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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = 8β-Vinylestra-1,3,5(10)-triene-3,17β-diol
| image = 8-vinylestradiol_structure.png
| width = 250px


| tradename =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
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| legal_US =
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| routes_of_administration =


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 367929-02-0
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem =
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 8007830
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = D5KU4JGS7Y
| KEGG =
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| ChEMBL =
| synonyms = 8β-Vinylestradiol; 8β-Vinylestra-1,3,5(10)-triene-3β,17β-diol


| C=20 | H=26 | O=2
| SMILES = C=C[C@@]12CCC3=CC(O)=CC=C3[C@@]1([H])CC[C@]4([C@@]2([H])CC[C@]4([H])O)C
| StdInChI_Ref =
| StdInChI = 1S/C20H26O2/c1-3-20-11-8-13-12-14(21)4-5-15(13)16(20)9-10-19(2)17(20)6-7-18(19)22/h3-5,12,16-18,21-22H,1,6-11H2,2H3/t16-,17-,18+,19+,20-/m1/s1
| StdInChIKey_Ref =
| StdInChIKey = NMCRWZRLOOYKTG-SWBPCFCJSA-N
}}

'''8β-VE2''', or '''8β-vinylestradiol''', also known as '''8β-vinylestra-1,3,5(10)-triene-3β,17β-diol''', is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] featuring an [[estradiol (medication)|estradiol]] core.<ref name="Shaw2009">{{cite book | vauthors = Pakdel F, Kah O, Jégou B | chapter = Mechanisms of action of particular endocrine-disrupting chemicals | veditors = Shaw I |title=Endocrine-Disrupting Chemicals in Food| chapter-url = https://books.google.com/books?id=x6ejAgAAQBAJ&pg=PA550|date=31 March 2009|publisher=Elsevier|isbn=978-1-84569-574-3|pages=550–}}</ref><ref name="pmid15037755">{{cite journal | vauthors = Hegele-Hartung C, Siebel P, Peters O, Kosemund D, Müller G, Hillisch A, Walter A, Kraetzschmar J, Fritzemeier KH | display-authors = 6 | title = Impact of isotype-selective estrogen receptor agonists on ovarian function | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 101 | issue = 14 | pages = 5129–5134 | date = April 2004 | pmid = 15037755 | pmc = 387385 | doi = 10.1073/pnas.0306720101 | doi-access = free | bibcode = 2004PNAS..101.5129H }}</ref> It is a highly [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[agonist]] of the [[ERβ]] that is used in [[scientific research]] to study the function of the ERβ.<ref name="Shaw2009" /><ref name="pmid15037755" /> It has 190-fold higher [[potency (pharmacology)|potency]] in [[transactivation]] [[bioassay|assay]]s of the ERβ relative to the [[ERα]] and 93- (rat) and 180-fold (human) preference in [[binding affinity]] for the ERβ over the ERα.<ref name="pmid15037755" />

In rodents, 8β-VE2 stimulates follicular growth and to a comparable extent as estradiol, whereas the highly ERα-selective agonist [[16α-LE2]] has no effect on [[ovarian follicle]] development, indicating that the ERβ and not the ERα is involved in the effects of estrogen on ovarian follicles.<ref name="pmid15037755" /><ref name="PlantZeleznik2014">{{cite book | vauthors = Binder K, Winuthayanon W, Hewitt SC, Couse JF, Korach KS | chapter = Steroid Receptors in the Uterus and Ovary| veditors = Plant TM, Zeleznik AJ |title=Knobil and Neill's Physiology of Reproduction| chapter-url = https://books.google.com/books?id=I1ACBAAAQBAJ&pg=PA1150|date=15 November 2014|publisher=Academic Press|isbn=978-0-12-397769-4|pages=1150–}}</ref> In contrast, 16α-LE2 stimulates [[uterus|uterine]] weight, whereas 8β-VE2 has no effect, indicating that the ERα and not the ERβ is involved in the effects of estrogen on the uterus.<ref name="pmid15037755" />

Research has determined through experimental [[animal testing on rodents|rodent studies]] with estradiol, 16α-LE2, and 8β-VE2 that the positive, protective effects of estrogens on [[bone formation]] [[bone resorption|resorption]] and [[bone mineral density]] are mediated via the ERα, whereas the ERβ does not appear to be involved.<ref name="pmid18433985">{{cite journal | vauthors = Hertrampf T, Schleipen B, Velders M, Laudenbach U, Fritzemeier KH, Diel P | title = Estrogen receptor subtype-specific effects on markers of bone homeostasis | journal = Molecular and Cellular Endocrinology | volume = 291 | issue = 1–2 | pages = 104–108 | date = September 2008 | pmid = 18433985 | doi = 10.1016/j.mce.2008.03.003 | s2cid = 1774519 | url = https://hal.archives-ouvertes.fr/hal-00532015/file/PEER_stage2_10.1016%252Fj.mce.2008.03.003.pdf }}</ref> On the other hand, while both ERα and ERβ are expressed in [[skeletal muscle]], it was found that ERβ is the predominant ER subtype that is responsible for estrogen stimulation of skeletal muscle growth and regeneration.<ref name="pmid22278942">{{cite journal | vauthors = Velders M, Schleipen B, Fritzemeier KH, Zierau O, Diel P | title = Selective estrogen receptor-β activation stimulates skeletal muscle growth and regeneration | journal = FASEB Journal | volume = 26 | issue = 5 | pages = 1909–1920 | date = May 2012 | pmid = 22278942 | doi = 10.1096/fj.11-194779 | doi-access = free | s2cid = 39692168 }}</ref> Moreover, similarly to [[testosterone]], 8β-VE2 has [[anabolic]] effects in skeletal muscle and significantly increases muscle mass as well as produces [[muscle hypertrophy]] in rats.<ref name="pmid22278942" /> In contrast to testosterone however, 8β-VE2 shows no [[androgenic]] effects.<ref name="pmid22278942" /> The effects of 8β-VE2 and ERβ may be mediated, in part, by local stimulation of [[insulin-like growth factor 1]] (IGF-1)-induced [[myogenesis|myogenic]] [[protein synthesis]], as 8β-VE2 has been found to strongly induce expression of IGF-1 in the rat [[levator ani]] muscle.<ref name="pmid22278942" />

== See also ==
* [[Diarylpropionitrile]]
* [[ERB-196]]
* [[Erteberel]]
* [[FERb 033]]
* [[Prinaberel]]
* [[WAY-166818]]
* [[WAY-200070]]
* [[WAY-214156]]

== References ==
{{Reflist}}

{{Estrogen receptor modulators}}

[[Category:Estranes]]
[[Category:Selective ERβ agonists]]
[[Category:Synthetic estrogens]]
[[Category:Vinyl compounds]]

8β-VE2 - 版の履歴

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WikiSysop: 1版をインポートしました