Dienestrol: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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|verifiedrevid = 460784619 |
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|IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol |
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|image = Dienestrol.svg |
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|width = 250px |
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|tradename = Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol |
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|Drugs.com = {{drugs.com|CONS|dienestrol}} |
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|pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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|pregnancy_US = <!-- A / B / C / D / X --> |
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|legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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|legal_UK = <!-- GSL / P / POM / CD --> |
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|legal_US = <!-- OTC / Rx-only --> |
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|class = [[Nonsteroidal estrogen]] |
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|IUPHAR_ligand = 7160 |
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|CAS_number_Ref = {{cascite|changed|CAS}} |
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|CAS_number = 13029-44-2 |
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|ATC_prefix = G03 |
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|ATC_suffix = CB01 |
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|ATC_supplemental = {{ATC|G03|CC02}} |
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|PubChem = 667476 |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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|DrugBank = DB00890 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 580857 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = RRW32X4U1F |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = D00898 |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEBI = 4518 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 1018 |
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|synonyms = Dienoestrol; ''p''-[(''E'',''E'')-1-Ethylidene-2-(''p''-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(''para''-hydroxyphenyl)-2,4-hexadiene |
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|C=18 | H=18 | O=2 |
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|SMILES = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|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+ |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = NFDFQCUYFHCNBW-SCGPFSFSSA-N |
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}} |
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'''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> |
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[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.<ref name="Elks2014" /> |
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<!--Clinical data--> |
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==Isomers== |
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| tradename = |
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<gallery> |
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| Drugs.com = {{drugs.com|CONS|dienestrol}} |
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Dienestrol structure.svg|Dienestrol (unspecified) - CAS [https://commonchemistry.cas.org/detail?ref=84-17-3 84-17-3] |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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E,E-Dienestrol structure.svg|''E'',''E''-Dienestrol - CAS [https://commonchemistry.cas.org/detail?ref=13029-44-2 13029-44-2] |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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Z,Z-Dienestrol structure.svg|''Z'',''Z''-Dienestrol - CAS [https://commonchemistry.cas.org/detail?ref=35495-11-5 35495-11-5] |
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| pregnancy_category = |
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</gallery> |
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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| legal_UK = <!-- GSL / P / POM / CD --> |
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| legal_US = <!-- OTC / Rx-only --> |
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| legal_status = |
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| routes_of_administration = |
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==See also== |
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<!--Pharmacokinetic data--> |
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* [[Benzestrol]] |
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| bioavailability = |
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* [[Hexestrol]] |
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| protein_bound = 50 to 80% |
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* [[Methestrol]] |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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==Notes== |
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<!--Identifiers--> |
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{{notelist}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 84-17-3 |
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| ATC_prefix = G03 |
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| ATC_suffix = CB01 |
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| ATC_supplemental = {{ATC|G03|CC02}} |
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| PubChem = 667476 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00890 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 580857 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RRW32X4U1F |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00898 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1018 |
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==References== |
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<!--Chemical data--> |
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{{Reflist}} |
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| C=18 | H=18 | O=2 |
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| molecular_weight = 266.334 g/mol |
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| smiles = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2 |
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| InChI = 1/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+ |
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| InChIKey = NFDFQCUYFHCNBW-SCGPFSFSBL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NFDFQCUYFHCNBW-SCGPFSFSSA-N |
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}} |
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'''Dienestrol''' is a synthetic [[estrogen]]. |
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==Synthesis== |
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[[File:Dienestrol.png|center|thumb|700px|Dienestrol synthesis:<ref>{{Cite doi|10.1098/rspb.1939.0015}}</ref>]] |
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#[[Pinacol coupling]] of the substituted [[propiophenone]]. |
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#[[Dehydration]] of the thus-obtained [[glycol]] with a mixture of [[acetyl chloride]] and [[acetic anhydride]] leads to the [[wikt:transoid|transoid]] [[diene]] system ([[bis]]-''β''-Methyl[[styrene]]-type). |
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#[[Saponification]] removes the acetate groups and thus affords dienestrol. |
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{{Estrogens and antiestrogens}} |
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==[[Hexestrol]]== |
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{{Estrogen receptor modulators}} |
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[[File:Hexestrol synthesis.svg|thumb|center|700px|[[Hexestrol]] synthesis:<ref>{{Cite doi|10.1098/rspb.1940.0009}}</ref><ref>{{Cite doi|10.1021/ja01867a067}}</ref><ref>{{Cite doi|10.1021/jo01158a010}}</ref> {{US patent|2357985}} {{Cite patent|GB|523320}}]] |
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[[Category:Abandoned drugs]] |
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The [[addition reaction]] of [[hydrogen bromide|HBr]] to [[anethole]] yields 1-bromo-1-(''p''-[[wikt:anisyl|anisyl]])propane. This is the subject of a [[Wurtz coupling]] reaction in the presence of sodium, magnesium, aluminium, or iron. Subsequent removal of the methoxy groups in the resulting dimerization product using [[hydroiodic acid]] gives hexestrol. |
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[[Category:Phenols]] |
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[[Category:Stilbenoids]] |
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==See also== |
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*[[Diethylstilbestrol]] |
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==References== |
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{{reflist}} |
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{{Estrogenics}} |
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[[Category:Synthetic estrogens]] |
[[Category:Synthetic estrogens]] |
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[[Category:Phenols]] |
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{{ |
{{Genito-urinary-drug-stub}} |
Latest revision as of 13:12, 13 December 2023
Clinical data | |
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Trade names | Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol |
Other names | Dienoestrol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(para-hydroxyphenyl)-2,4-hexadiene |
AHFS/Drugs.com | Micromedex Detailed Consumer Information |
Drug class | Nonsteroidal estrogen |
ATC code | |
Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.001.381 |
Chemical and physical data | |
Formula | C18H18O2 |
Molar mass | 266.340 g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
Dienestrol (INN , USAN ) (brand names Dienoestrol, Denestrolin, Dienol and many others[a]), also known as dienoestrol (BAN ), 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.[1][2][3][4] It has been studied for use by rectal administration in the treatment of prostate cancer in men as well.[5] The medication was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene.[4] Dienestrol is a close analogue of diethylstilbestrol.[6] It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.[7]
Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.[2]
Isomers[edit]
-
Dienestrol (unspecified) - CAS 84-17-3
-
E,E-Dienestrol - CAS 13029-44-2
-
Z,Z-Dienestrol - CAS 35495-11-5
See also[edit]
Notes[edit]
- ^ Other trade names of the medication include Ortho Dienestrol, Dienoestrol Ortho, Sexadien, Dinovex, Follormon, Oestrodiene, and Synestrol
References[edit]
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1.
- ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 390–. ISBN 978-1-4757-2085-3.
- ^ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5.
- ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3.
- ^ Sambuelli M (1953). "Somministrazione degli estrogeni per via rettale nel carcinoma prostatico" [Rectal administration of estrogens in prostate carcinoma]. Minerva Urol (in Italian). 5 (1): 28–32. ISSN 0026-4989. PMID 13063334.
- ^ VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
- ^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. doi:10.1210/endo.138.3.4979. PMID 9048584.