthors = Wachtel EG | year=1969 | page=134 | isbn=9780407169012 | lccn=77008744}}</ref><ref name="pmid13861933">{{cite journal | vauthors = Appleby B | title = Norethisterone in the control of menopausal symptoms | journal = Lancet | volume = 1 | issue = 7226 | pages = 407–409 | date = February 1962 | pmid = 13861933 | doi = 10.1016/s0140-6736(62)91363-6 | quote = Dr. Appleby would be doing a scientific service if he extended his trial using [...] preferably, a true progesterone derivative, such as [...] progesterone cyclopentyl enol ether ('Enol Luteovis', Vister). }}</ref> Similarly to progesterone, dydrogesterone, and [hydroxyprogesterone caproate](/source/hydroxyprogesterone_caproate), quingestrone is a pure progestogen and lacks any [androgen](/source/androgen)ic effects.<ref name="BairdKerr1969">{{cite book | vauthors = Baird D, Kerr JM  | url=https://books.google.com/books?id=jbwwAAAAIAAJ | title=Combined textbook of obstetrics and gynæcology for students and practitioners | publisher=E. & S. Livingstone | year=1969 |isbn = 9780443000454| lccn=70360656}}</ref> As such, it poses no risk of androgenic [side effect](/source/side_effect)s or [virilizing](/source/virilization) [teratogen](/source/teratogen)ic effects on female fetuses.<ref name="BairdKerr1969" /> Quingestrone is said to influence the [hypothalamic–pituitary–adrenal axis](/source/hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis) similarly to [progesterone](/source/progesterone_(medication)) and [medroxyprogesterone acetate](/source/medroxyprogesterone_acetate), producing [adrenal suppression](/source/adrenal_suppression) at sufficiently high doses, and this suggests that it possesses weak [glucocorticoid](/source/glucocorticoid) activity similarly to progesterone.<ref name="Martini1966">{{cite book | url=https://books.google.com/books?id=mp3wAAAAMAAJ | title=Neuroendocrinology | publisher=Academic Press | vauthors = Martini L | year=1966 | page=331 | isbn=9780124753525 | lccn=66026256}}</ref><ref name="SteinetzBeach1965">{{cite journal| vauthors = Steinetz BG, Beach VL, DiPasquale G, Battista Jr JV |title=Effects of different gestagenic steroid types on plasma-free corticosteroid levels in ACTH-treated rats|journal=Steroids|volume=5|issue=1|year=1965|pages=93–108|issn=0039-128X|doi=10.1016/0039-128X(65)90134-0}}</ref><ref name="pmid4175595">{{cite journal | vauthors = Gaunt R, Steinetz BG, Chart JJ | title = Pharmacologic alteration of steroid hormone functions | journal = Clinical Pharmacology and Therapeutics | volume = 9 | issue = 5 | pages = 657–681 | date = 1968 | pmid = 4175595 | doi = 10.1002/cpt196895657 | quote = An interesting substance which has received little attention is the 3-cyclopentyl enol ether of progesterone (quingestrone). It is a very weak progestational agent, requiring 50 mg. per rat for pregnancy maintenance. 100 At this dose quingestrone reduced adrenal weight in male rats to the level observed after hypophysectomy and prevented any rise in plasma corticosteroids in response to a maximally stimulating dose of ACTH.H5 This strongly suggests a direct adrenal effect although the substance may in addition suppress ACTH secretion. It is doubtful, however, that progestational agents have clinically important effects on the human adrenal in the doses conventionally used. Nevertheless, in view of the prolonged exposure of women to gestogens for contraception, this factor deserves continued surveillance. | s2cid = 38695246 }}</ref>

