Methylestradiolのソースを表示

{{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

<!--Clinical data-->
| tradename = Ginecosid, Ginecoside, Mediol, Renodiol
| 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 = 
| routes_of_administration = [[Oral administration|By mouth]]<ref name="pmid13673847" />
| class = [[Estrogen (medication)|Estrogen]]

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

<!--Identifiers-->
| 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

<!--Chemical data-->
| 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
}}
<!-- Definition and medical uses -->
'''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 effects and mechanism -->
[[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" />

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