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Dienestrol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dienestrol
Clinical data
Trade namesOrtho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol
Other namesDienoestrol;p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(para-hydroxyphenyl)-2,4-hexadiene
AHFS/Drugs.comMicromedex Detailed Consumer Information
Drug classNonsteroidal estrogen
ATC code
Identifiers
  • 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.381Edit this at Wikidata
Chemical and physical data
FormulaC18H18O2
Molar mass266.340 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 (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name) (brand namesDienoestrol,Denestrolin,Dienol and many others[a]), also known asdienoestrol (BANTooltip British Approved Name), is asyntheticnonsteroidal estrogen medication of thestilbestrol group which is or was used to treatmenopausal symptoms in theUnited States andEurope.[1][2][3][4] It has been studied for use byrectal administration in the treatment ofprostate cancer in men as well.[5] The medication was introduced in the U.S. in 1947 bySchering asSynestrol and in France in 1948 asCycladiene.[4] Dienestrol is a closeanalogue ofdiethylstilbestrol.[6] It has approximately 223% and 404% of theaffinity ofestradiol at theERα andERβ, respectively.[7]

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

Isomers

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See also

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Notes

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  1. ^Other trade names of the medication includeOrtho Dienestrol,Dienoestrol Ortho,Sexadien,Dinovex,Follormon,Oestrodiene, andSynestrol

References

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  1. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–.ISBN 978-3-88763-075-1.
  2. ^abJ. 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. ^abWilliam Andrew Publishing (22 October 2013).Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–.ISBN 978-0-8155-1856-3.
  5. ^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.
  6. ^VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–.ISBN 978-0-08-086600-0.
  7. ^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.


Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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