Dienestrolのソースを表示

{{Short description|Chemical compound}}
{{Drugbox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 460784619
|IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
|image = Dienestrol.svg
|width = 250px
|tradename = Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol
|Drugs.com = {{drugs.com|CONS|dienestrol}}
|pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
|pregnancy_US = <!-- A / B / C / D / X -->
|legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
|legal_UK = <!-- GSL / P / POM / CD -->
|legal_US = <!-- OTC / Rx-only -->
|class = [[Nonsteroidal estrogen]]
|IUPHAR_ligand = 7160
|CAS_number_Ref = {{cascite|changed|CAS}}
|CAS_number = 13029-44-2
|ATC_prefix = G03
|ATC_suffix = CB01
|ATC_supplemental = {{ATC|G03|CC02}}
|PubChem = 667476
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB00890
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 580857
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = RRW32X4U1F
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = D00898
|ChEBI_Ref = {{ebicite|changed|EBI}}
|ChEBI = 4518
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 1018
|synonyms = Dienoestrol; ''p''-[(''E'',''E'')-1-Ethylidene-2-(''p''-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(''para''-hydroxyphenyl)-2,4-hexadiene
|C=18 | H=18 | O=2
|SMILES = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = NFDFQCUYFHCNBW-SCGPFSFSSA-N
}}
'''Dienestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (brand names '''Dienoestrol''', '''Denestrolin''', '''Dienol''' and many others{{efn|Other trade names of the medication include '''Ortho Dienestrol''', '''Dienoestrol Ortho''', '''Sexadien''', '''Dinovex''', '''Follormon''', '''Oestrodiene''',  and '''Synestrol'''}}), also known as '''dienoestrol''' ({{abbrlink|BAN|British Approved Name}}), is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] medication of the [[stilbestrol]] group which is or was used to treat [[menopause|menopausal]] symptoms in the [[United States]] and [[Europe]].<ref>{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA331|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=331–}}</ref><ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA390|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=390–}}</ref><ref name="Muller1998">{{cite book|author=Muller|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA361|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=361–}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1286|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1286–}}</ref> It has been studied for use by [[rectal administration]] in the treatment of [[prostate cancer]] in men as well.<ref name="pmid13063334">{{cite journal | vauthors = Sambuelli M | title = Somministrazione degli estrogeni per via rettale nel carcinoma prostatico. | trans-title = Rectal administration of estrogens in prostate carcinoma | language = it | journal = Minerva Urol | volume = 5 | issue = 1 | pages = 28–32 | date = 1953 | issn = 0026-4989 | pmid = 13063334 }}</ref> The medication was introduced in the U.S. in 1947 by [[Schering AG|Schering]] as '''Synestrol''' and in France in 1948 as '''Cycladiene'''.<ref name="Publishing2013" /> Dienestrol is a close [[structural analog|analogue]] of [[diethylstilbestrol]].<ref>{{cite book|title=VITAMINS AND HORMONES|url=https://archive.org/details/in.ernet.dli.2015.5563|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=[https://archive.org/details/in.ernet.dli.2015.5563/page/n253 233]–}}</ref> It has approximately 223% and 404% of the [[affinity (pharmacology)|affinity]] of [[estradiol]] at the [[ERα]] and [[ERβ]], respectively.<ref name="pmid9048584">{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–70 | year = 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | doi-access = free }}</ref>

[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.<ref name="Elks2014" />
==Isomers==
<gallery>
Dienestrol structure.svg|Dienestrol (unspecified) - CAS [https://commonchemistry.cas.org/detail?ref=84-17-3  84-17-3]
E,E-Dienestrol structure.svg|''E'',''E''-Dienestrol - CAS [https://commonchemistry.cas.org/detail?ref=13029-44-2 13029-44-2]
Z,Z-Dienestrol structure.svg|''Z'',''Z''-Dienestrol - CAS [https://commonchemistry.cas.org/detail?ref=35495-11-5  35495-11-5]
</gallery>

==See also==
* [[Benzestrol]]
* [[Hexestrol]]
* [[Methestrol]]

==Notes==
{{notelist}}

==References==
{{Reflist}}


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

[[Category:Abandoned drugs]]
[[Category:4-Hydroxyphenyl compounds]]
[[Category:Stilbenoids]]
[[Category:Synthetic estrogens]]


{{Genito-urinary-drug-stub}}