SERBA-2のソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
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| IUPAC_name = (3a''R'',4''S'',9b''S'')-4-(4-Hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[''c'']chromen-8-ol
| image = SERBA-2.svg
| width = 250

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| 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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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 533884-10-5
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| PubChem = 9925763
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| ChemSpiderID_Ref = 
| ChemSpiderID = 8101398
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| ChEMBL = 216355

<!--Chemical data-->
| C=18 | H=18 | O=3
| SMILES = C1C[C@@H]2[C@H](C1)C3=C(C=CC(=C3)O)O[C@@H]2C4=CC=C(C=C4)O
| StdInChI_Ref = 
| StdInChI = 1S/C18H18O3/c19-12-6-4-11(5-7-12)18-15-3-1-2-14(15)16-10-13(20)8-9-17(16)21-18/h4-10,14-15,18-20H,1-3H2/t14-,15+,18+/m0/s1
| StdInChIKey_Ref = 
| StdInChIKey = XIESSJVMWNJCGZ-HDMKZQKVSA-N
| synonyms = (2''S'',3''R'',4''S'')-SERBA<ref name="pmid23713677" />
}}

'''SERBA-2''', short for '''selective estrogen receptor beta agonist-2''', is a [[synthetic compound|synthetic]], [[nonsteroidal]] [[estrogen]] which acts as a selective [[ERβ]] [[agonist]].<ref name="pmid17034120">{{cite journal | vauthors = Norman BH, Dodge JA, Richardson TI, Borromeo PS, Lugar CW, Jones SA, Chen K, Wang Y, Durst GL, Barr RJ, Montrose-Rafizadeh C, Osborne HE, Amos RM, Guo S, Boodhoo A, Krishnan V | title = Benzopyrans are selective estrogen receptor beta agonists with novel activity in models of benign prostatic hyperplasia | journal = J. Med. Chem. | volume = 49 | issue = 21 | pages = 6155–7 | year = 2006 | pmid = 17034120 | doi = 10.1021/jm060491j }}</ref><ref name="pmid19967775">{{cite journal | vauthors = Minutolo F, Macchia M, Katzenellenbogen BS, Katzenellenbogen JA | title = Estrogen receptor β ligands: recent advances and biomedical applications | journal = Med Res Rev | volume = 31 | issue = 3 | pages = 364–442 | year = 2011 | pmid = 19967775 | doi = 10.1002/med.20186 | s2cid = 3841877 }}</ref> For the [[ERα]] and ERβ, SERBA-2 has [[affinity (pharmacology)|affinities]] (K<sub>i</sub>) of 14.5&nbsp;nM and 1.54&nbsp;nM, [[efficacy|efficacies]] of 85% and 100%, and [[EC50|EC<sub>50</sub>]] values of 85&nbsp;nM and 3.61&nbsp;nM, respectively, demonstrating 9-fold [[binding selectivity]] and 11-fold [[functional selectivity]] for the ERβ over the ERα.<ref name="pmid17034120" /><ref name="pmid19967775" /><ref name="pmid20738246">{{cite journal | vauthors = Lóránd T, Vigh E, Garai J | title = Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: phytoestrogens and xenoestrogens | journal = Curr. Med. Chem. | volume = 17 | issue = 30 | pages = 3542–74 | year = 2010 | pmid = 20738246 | doi = 10.2174/092986710792927813}}</ref><ref name="pmid23713677">{{cite journal | vauthors = Paterni I, Bertini S, Granchi C, Macchia M, Minutolo F | title = Estrogen receptor ligands: a patent review update | journal = Expert Opin Ther Pat | volume = 23 | issue = 10 | pages = 1247–71 | year = 2013 | pmid = 23713677 | doi = 10.1517/13543776.2013.805206 | s2cid = 6259593 }}</ref> An [[enantiomer]] of SERBA-2, [[erteberel]] (SERBA-1), is more [[potency (pharmacology)|potent]] and selective in comparison and is under development for the treatment of [[schizophrenia]].<ref name="AdisInsight">{{cite web |url=https://adisinsight.springer.com/drugs/800031986 |title=Erteberel - AdisInsight |website=adisinsight.springer.com |access-date=15 January 2022 |archive-url=https://web.archive.org/web/20161231170122/https://adisinsight.springer.com/drugs/800031986 |archive-date=31 December 2016 |url-status=dead}}</ref><ref name="pmid17034120" /><ref name="pmid19967775" /><ref name="pmid23713677" />

==See also==
* [[8β-VE2]]
* [[Diarylpropionitrile]]
* [[ERB-196]]
* [[Prinaberel]]
* [[WAY-200070]]

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

{{Estrogen receptor modulators}}

[[Category:Benzopyrans]]
[[Category:Diols]]
[[Category:Selective ERβ agonists]]
[[Category:Synthetic estrogens]]
[[Category:Cyclopentanes]]


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