Dienestrol: Difference between revisions

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| IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; ''p''-[(''E,E'')-1-Ethylidene-2-(''p''-hydroxyphenyl)-2-butenyl]phenol
| IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; ''p''-[(''E,E'')-1-Ethylidene-2-(''p''-hydroxyphenyl)-2-butenyl]phenol
| image = Dienestrol.svg
| image = Dienestrol.svg
| width =


<!--Clinical data-->
<!--Clinical data-->
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| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =
| class = [[Nonsteroidal estrogen]]


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| C=18 | H=18 | O=2
| C=18 | H=18 | O=2
| molecular_weight = 266.334 g/mol
| molecular_weight = 266.334 g/mol
| smiles = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
| SMILES = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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+
| 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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}}
}}


'''Dienestrol''' ([[International Nonproprietary Name|INN]], [[United States Adopted Name|USAN]]) (brand names '''Ortho Dienestrol''', '''Dienoestrol''', '''Dienoestrol Ortho''', '''Sexadien''', '''Denestrolin''', '''Dienol''', '''Dinovex''', '''Follormon''', '''Oestrodiene''', '''Synestrol''', numerous others), also known as '''dienoestrol''' ([[British Approved Name|BAN]]), is a [[synthetic compound|synthetic]], [[nonsteroidal]] [[estrogen]] of the [[stilbestrol]] group 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 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://books.google.com/books?id=7PrzbzO-Q2AC&pg=PA233|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=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 | url = }}</ref>
'''Dienestrol''' ([[International Nonproprietary Name|INN]], [[United States Adopted Name|USAN]]) (brand names '''Ortho Dienestrol''', '''Dienoestrol''', '''Dienoestrol Ortho''', '''Sexadien''', '''Denestrolin''', '''Dienol''', '''Dinovex''', '''Follormon''', '''Oestrodiene''', '''Synestrol''', numerous others), also known as '''dienoestrol''' ([[British Approved Name|BAN]]), is a [[synthetic compound|synthetic]], [[nonsteroidal estrogen]] 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 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://books.google.com/books?id=7PrzbzO-Q2AC&pg=PA233|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=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 | url = }}</ref>


[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and is used medically.<ref name="Elks2014" />
[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and is used medically.<ref name="Elks2014" />

Revision as of 04:56, 13 November 2017

Dienestrol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Drug classNonsteroidal estrogen
ATC code
Pharmacokinetic data
Protein binding50 to 80%
Identifiers
  • 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.381 Edit this at Wikidata
Chemical and physical data
FormulaC18H18O2
Molar mass266.334 g/mol g·mol−1
3D model (JSmol)
  • Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
  • InChI=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+ checkY
  • Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dienestrol (INN, USAN) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others), also known as dienoestrol (BAN), is a synthetic, nonsteroidal estrogen of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe.[1][2][3][4] It 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.[5] It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.[6]

Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and is used medically.[2]

See also

References

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1.
  2. ^ 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.
  3. ^ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5.
  4. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3.
  5. ^ VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
  6. ^ 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.


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