Quingestrone is a very weak progestogen.<ref name="MeliWolff1965" /><ref name="pmid4175595" /> When administered [orally](/source/oral_administration) or [intraperitoneally](/source/intraperitoneal_administration) in animals, the medication showed 1/80 and 1/20 the potency of [subcutaneously injected](/source/subcutaneous_injection) progesterone, respectively.<ref name="MeliWolff1965" /> Similarly, oral doses of quingestrone of 10 to 20&nbsp;times those of subcutaneous progesterone were insufficient to maintain [pregnancy](/source/pregnancy) in animals, and oral or intraperitoneal doses of quingestrone 20 to 40&nbsp;times those of oral or intraperitoneal progesterone were unable to potentiate [hexobarbital](/source/hexobarbital)-induced [anesthesia](/source/anesthesia) in animals (which progesterone does and is thought to do by inhibiting the [hepatic](/source/liver) [metabolism](/source/metabolism) of [barbiturate](/source/barbiturate)s).<ref name="MeliWolff1965" /> With oral administration of equal doses of progesterone and quingestrone in animals, 3 to 4&nbsp;times less [pregnanediol](/source/pregnanediol) was recovered from [urine](/source/urine) with quingestrone.<ref name="MeliWolff1965" /> The fact that quingestrone is more potent by intraperitoneal than oral administration in animals suggests that it is transformed into a less active [metabolite](/source/metabolite) in the [intestine](/source/intestine)s.<ref name="MeliWolff1965" />

The effective dosage of quingestrone in the [menstrual delay test](/source/menstrual_delay_test) has been studied.<ref name="pmid952300">{{cite journal | vauthors = Edgren RA, Sturtevant FM | title = Potencies of oral contraceptives | journal = American Journal of Obstetrics and Gynecology | volume = 125 | issue = 8 | pages = 1029–1038 | date = August 1976 | pmid = 952300 | doi = 10.1016/0002-9378(76)90804-8 }}</ref>

Quingestrone has no [anesthetic](/source/anesthetic) effect in animals, in contrast to progesterone.<ref name="Junkmann1968">{{cite book| vauthors = Junkmann K |title=Die Gestagene|url=https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA524|date=1968|publisher=Springer-Verlag|isbn=978-3-642-99941-3|pages=10,275,524}}</ref><ref name="ErcoliGardi1960">{{cite journal| vauthors = Ercoli A, Gardi R |title=Δ<sup>4-3</sup>-Keto Steroidal Enol Ethers. Paradoxical Dependency of Their Effectiveness on the Administration Route|journal=Journal of the American Chemical Society|volume=82|issue=3|year=1960|pages=746–748|issn=0002-7863|doi=10.1021/ja01488a062}}</ref>

