Benzestrolのソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = 4,4'-(3-ethylhexane-2,4-diyl)diphenol
| image = Benzestrol.png
| width = 250px

<!--Clinical data-->
| tradename = Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| routes_of_administration = 
| class = [[Nonsteroidal estrogen]]

<!--Pharmacokinetic data-->
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<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 85-95-0
| CAS_supplemental = 
| ChEBI = 135264
| ChEMBL = 2104644
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A27512LR47
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 6827
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 6566
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<!--Chemical data-->
| C=20 | H=26 | O=2
| SMILES = CCC(C1=CC=C(C=C1)O)C(CC)C(C)C2=CC=C(C=C2)O
| StdInChI_Ref = 
| StdInChI = InChI=1S/C20H26O2/c1-4-19(14(3)15-6-10-17(21)11-7-15)20(5-2)16-8-12-18(22)13-9-16/h6-14,19-22H,4-5H2,1-3H3
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| StdInChIKey = DUTFBSAKKUNBAL-UHFFFAOYSA-N
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'''Benzestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}) (brand names '''Chemestrogen''', '''Ocestrol''', '''Octestrol''', '''Octoestrol''', '''Octofollin''') is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[stilbestrol]] group which was formerly used medically but has since been discontinued.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA133|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=133–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA47|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=47–}}</ref><ref>{{cite book | chapter = Benzestrol |title=Index Nominum 2000: International Drug Directory| chapter-url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA106|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=106–}}</ref> The stilbestrol estrogens, the best-known of which is [[diethylstilbestrol]] (DES) were used extensively in the mid-1900s and were finally banned by the FDA due to them causing tumors in the children of women who used them.<ref name="cdc">{{cite web | publisher = U.S. Centers for Disease Control and Prevention | title = DES History | url = https://www.cdc.gov/des/consumers/about/history.html | archive-url = https://web.archive.org/web/20190615144848/https://www.cdc.gov/des/consumers/about/history.html | archive-date = 15 June 2019 | access-date = 17 December 2012 }}</ref>

==Medical uses==
Benzestrol and other stilbestrol were used as synthetic estrogens in order to prevent premature births.<ref name="cdc" /> Based on the idea that premature births happened because the mother did not produce enough estrogen on her own, doctors prescribed benzestrol to mothers in order to increase their estrogen levels.

Studies have been done in the past on normal, mature and castrate female rats. Benzestrol produced the same type of estrus in the castrate rat when injected at 0.8 to 1.0 micrograms as when the rat was injected with 2.0 to 2.5 micrograms of estrone.<ref>{{cite journal |title=The Effects of a New Synthetic Estrogen, Benzestrol Upon the Hematopoietic System in the Rat| doi = 10.1210/endo-36-5-305 |year=1945 | vauthors = Stebbins RB, Blanchard EW |journal=Endocrinology |volume=36 |issue=5 |pages=305}}</ref> This is significant because less benzestrol could be used to produce the same effect as estrone in increasing estrogen production. It has been used in the past as a nonsteroidal estrogen antagonist.

==Pharmacology==

===Pharmacodynamics===
Benzestrol is described as a very potent estrogen.<ref>{{cite book | vauthors = Agarwal OP | chapter = Sex hormones |title=Natural Products|chapter-url=https://books.google.com/books?id=Zb84fVthd_cC&pg=PA288|year=2006|publisher=Krishna Prakashan Media|isbn=978-81-87224-85-3|pages=288–}}</ref> It is reported to have about 130% of the [[relative binding affinity]] of [[estradiol (medication)|estradiol]] for the [[estrogen receptor]]s.<ref name="pmid10099132">{{cite journal | vauthors = Fink BE, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA | title = Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens | journal = Chemistry & Biology | volume = 6 | issue = 4 | pages = 205–219 | date = April 1999 | pmid = 10099132 | doi = 10.1016/S1074-5521(99)80037-4 | doi-access = free }}</ref>

==Chemistry==
Benzestrol is usually grouped with the stilbestrol estrogens. However, benzestrol is technically not a stilbestrol derivative because its central chain is elongated by one carbon. In any case, it is a very close analogue of the stilbestrol estrogens.<ref name="Sevringhaus1944">{{cite journal| vauthors = Sevringhaus EL |title=Therapy of the Patient in the Menopause: Endocrine Methods|journal=The Journal of Clinical Endocrinology & Metabolism|volume=4|issue=12|year=1944|pages=597–604|issn=0021-972X|doi=10.1210/jcem-4-12-597}}</ref>

==History==
Benzestrol is a drug in the stilbestrol family of estrogens. These drugs were first produced in the late 1930s. Benzestrol itself was reported in 1946.<ref name="Elks2014" /> In 1953, experiments began on benzestrol and other stilbestrols to see if they actually helped stop premature births. This study in 1953 found that benzestrol did not in fact help stop premature births.<ref name="cdc" /> A study in 1971 found that benzestrol was the cause of a rare vaginal cancer in girls and women whose mothers had been on benzestrol while pregnant.<ref name="cdc" />

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

== References ==
{{Reflist|2}}

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

[[Category:Abandoned drugs]]
[[Category:Drugs acting on the blood and blood forming organs]]
[[Category:4-Hydroxyphenyl compounds]]
[[Category:Stilbenoids]]
[[Category:Synthetic estrogens]]