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{{Short description|Chemical compound}}
{{distinguish|7α-Methylestradiol}}
{{Infobox drug
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',17''S'')-13,17-dimethyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthrene-3,17-diol
| image = Methylestradiol.svg
| width = 250px
| image2 = Methylestradiol molecule ball.png
| width2 = 250px


| tradename = Ginecosid, Ginecoside, Mediol, Renodiol
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]<ref name="pmid13673847" />
| class = [[Estrogen (medication)|Estrogen]]


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref =
| CAS_number = 302-76-1
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| PubChem = 66413
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 59787
| UNII = 08IS5358PS
| KEGG = C14483
| ChEBI = 34179
| ChEMBL = 1627631
| synonyms = NSC-52245; 17α-Methylestradiol; 17α-ME; 17α-Methylestra-1,3,5(10)-triene-3,17β-diol


| C=19 | H=26 | O=2
| SMILES = CC12CCC3C(C1CCC2(C)O)CCC4=C3C=CC(=C4)O
| StdInChI = 1S/C19H26O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h4,6,11,15-17,20-21H,3,5,7-10H2,1-2H3/t15-,16-,17+,18+,19+/m1/s1
| StdInChIKey = JXQJDYXWHSVOEF-GFEQUFNTSA-N
}}

'''Methylestradiol''', sold under the brand names '''Ginecosid''', '''Ginecoside''', '''Mediol''', and '''Renodiol''', is an [[estrogen (medication)|estrogen]] medication which is used in the treatment of [[menopausal symptoms]].<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=PA898|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=898–}}</ref><ref name="Drugs.com">{{cite web | title = Methylestradiol | work = Drugs.com | url = https://www.drugs.com/international/methylestradiol.html | access-date = 2 January 2016}}</ref><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=PA389|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=389–}}</ref> It is formulated in combination with [[normethandrone]], a [[progestin]] and [[androgen]]/[[anabolic steroid]] medication.<ref name="Drugs.com" /><ref name="HumansOrganization2007" /> Methylestradiol is taken [[oral administration|by mouth]].<ref name="pmid13673847">{{cite journal | vauthors = Hegemann O | title = [Oral hormonal treatment with methylestrene-olone & methylestradiol as early pregnancy tests] | language = de | journal = Die Medizinische | volume = 4 | issue = 21 | pages = 1032–1033 | date = May 1959 | pmid = 13673847 }}</ref>


[[Side effect]]s of methylestradiol include [[nausea]], [[breast tension]], [[edema]], and [[breakthrough bleeding]] among others.<ref name="Wittlinger1980">{{cite book| vauthors = Wittlinger H |title=Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones |chapter=Clinical Effects of Estrogens |year=1980 |pages=67–71 |doi=10.1007/978-3-642-67568-3_10 |isbn=978-3-642-67570-6 }}</ref> It is an [[estrogen (medication)|estrogen]], or an [[agonist]] of the [[estrogen receptor]]s, the [[biological target]] of estrogens like [[estradiol]].<ref name="pmid359134" />


Methylestradiol is or has been marketed in [[Brazil]], [[Venezuela]], and [[Indonesia]].<ref name="Drugs.com" /> In addition to its use as a medication, methylestradiol has been studied for use as a [[radiopharmaceutical]] for the [[estrogen receptor]].<ref name="pmid6406650">{{cite journal | vauthors = Feenstra A, Vaalburg W, Nolten GM, Reiffers S, Talma AG, Wiegman T, van der Molen HD, Woldring MG | display-authors = 6 | title = Estrogen receptor binding radiopharmaceuticals: II. Tissue distribution of 17 alpha-methylestradiol in normal and tumor-bearing rats | journal = Journal of Nuclear Medicine | volume = 24 | issue = 6 | pages = 522–528 | date = June 1983 | pmid = 6406650 }}</ref>

==Medical uses==
Methylestradiol is used in combination with the progestin and androgen/anabolic steroid [[normethandrone]] (methylestrenolone) in the treatment of [[menopausal symptom]]s.<ref name="Drugs.com" /><ref name="HumansOrganization2007" />

===Available forms===
Methylestradiol is marketed in combination with [[normethandrone]] in the form of [[oral administration|oral]] [[tablet (pharmacy)|tablet]]s containing 0.3 mg methylestradiol and 5 mg normethandrone.<ref name="UnlistedDrugs1982">{{cite book |title=Unlisted Drugs |url=https://books.google.com/books?id=BhxtAAAAMAAJ |year=1982 |publisher=Pharmaceutical Section, Special Libraries Association. |quote=Batynid. C. Each dragee contains: normethandrone, 5 mg.; and methylestradiol, 0.3 mg. E. (Formerly) Gynaekosid. M. Boehringer Biochemia, Florence. A. Estrogenic; Rx of secondary amenorrhea. R. Notiz Med Farm 32;295, Nov-Dec 81.}}</ref><ref name="pmid5948541">{{cite journal | vauthors = Akingba JB, Ayodeji EA | title = Amenorrhea as a leading symptom of choriocarcinoma | journal = The Journal of Obstetrics and Gynaecology of the British Commonwealth | volume = 73 | issue = 1 | pages = 153–155 | date = February 1966 | pmid = 5948541 | doi = 10.1111/j.1471-0528.1966.tb05137.x | s2cid = 38008851 }}</ref>