===Pharmacokinetics===
Quingestrone has been suggested to act as a [prodrug](/source/prodrug) of progesterone via slow [hydrolysis](/source/hydrolysis) in the body.<ref name="BurtonWachtel1967">{{cite journal | vauthors = Burton ER, Wachtel EG | title = A clinical trial and cytological assessment of enol LUTEOVIS IN THE TREATMENT OF THREATENED AND RECURRENT ABORTION | journal = The Journal of Obstetrics and Gynaecology of the British Commonwealth | volume = 74 | issue = 4 | pages = 533–536 | date = August 1967 | pmid = 5340429 | doi = 10.1111/j.1471-0528.1967.tb03986.x | s2cid = 31602503 }}</ref><ref name="CharmanPorter1996">{{cite journal| vauthors = Charman WN, Porter CJ |title=Lipophilic prodrugs designed for intestinal lymphatic transport|journal=Advanced Drug Delivery Reviews|volume=19|issue=2|year=1996|pages=149–169|issn=0169-409X|doi=10.1016/0169-409X(95)00105-G}}</ref> Indeed, it produces similar [metabolite](/source/metabolite)s (e.g., [pregnanediol](/source/pregnanediol)s and [allopregnanediol](/source/allopregnanediol)s) as progesterone,<ref name="BurtonWachtel1967" /><ref name="pmid18472981">{{cite journal | vauthors = Fatouros DG, Karpf DM, Nielsen FS, Mullertz A | title = Clinical studies with oral lipid based formulations of poorly soluble compounds | journal = Therapeutics and Clinical Risk Management | volume = 3 | issue = 4 | pages = 591–604 | date = August 2007 | pmid = 18472981 | pmc = 2374933 }}</ref> although with differing ratios,<ref name="popline.org">{{Cite web | url=http://www.popline.org/node/474452 |title = POPLINE retirement|date = 2019-09-06}}</ref><ref name="Hawkins1974" /> and notably is the only progestin that is known to produce pregnanediol as a metabolite.<ref name="CurrentMedicineAndDrugs1962">{{cite book | url=https://books.google.com/books?id=auc1AQAAIAAJ | title=Current Medicine and Drugs | year=1962 | quote=Enol Luteovis (3 cyclo-pentyl enol ether of progesterone) is the only oral progestin producing pregnanediol as a metabolite. It is not very potent and probably carries very little risk of producing virilizing effects on a female foetus. Thus it is more closely related to progesterone than the other synthetic progestins. | issn=0590-4048}}</ref> Subsequent research has cast doubt on the notion that quingestrone is a prodrug of progesterone however, and indicates that it instead is directly [metabolized](/source/metabolism) into pregnanediols without [intermediate](/source/metabolic_intermediate) conversion into progesterone.<ref name="MeliWolff1965">{{cite journal | vauthors = Meli A, Wolff A, Lucker WE, Steinetz BG | title = The Biological Profile of Progesterone 3-Cyclopentyl Enol Ether as Compared with That of Progesterone | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 118 | issue = 3 | pages = 714–717 | date = March 1965 | pmid = 14264537 | doi = 10.3181/00379727-118-29947 | s2cid = 11891451 }}</ref> Based on its [chemical structure](/source/chemical_structure), quingestrone may be transformed into [3α-dihydroprogesterone](/source/3%CE%B1-dihydroprogesterone) and/or [3β-dihydroprogesterone](/source/3%CE%B2-dihydroprogesterone) and then further metabolized into [pregnanolone](/source/pregnanolone)s and pregnanediols. 3β-Dihydroprogesterone has been reported to possess about the same [progestogen](/source/progestogen_(medication))ic [potency](/source/potency_(pharmacology)) as [progesterone](/source/progesterone_(medication)) in the [Clauberg test](/source/Clauberg_test), whereas 3α-dihydroprogesterone was not assessed.<ref name="pmid919010">{{cite journal | vauthors = Junkermann H, Runnebaum B, Lisboa BP | title = New progesterone metabolites in human myometrium | journal = Steroids | volume = 30 | issue = 1 | pages = 1–14 | date = July 1977 | pmid = 919010 | doi = 10.1016/0039-128X(77)90131-3 | quote = In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available. | s2cid = 28420255 }}</ref><ref name="pmid13480263">{{cite journal | vauthors = Pincus G, Miyake T, Merrill AP, Longo P | title = The bioassay of progesterone | journal = Endocrinology | volume = 61 | issue = 5 | pages = 528–533 | date = November 1957 | pmid = 13480263 | doi = 10.1210/endo-61-5-528 | doi-access = free }}</ref>

Relative to progesterone, quingestrone shows improved [pharmacokinetics](/source/pharmacokinetics), including higher [potency](/source/potency_(pharmacology)),<ref name="popline.org"/> [oral activity](/source/oral_administration),<ref name="Lee1965">{{cite journal | url=https://books.google.com/books?id=IhU-AQAAIAAJ | title=The ... Year Book of Obstetrics and Gynecology | publisher=Year Book Publishers | vauthors = De Lee JB | journal=Yearbook of Obstetrics and Gynecology (O) | year=1965 | page=150 | issn=0084-3911 | lccn=cdr38000020}}</ref> and a longer [terminal half-life](/source/terminal_half-life) and hence [duration of action](/source/duration_of_action).<ref name="CharmanPorter1996" /> This is considered to be due to its higher [lipophilicity](/source/lipophilicity),<ref name="CharmanPorter1996" /> being stored into and slowly released from [fat](/source/fat).<ref name="Bentley1980" /><ref name="BurtonWachtel1967" /> Quingestrone also shows slower [metabolism](/source/metabolism) and more stable blood levels, with a longer time to peak concentrations and a less intense peak compared to progesterone.<ref name="CaieKlopper1964">{{cite journal | vauthors = Caie E, Klopper A | title = The Urinary Excretion of Pregnanediol After the Administration of an Oral Gestagen (Progesterone Cyclopentyl Enol Ether) | journal = The Journal of Endocrinology | volume = 28 | issue = 2 | pages = 221–222 | date = January 1964 | pmid = 14112260 | doi = 10.1677/joe.0.0280221 | citeseerx = 10.1.1.1028.4921 }}</ref> The [bioavailability](/source/bioavailability) of quingestrone is highest when it is given as a [sesame seed oil](/source/sesame_seed_oil) solution (compared to an oil suspension (~2-fold less) or [micronization](/source/micronization) (~7-fold less)).<ref name="pmid18472981" />

