SERBA-2

SERBA-2
Clinical data
Other names	(2S,3R,4S)-SERBA[1]
Identifiers
	IUPAC name (3aR,4S,9bS)-4-(4-Hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol;
PubChem CID	9925763;
ChemSpider	8101398;
ChEMBL	ChEMBL216355;
Chemical and physical data
Formula	C18H18O3
Molar mass	282.339 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@@H]2[C@H](C1)C3=C(C=CC(=C3)O)O[C@@H]2C4=CC=C(C=C4)O;
	InChI InChI=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; Key:XIESSJVMWNJCGZ-HDMKZQKVSA-N;

SERBA-2, short for selective estrogen receptor beta agonist-2, is a synthetic, nonsteroidal estrogen which acts as a selective ERβ agonist.[2][3] For the ERα and ERβ, SERBA-2 has affinities (K_i) of 14.5 nM and 1.54 nM, efficacies of 85% and 100%, and EC₅₀ values of 85 nM and 3.61 nM, respectively, demonstrating 9-fold binding selectivity and 11-fold functional selectivity for the ERβ over the ERα.[2][3][4][1] An enantiomer of SERBA-2, erteberel (SERBA-1), is more potent and selective in comparison and is under development for the treatment of schizophrenia.[5][2][3][1]

References

Paterni I, Bertini S, Granchi C, Macchia M, Minutolo F (2013). "Estrogen receptor ligands: a patent review update". Expert Opin Ther Pat. 23 (10): 1247–71. doi:10.1517/13543776.2013.805206. PMID 23713677.
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 (2006). "Benzopyrans are selective estrogen receptor beta agonists with novel activity in models of benign prostatic hyperplasia". J. Med. Chem. 49 (21): 6155–7. doi:10.1021/jm060491j. PMID 17034120.
Minutolo F, Macchia M, Katzenellenbogen BS, Katzenellenbogen JA (2011). "Estrogen receptor β ligands: recent advances and biomedical applications". Med Res Rev. 31 (3): 364–442. doi:10.1002/med.20186. PMID 19967775.
Lóránd T, Vigh E, Garai J (2010). "Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: phytoestrogens and xenoestrogens". Curr. Med. Chem. 17 (30): 3542–74. doi:10.2174/092986710792927813. PMID 20738246.
https://adisinsight.springer.com/drugs/800031986%5B%5D

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[pmid23713677-1] Paterni I, Bertini S, Granchi C, Macchia M, Minutolo F (2013). "Estrogen receptor ligands: a patent review update". Expert Opin Ther Pat. 23 (10): 1247–71. doi:10.1517/13543776.2013.805206. PMID 23713677.

[pmid17034120-2] 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 (2006). "Benzopyrans are selective estrogen receptor beta agonists with novel activity in models of benign prostatic hyperplasia". J. Med. Chem. 49 (21): 6155–7. doi:10.1021/jm060491j. PMID 17034120.

[pmid19967775-3] Minutolo F, Macchia M, Katzenellenbogen BS, Katzenellenbogen JA (2011). "Estrogen receptor β ligands: recent advances and biomedical applications". Med Res Rev. 31 (3): 364–442. doi:10.1002/med.20186. PMID 19967775.

[pmid20738246-4] Lóránd T, Vigh E, Garai J (2010). "Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: phytoestrogens and xenoestrogens". Curr. Med. Chem. 17 (30): 3542–74. doi:10.2174/092986710792927813. PMID 20738246.

[AdisInsight-5] ttps://adisinsight.springer.com/drugs/800031986%5B%5D

SERBA-2

See also

References