==Side effects==
[[Side effect]]s of methylestradiol include [[nausea]], [[breast tension]], [[edema]], and [[breakthrough bleeding]].<ref name="Wittlinger1980" />

==Pharmacology==

===Pharmacodynamics===
Methylestradiol is an [[estrogen (medication)|estrogen]], or an [[agonist]] of the [[estrogen receptor]].<ref name="pmid359134" /> It shows somewhat lower [[affinity (pharmacology)|affinity]] for the estrogen receptor than [[estradiol (medication)|estradiol]] or [[ethinylestradiol]].<ref name="pmid359134" />

Methylestradiol is an [[active metabolite]] of the androgens/anabolic steroids [[methyltestosterone]] (17α-methyltestosterone), [[metandienone]] (17α-methyl-δ<sup>1</sup>-testosterone), and [[normethandrone]] (17α-methyl-19-nortestosterone), and is responsible for their [[estrogen (medication)|estrogen]]ic [[side effect]]s, such as [[gynecomastia]] and [[water retention (medicine)|fluid retention]].<ref name="ThiemeHemmersbach2009" /><ref name="Llewellyn2011">{{cite book| vauthors = Llewellyn W |title= Anabolics |url= https://books.google.com/books?id=afKLA-6wW0oC&pg=PT533 |year=2011 |publisher=Molecular Nutrition Llc |isbn=978-0-9828280-1-4 |pages=533–}}</ref><ref name="pmid1964199">{{cite journal | vauthors = Friedl KE | title = Reappraisal of the health risks associated with the use of high doses of oral and injectable androgenic steroids | journal = NIDA Research Monograph | volume = 102 | pages = 142–177 | year = 1990 | pmid = 1964199 }}</ref>

{| class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"
|+ class="nowrap" | Relative affinities (%) of methylestradiol 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}}
|-
| [[Estradiol (medication)|Estradiol]] || 2.6 || 7.9 || 100 || 0.6 || 0.13 || 8.7 || <0.1
|-
| [[Ethinylestradiol]] || 15–25 || 1–3 || 112 || 1–3 || <1 || ? || ?
|-
| Methylestradiol || 3–10, 15–25 || 1–3 || 67 || 1–3 || <1 || ? || ?
|-
| [[Methyltestosterone]] || 3 || 45, 100–125 || ? || 1–5 || ? || 5 || ?
|-
| [[Normethandrone]] || 100 || 146 || <0.1 || 1.5 || 0.6 || ? || ?
|- class="sortbottom"
| colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Sources:''' Values are percentages (%). Reference [[ligand (biochemistry)|ligand]]s (100%) were [[progesterone (medication)|progesterone]] for the {{abbrlink|PR|progesterone receptor}}, [[testosterone (medication)|testosterone]] for the {{abbrlink|AR|androgen receptor}}, [[estradiol (medication)|{{abbr|E2|estradiol}}]] for the {{abbrlink|ER|estrogen receptor}}, {{abbrlink|DEXA|dexamethasone}} for the {{abbrlink|GR|glucocorticoid receptor}}, [[aldosterone]] for the {{abbrlink|MR|mineralocorticoid receptor}}, {{abbrlink|DHT|dihydrotestosterone}} for {{abbrlink|SHBG|sex hormone-binding globulin}}, and [[hydrocortisone|cortisol]] for {{abbrlink|CBG|Corticosteroid-binding globulin}}. '''Sources:''' <ref name="RaynaudOjasoo1979">{{cite book| vauthors = Raynaud JP, Ojasoo T, Bouton MM, Philibert D |title=Drug Design|chapter=Receptor Binding as a Tool in the Development of New Bioactive Steroids|year=1979|pages=169–214|doi=10.1016/B978-0-12-060308-4.50010-X|isbn=9780120603084|chapter-url=https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169}}</ref><ref name="pmid359134">{{cite journal | vauthors = Ojasoo T, Raynaud JP | title = Unique steroid congeners for receptor studies | journal = Cancer Research | volume = 38 | issue = 11 Pt 2 | pages = 4186–4198 | date = November 1978 | pmid = 359134 | url = http://cancerres.aacrjournals.org/content/38/11_Part_2/4186.short }}</ref><ref name="pmid3695484">{{cite journal | vauthors = Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP | title = Towards the mapping of the progesterone and androgen receptors | journal = Journal of Steroid Biochemistry | volume = 27 | issue = 1–3 | pages = 255–269 | date = 1987 | pmid = 3695484 | doi = 10.1016/0022-4731(87)90317-7 }}</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>
|}

