Mestranolのソースを表示

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 462249106
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',17''R'')-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-17-ol
| image = Mestranol.svg
| width = 225px
| image2 = Mestranol molecule ball.png
| width2 = 250px

<!--Clinical data-->
| tradename = Enovid, Norinyl, Ortho-Novum, others
| Drugs.com = {{drugs.com|international|mestranol}}
| MedlinePlus = a601050
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status = Rx-only
| routes_of_administration = [[Oral administration|By mouth]]<ref name="MortonHall2012" />
| class = [[Estrogen (medication)|Estrogen]]; [[Estrogen ether]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = [[Ethinylestradiol]]
| elimination_half-life = Mestranol: 50 min<ref name="RunnebaumRabe2013" /><br />{{abbr|EE|Ethinylestradiol}}: 7–36 hours<ref name="HughesWaters2016" /><ref name="pmid2256522" /><ref name="pmid23375353" /><ref name="Shellenberger1986" />
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 72-33-3
| ATC_prefix = None
| ATC_suffix = 
| ATC_supplemental = 
| PubChem = 6291
| IUPHAR_ligand = 7087
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01357
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6054
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B2V233XGE7
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00575
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6784
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1201151
| synonyms = Ethinylestradiol 3-methyl ether; EEME; EE3ME; CB-8027; L-33355; RS-1044; 17α-Ethynylestradiol 3-methyl ether; 17α-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol

<!--Chemical data-->
| C=21 | H=26 | O=2
| SMILES = O(c1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IMSSROKUHAOUJS-MJCUULBUSA-N
}}
<!-- Definition and medical uses -->
'''Mestranol''', sold under the brand names '''Enovid''', '''Norinyl''', and '''Ortho-Novum''' among others, is an [[estrogen (medication)|estrogen]] medication which has been used in [[birth control pill]]s, [[menopausal hormone therapy]], and the treatment of [[menstrual disorder]]s.<ref name="MortonHall2012" /><ref name="Marks2010" /><ref name="Blum2013" /><ref name="Drugs.com" /> It is formulated in combination with a [[progestin]] and is not available alone.<ref name="Drugs.com" /> It is taken [[oral administration|by mouth]].<ref name="MortonHall2012" />

<!-- Side effects and mechanism -->
[[Side effect]]s of mestranol 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 |year=1980 |isbn=978-3-642-67570-6 |pages=67–71 |chapter=Clinical Effects of Estrogens |publisher=Springer |doi=10.1007/978-3-642-67568-3_10}}</ref> It is an [[estrogen (medication)|estrogen]], or an [[agonist]] of the [[estrogen receptor]]s, the [[biological target]] of estrogens like [[estradiol]].<ref name="Shoupe2007">{{Cite book | vauthors = Shoupe D |url=https://books.google.com/books?id=sczb0Tk_2IwC&pg=PA23 |title=The Handbook of Contraception: A Guide for Practical Management |date=7 November 2007 |publisher=Springer Science & Business Media |isbn=978-1-59745-150-5 |pages=23– |quote=EE is about 1.7 times as potent as the same weight of mestranol.}}</ref> Mestranol is a [[prodrug]] of [[ethinylestradiol]] in the body.<ref name="Shoupe2007" />

<!-- History, society, and culture -->
Mestranol was discovered in 1956 and was introduced for medical use in 1957.<ref name="Sneader2005" /><ref name="LentzLobo2012" /> It was the estrogen component in the first birth control pill.<ref name="Sneader2005" /><ref name="LentzLobo2012" /> In 1969, mestranol was replaced by ethinylestradiol in most birth control pills, although mestranol continues to be used in a few birth control pills even today.<ref name="Aronson2009" /><ref name="Drugs.com" /> Mestranol remains available only in a few countries, including the [[United States]], [[United Kingdom]], [[Japan]], and [[Chile]].<ref name="Drugs.com" />