ERB-196

ERB-196
Clinical data
Other names	WAY-202196
Identifiers
	IUPAC name 3-(3-Fluoro-4-hydroxyphenyl)-7-hydroxynaphthalene-1-carbonitrile;
CAS Number	550997-55-2;
PubChem CID	6102691;
DrugBank	DB06875;
ChemSpider	4810213;
UNII	470CL5L4AC;
ChEMBL	ChEMBL192154;
CompTox Dashboard (EPA)	DTXSID70422018 ;
Chemical and physical data
Formula	C17H10FNO2
Molar mass	279.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1(=CC2=C(C(=C1)C#N)C=C(C=C2)O)C1=CC(=C(C=C1)O)F;
	InChI InChI=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; Key:NSSOSHDCWCMNDM-UHFFFAOYSA-N;

ERB-196, also known as WAY-202196, is a synthetic nonsteroidal estrogen that acts as a highly selective agonist of the ERβ.^[1]^[2]^[3]^[4]^[5]^[6] It possesses 78-fold selectivity for the ERβ over the ERα.^[1] The drug was under development by Wyeth for the treatment of inflammation and sepsis starting in 2004 but development was discontinued by 2011.^[2]^[7]

^ ^a ^b Manas ES, MewshawRE, Harris HA, Malamas MS (2006). "Isoform Specificity: The Design of Estrogen Receptor-β Selective Compounds". In Hubbard RE (ed.). Structure-based Drug Discovery: An Overview. Royal Society of Chemistry. pp. 241–. ISBN 978-0-85404-351-4.
^ ^a ^b "ERB 196". AdisInsight. Springer Nature Switzerland AG. Archived from the original on 25 June 2018. Retrieved 15 January 2022.
^ Acton QA (2013). "Estradiol". Estrogens—Advances in Research and Application. ScholarlyEditions. pp. 52–. ISBN 978-1-4816-8771-3.
^ Weatherman RV (8 September 2008). "Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen-Binding Receptors". In Ottow E, Weinmann H (eds.). Nuclear Receptors as Drug Targets. Methods and Principles in Medicinal Chemistry. John Wiley & Sons. pp. 66–. doi:10.1002/9783527623297.ch3. ISBN 978-3-527-62330-3.
^ Mewshaw RE, Edsall RJ, Yang C, Manas ES, Xu ZB, Henderson RA, et al. (June 2005). "ERbeta ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERbeta selectivity". Journal of Medicinal Chemistry. 48 (12): 3953–3979. doi:10.1021/jm058173s. PMID 15943471.
^ Cristofaro PA, Opal SM, Palardy JE, Parejo NA, Jhung J, Keith JC, Harris HA (August 2006). "WAY-202196, a selective estrogen receptor-beta agonist, protects against death in experimental septic shock". Critical Care Medicine. 34 (8): 2188–2193. doi:10.1097/01.CCM.0000227173.13497.56. PMID 16755255. S2CID 20876539.
^ Adrie C, Azoulay E, Timsit JF (8 December 2007). "Influence of Gender on Outcome of Severe Sepsis". In Vincent JL (ed.). Yearbook of Intensive Care and Emergency Medicine 2007. Springer Science & Business Media. pp. 891–. ISBN 978-3-540-49433-1.

[Hubbard2006-1] Manas ES, MewshawRE, Harris HA, Malamas MS (2006). "Isoform Specificity: The Design of Estrogen Receptor-β Selective Compounds". In Hubbard RE (ed.). Structure-based Drug Discovery: An Overview. Royal Society of Chemistry. pp. 241–. ISBN 978-0-85404-351-4.

[AdisInsight-2] "ERB 196". AdisInsight. Springer Nature Switzerland AG. Archived from the original on 25 June 2018. Retrieved 15 January 2022.

[ScholarlyEditions2013-3] Acton QA (2013). "Estradiol". Estrogens—Advances in Research and Application. ScholarlyEditions. pp. 52–. ISBN 978-1-4816-8771-3.

[OttowWeinmann2008-4] Weatherman RV (8 September 2008). "Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen-Binding Receptors". In Ottow E, Weinmann H (eds.). Nuclear Receptors as Drug Targets. Methods and Principles in Medicinal Chemistry. John Wiley & Sons. pp. 66–. doi:10.1002/9783527623297.ch3. ISBN 978-3-527-62330-3.

[pmid15943471-5] Mewshaw RE, Edsall RJ, Yang C, Manas ES, Xu ZB, Henderson RA, et al. (June 2005). "ERbeta ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERbeta selectivity". Journal of Medicinal Chemistry. 48 (12): 3953–3979. doi:10.1021/jm058173s. PMID 15943471.

[pmid16755255-6] Cristofaro PA, Opal SM, Palardy JE, Parejo NA, Jhung J, Keith JC, Harris HA (August 2006). "WAY-202196, a selective estrogen receptor-beta agonist, protects against death in experimental septic shock". Critical Care Medicine. 34 (8): 2188–2193. doi:10.1097/01.CCM.0000227173.13497.56. PMID 16755255. S2CID 20876539.

[Vincent2007-7] Adrie C, Azoulay E, Timsit JF (8 December 2007). "Influence of Gender on Outcome of Severe Sepsis". In Vincent JL (ed.). Yearbook of Intensive Care and Emergency Medicine 2007. Springer Science & Business Media. pp. 891–. ISBN 978-3-540-49433-1.

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