Dienestrol

{{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 =

|pregnancy_US =

|legal_AU =

|legal_UK =

|legal_US =

|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 nonsteroidal estrogen medication of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe.{{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–}}{{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–}}{{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–}}{{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–}} It has been studied for use by rectal administration in the treatment of prostate cancer in men as well.{{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 }} The medication was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene. Dienestrol is a close analogue of diethylstilbestrol.{{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]–}} It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.{{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 }}

Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.