ERB-196のソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = 3-(3-Fluoro-4-hydroxyphenyl)-7-hydroxynaphthalene-1-carbonitrile
| image = ERB-196.svg
| width = 250px

<!--Clinical data-->
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| 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 -->
| legal_CA = 
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| legal_US = 
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| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 550997-55-2
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 470CL5L4AC
| ATC_prefix = 
| ATC_suffix = 
| ATC_supplemental = 
| PubChem = 6102691
| IUPHAR_ligand = 
| DrugBank_Ref = 
| DrugBank = DB06875
| ChemSpiderID_Ref = 
| ChemSpiderID = 4810213
| KEGG = 
| ChEBI = 
| ChEMBL = 192154
| synonyms = WAY-202196

<!--Chemical data-->
| C=17 | H=10 | F=1 | N=1 | O=2
| SMILES = C1(=CC2=C(C(=C1)C#N)C=C(C=C2)O)C1=CC(=C(C=C1)O)F
| StdInChI_Ref = 
| StdInChI = 1S/C17H10FNO2/c18-16-7-10(2-4-17(16)21)12-5-11-1-3-14(20)8-15(11)13(6-12)9-19/h1-8,20-21H
| StdInChIKey_Ref = 
| StdInChIKey = NSSOSHDCWCMNDM-UHFFFAOYSA-N
}}

'''ERB-196''', also known as '''WAY-202196''', is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] that acts as a highly [[binding selectivity|selective]] [[agonist]] of the [[ERβ]].<ref name="Hubbard2006">{{cite book| vauthors = Manas ES, MewshawRE, Harris HA, Malamas MS| chapter = Isoform Specificity: The Design of Estrogen Receptor-β Selective Compounds | veditors = Hubbard RE |title=Structure-based Drug Discovery: An Overview| chapter-url = https://books.google.com/books?id=Q_Kj1Qvgob4C&pg=PA241 |year=2006|publisher=Royal Society of Chemistry|isbn=978-0-85404-351-4|pages=241–}}</ref><ref name="AdisInsight">{{cite web |url=https://adisinsight.springer.com/drugs/800021229 |title=ERB 196 | work = AdisInsight | publisher = Springer Nature Switzerland AG |access-date=15 January 2022 |archive-url=https://web.archive.org/web/20180625161018/https://adisinsight.springer.com/drugs/800021229 |archive-date=25 June 2018 |url-status=dead}}</ref><ref name="ScholarlyEditions2013">{{cite book | vauthors = Acton QA | chapter = Estradiol |title=Estrogens—Advances in Research and Application |date=2013 |publisher=ScholarlyEditions | chapter-url=https://books.google.com/books?id=NYW4rG83zrUC&pg=PA52|isbn=978-1-4816-8771-3|pages=52– }}</ref><ref name="OttowWeinmann2008">{{cite book| vauthors = Weatherman RV | chapter = Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen-Binding Receptors | veditors = Ottow E, Weinmann H |title=Nuclear Receptors as Drug Targets| series = Methods and Principles in Medicinal Chemistry |chapter-url=https://books.google.com/books?id=iATfLbPgRugC&pg=PA66|date=8 September 2008|publisher=John Wiley & Sons|isbn=978-3-527-62330-3|pages=66– | doi = 10.1002/9783527623297.ch3 }}</ref><ref name="pmid15943471">{{cite journal | vauthors = Mewshaw RE, Edsall RJ, Yang C, Manas ES, Xu ZB, Henderson RA, Keith JC, Harris HA | display-authors = 6 | title = ERbeta ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERbeta selectivity | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 12 | pages = 3953–3979 | date = June 2005 | pmid = 15943471 | doi = 10.1021/jm058173s }}</ref><ref name="pmid16755255">{{cite journal | vauthors = Cristofaro PA, Opal SM, Palardy JE, Parejo NA, Jhung J, Keith JC, Harris HA | title = WAY-202196, a selective estrogen receptor-beta agonist, protects against death in experimental septic shock | journal = Critical Care Medicine | volume = 34 | issue = 8 | pages = 2188–2193 | date = August 2006 | pmid = 16755255 | doi = 10.1097/01.CCM.0000227173.13497.56 | s2cid = 20876539 }}</ref> It possesses 78-fold selectivity for the ERβ over the [[ERα]].<ref name="Hubbard2006" /> The drug was under development by [[Wyeth]] for the treatment of [[inflammation]] and [[sepsis]] starting in 2004 but development was discontinued by 2011.<ref name="AdisInsight" /><ref name="Vincent2007">{{cite book| vauthors = Adrie C, Azoulay E, Timsit JF | chapter = Influence of Gender on Outcome of Severe Sepsis | veditors = Vincent JL |title=Yearbook of Intensive Care and Emergency Medicine 2007| chapter-url = https://books.google.com/books?id=zT8_AAAAQBAJ&pg=PA891 |date=8 December 2007|publisher=Springer Science & Business Media|isbn=978-3-540-49433-1|pages=891–}}</ref>

== See also ==
* [[8β-VE2]]
* [[Diarylpropionitrile]]
* [[FERb 033]]
* [[Prinaberel]]
* [[WAY-166818]]
* [[WAY-200070]]
* [[WAY-214156]]

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

== External links ==
* [https://web.archive.org/web/20180625161018/https://adisinsight.springer.com/drugs/800021229 ERB-196 - AdisInsight]

{{Estrogen receptor modulators}}

[[Category:Hydroxyarenes]]
[[Category:Fluoroarenes]]
[[Category:Naphthalenes]]
[[Category:Nitriles]]
[[Category:Selective ERβ agonists]]
[[Category:Synthetic estrogens]]


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