methylestradiol

Methylestradiol is used in combination with the progestin and androgen/anabolic steroid normethandrone (methylestrenolone) in the treatment of menopausal symptoms.

Methylestradiol is marketed in combination with normethandrone in the form of oral tablets containing 0.3 mg methylestradiol and 5 mg normethandrone.{{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.}}{{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 }}

Side effects of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding.

Methylestradiol is an estrogen, or an agonist of the estrogen receptor. It shows somewhat lower affinity for the estrogen receptor than estradiol or ethinylestradiol.

Methylestradiol is an active metabolite of the androgens/anabolic steroids methyltestosterone (17α-methyltestosterone), metandienone (17α-methyl-δ¹-testosterone), and normethandrone (17α-methyl-19-nortestosterone), and is responsible for their estrogenic side effects, such as gynecomastia and fluid retention.{{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–}}{{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 }}

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 relative to estradiol.{{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–}} This is analogous to the case of ethinylestradiol and its C17α ethynyl group.

{{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 estrane steroid and a derivative of estradiol. It is specifically the derivative of estradiol with a methyl group at the C17α positions. Closely related steroids include ethinylestradiol (17α-ethynylestradiol) and ethylestradiol (17α-ethylestradiol). The C3 cyclopentyl ether of methylestradiol has been studied and shows greater oral potency than methylestradiol in animals, similarly to quinestrol (ethinylestradiol 3-cyclopentyl ether) and quinestradol (estriol 3-cyclopentyl ether).{{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 }}

Methylestradiol was first marketed, alone as Follikosid and in combination with methyltestosterone as Klimanosid, in 1955.{{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 }}{{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–}}{{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}}{{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}}

Methylestradiol has not been assigned an {{abbrlink|INN|International Nonproprietary Name}} or other formal name designations. Its generic name in English and German is methylestradiol, in French is méthylestradiol, and in Spanish is metilestadiol. It is also known as 17α-methylestradiol.

Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination with normethandrone.

Methylestradiol is or has been marketed in Brazil, Venezuela, and Indonesia.

{{Reflist}}

{{Estrogens and antiestrogens}}

{{Estrogen receptor modulators}}

Category:Tertiary alcohols

Category:Estranes

Category:Human drug metabolites

Category:Synthetic estrogens