===Pharmacokinetics===
Due to the presence of its C17α [[methyl group]], methylestradiol cannot be deactivated by [[oxidation]] of the C17β [[hydroxyl group]], resulting in improved [[metabolic stability]] and [[potency (pharmacology)|potency]] relative to [[estradiol (medication)|estradiol]].<ref name="ThiemeHemmersbach2009">{{cite book| vauthors = Thieme D, Hemmersbach P |title=Doping in Sports|url=https://books.google.com/books?id=R-hIC-caIn8C&pg=PA470|date=18 December 2009|publisher=Springer Science & Business Media|isbn=978-3-540-79088-4|pages=470–}}</ref> This is analogous to the case of [[ethinylestradiol]] and its C17α [[ethynyl group]].<ref name="ThiemeHemmersbach2009" />

==Chemistry==
{{See also|List of estrogens}}

Methylestradiol, or 17α-methylestradiol (17α-ME), also known as 17α-methylestra-1,3,5(10)-triene-3,17β-diol, is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and a [[chemical derivative|derivative]] of [[estradiol (medication)|estradiol]].<ref name="Elks2014" /><ref name="Drugs.com" /> It is specifically the derivative of estradiol with a [[methyl group]] at the C17α positions.<ref name="Elks2014" /><ref name="Drugs.com" /> Closely related steroids include [[ethinylestradiol]] (17α-ethynylestradiol) and [[ethylestradiol]] (17α-ethylestradiol).<ref name="Elks2014" /> The C3 [[cyclopentyl]] [[ether]] of methylestradiol has been studied and shows greater [[oral administration|oral]] [[potency (pharmacology)|potency]] than methylestradiol in animals, similarly to [[quinestrol]] (ethinylestradiol 3-cyclopentyl ether) and [[quinestradol]] (estriol 3-cyclopentyl ether).<ref name="FalconiRossi1970">{{cite conference | vauthors = Falconi G, Rossi GL, Ercoli A | title = Quinestrol and other cyclopentyl ethers of estrogenic steroids: different rates of storage in body fat. | veditors = James VH | conference = Third International Congress on Hormonal Steroids, Hamburg | date = September 1970 | location = Amsterdam, Excerpta Medica | series = International Congress Series No. 210. | pages = 218–219 | url = https://www.popline.org/node/474468 | archive-url = https://web.archive.org/web/20180328165552/https://www.popline.org/node/474468 | archive-date = 28 March 2018 }}</ref>

==History==
Methylestradiol was first marketed, alone as Follikosid and in combination with [[methyltestosterone]] as Klimanosid, in 1955.<ref name="KlinischeWochenschrift1955">{{cite journal | title = Neue Spezialitäten | journal = Klinische Wochenschrift | volume = 33 | issue = 31–32 | year = 1955 | pages = 773–774 | issn = 0023-2173 | doi = 10.1007/BF01473523| s2cid = 1678069 }}</ref><ref name="Kahr2013">{{cite book| vauthors = Kahr H |title=Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur|url=https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA20|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-7091-5694-0|pages=20–}}</ref><ref name="ArendsZörnig2013">{{cite book| vauthors = Arends G, Zörnig H, Hager H, Frerichs G, Kern W |title=Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte |url= https://books.google.com/books?id=8bLwBgAAQBAJ&pg=PA1156 |date=14 December 2013|publisher=Springer-Verlag|isbn=978-3-662-36329-4|pages=1156–1157, 1164}}</ref><ref name="Helwig_1956">{{cite book| vauthors = Helwig B |title=Moderne Arzneimittel: eine Spezialitätenkunde nach Indikationsgebieten für Ärzte und Apotheker|url=https://books.google.com/books?id=cdfQAAAAMAAJ|year=1956|publisher=Wissenschaftliche Verlagsgesellschaft|page=240}}</ref>

==Society and culture==

===Generic names===
Methylestradiol has not been assigned an {{abbrlink|INN|International Nonproprietary Name}} or other formal name designations.<ref name="Elks2014" /><ref name="Drugs.com" /> Its [[generic term|generic name]] in [[English language|English]] and [[German language|German]] is ''methylestradiol'', in [[French language|French]] is ''méthylestradiol'', and in [[Spanish language|Spanish]] is ''metilestadiol''.<ref name="Drugs.com" /> It is also known as ''17α-methylestradiol''.<ref name="Drugs.com" />

===Brand names===
Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination with [[normethandrone]].<ref name="Drugs.com" /><ref name="Elks2014" />

===Availability===
Methylestradiol is or has been marketed in [[Brazil]], [[Venezuela]], and [[Indonesia]].<ref name="Drugs.com" />

== References ==
{{Reflist}}

{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Tertiary alcohols]]
[[Category:Estranes]]
[[Category:Human drug metabolites]]
[[Category:Synthetic estrogens]]

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bsd>Mazewaxie: WP:GENFIXES

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