The C3 enol ethers of progesterone are less suited for use via [depot injection](/source/depot_injection) relative to [progestogen ester](/source/progestogen_ester)s like [hydroxyprogesterone caproate](/source/hydroxyprogesterone_caproate) due to their susceptibility to [oxidative](/source/oxidation) [metabolism](/source/metabolism).<ref name="Junkmann1954">{{cite journal | vauthors = Junkmann K | title = Gestagens of prolonged action | journal = Naunyn-Schmiedebergs Archiv für Pharmakologie und Experimentelle Pathologie | volume = 223 | pages = 244–53 | year = 1954 | issn = 0365-5423 | quote = Among a large no. of pregnane derivs. the esters of 17-α-hydroxyprogesterone (I), itself of weak lutein hormone action, have a strong and long-lasting gestagen action. The optimal results are obtained with I caproate. It permits the administration of depot doses in clear solns. Within the range of dosage used no androgenic effect was noted. It has no influence on growth and on the secondary sex characteristics in infantile and adult castrate male rats. The 3-enol esters of progesterone, which have a somewhat prolonged action, are less suited for depot administration because of their oxidizability.}}</ref>

The [pharmacokinetics](/source/pharmacokinetics) of quingestrone have been reviewed.<ref name="Junkmann1968" />

==Chemistry==
{{See also|List of progestogens|Progestogen ester#Progestogen ethers|List of progestogen esters#Ethers of progesterone derivatives}}

Quingestrone, also known as progesterone 3-cyclopentyl enol ether (PCPE) or as 3-cyclopentyloxypregna-3,5-dien-20-one, is a [synthetic](/source/synthetic_compound) [pregnane](/source/pregnane) [steroid](/source/steroid) and a [derivative](/source/chemical_derivative) of [progesterone](/source/progesterone).<ref name="Elks2014" /> It is specifically the 3-[cyclopentyl](/source/cyclopentane) [enol ether](/source/enol_ether) of progesterone.<ref name="Elks2014" /> Quingestrone is closely related to [progesterone 3-acetyl enol ether](/source/progesterone_3-acetyl_enol_ether) and [pentagestrone acetate](/source/pentagestrone_acetate) (17α-acetoxyprogesterone 3-cyclopentyl enol ether).<ref name="Elks2014" />

===Synthesis===
[Chemical syntheses](/source/Chemical_synthesis) of quingestrone have been published.<ref name="Junkmann1968" />

==History==
Quingestrone appears to have been first [synthesized](/source/chemical_synthesis) in 1936.<ref name="Westphal1936">{{cite journal| vauthors = Westphal U |title=Über Enolacetate des Progesterons und Testosterons|journal=Die Naturwissenschaften|volume=24|issue=44|year=1936|pages=696–697|issn=0028-1042|doi=10.1007/BF01491541|bibcode=1936NW.....24..696W|s2cid=41442733}}</ref> It was introduced for medical use in [Italy](/source/Italy) by 1962.<ref name="CurrentMedicineAndDrugs1962" /><ref name="pmid13861933" />

==Society and culture==

===Generic names===
''Quingestrone'' is the [generic name](/source/generic_term) of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|USAN|United States Adopted Name}}.<ref name="Elks2014" /> It is also known by its developmental code name ''W-3399''.<ref name="Elks2014" />

===Brand names===
Quingestrone was marketed under the brand name Enol-Luteovis.<ref name="Elks2014" /><ref name="Micromedex" />

===Availability===
Quingestrone is no longer marketed and hence is no longer available in any country.<ref name="Micromedex">http://www.micromedexsolutions.com/micromedex2/ {{Dead link|date=February 2022}}</ref> It was previously available in [Italy](/source/Italy).<ref name="Micromedex" />

== References ==
{{Reflist}}

{{Progestogens and antiprogestogens}}
{{Navboxes
| title = [Pharmacodynamics](/source/Pharmacodynamics)
| titlestyle = background:#ccccff
| list1 = 
{{Glucocorticoid receptor modulators}}
{{Progesterone receptor modulators}}
{{Xenobiotic-sensing receptor modulators}}
}}

Category:Abandoned drugs
Category:Cyclopentyl ethers
Category:Conjugated dienes
Category:Ethers
Category:Glucocorticoids
Category:Hormonal contraception
Category:Ketones
Category:Pregnanes
Category:Progestogen ethers
Category:Progestogens

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