16α-LE2のソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
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| IUPAC_name = 3,17β-Dihydroxy-16α,21-epoxy-19-nor-17α-pregna-1,3,5(10)-trien-21-one
| image = 16aLE2_structure.png
| width = 250

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| CAS_number = 406483-39-4
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| ChemSpiderID = 8037946
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| UNII = Z7DNN9U8AE 
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<!--Chemical data-->
| C=20 | H=24 | O=4
| smiles = O=C1O[C@@]2([H])[C@]([C@@]3(C)CC[C@]4([H])C5=CC=C(C=C5CC[C@@]4([H])[C@]3([H])C2)O)(C1)O
| StdInChI_Ref = 
| StdInChI = InChI=1S/C20H24O4/c1-19-7-6-14-13-5-3-12(21)8-11(13)2-4-15(14)16(19)9-17-20(19,23)10-18(22)24-17/h3,5,8,14-17,21,23H,2,4,6-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20+/m1/s1
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| StdInChIKey = NLUGVTJBNRSIKH-UQZPWQSVSA-N
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'''16α-LE2''', or '''16α-lactone-estradiol''', also known as '''3,17β-dihydroxy-19-nor-17α-pregna-1,3,5-(10)-triene-21,16α-lactone''', is a [[synthetic compound|synthetic]], [[steroid]]al [[estrogen]] featuring an [[estradiol]] core. It is a highly potent and selective [[agonist]] of the [[ERα]] that is used in [[scientific research]] to study the function of the ERα.<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 has 265-fold higher [[potency (pharmacology)|potency]] in [[transactivation]] [[bioassay|assay]]s of the ERα relative to the [[ERβ]] and 70-fold preference in [[binding affinity]] for the ERα over the ERβ.<ref name="pmid15037755" />

In rodents, 16α-LE2 has no effect on [[ovarian follicle]] development, whereas the highly ERβ-selective agonist [[8β-VE2]] stimulates follicular growth and to a comparable extent as [[estradiol]], 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>

== See also ==
* [[ERA-45]]
* [[ERA-63]]
* [[Propylpyrazoletriol]]
* [[Methylpiperidinopyrazole]]
* [[GTx-758]]
* [[Diarylpropionitrile]]
* [[WAY-200070]]
* [[16α-Iodo-E2]]

== References ==
{{reflist|30em}}

{{Estrogen receptor modulators}}

[[Category:Estranes]]
[[Category:Lactones]]
[[Category:Synthetic estrogens]]

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{{genito-urinary-drug-stub}}