SB-228357

SB-228357

Identifiers
IUPAC name N-(3-fluoro-5-pyridin-3-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide
CAS Number	181629-93-6
PubChem CID	443390
ChemSpider	391619
UNII	5RDN2E8E97
KEGG	C11742
ChEBI	CHEBI:8979
ChEMBL	ChEMBL14276
CompTox Dashboard (EPA)	DTXSID9042621
Chemical and physical data
Formula	C22H17F4N3O2
Molar mass	431.391 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C2C(=C1)CCN2C(=O)NC3=CC(=CC(=C3)C4=CN=CC=C4)F)C(F)(F)F
InChI InChI=1S/C22H17F4N3O2/c1-31-20-9-13-4-6-29(19(13)11-18(20)22(24,25)26)21(30)28-17-8-15(7-16(23)10-17)14-3-2-5-27-12-14/h2-3,5,7-12H,4,6H2,1H3,(H,28,30) Key:RRJLJKRFFRZRAF-UHFFFAOYSA-N

SB-228357 is a drug which acts as a selective antagonist of the serotonin 5-HT_2B and 5-HT_2C receptors.[1][2]

It has antidepressant and anxiolytic effects in animal models[1][2] and inhibits 5-HT_2B mediated proliferation of cardiac fibroblasts.[3] It has also been found to reverse meta-chlorophenylpiperazine (mCPP)-induced hypolocomotion[2] and to attenuate haloperidol-induced catalepsy.[1]

The drug was under development by GlaxoSmithKline for the treatment of major depressive disorder and anxiety disorders.[4] It reached the preclinical research phase of development.[4] However, development of the drug was discontinued.[4]

See also

• RS-102221
• SB-242084
• SB-243213

References

1. Reavill C, Kettle A, Holland V, Riley G, Blackburn TP (February 1999). "Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist". Br J Pharmacol. 126 (3): 572–574. doi:10.1038/sj.bjp.0702350. PMC 1565856. PMID 10188965.
2. Bromidge SM, Dabbs S, Davies DT, Davies S, Duckworth DM, Forbes IT, et al. (March 2000). "Biarylcarbamoylindolines are novel and selective 5-HT(2C) receptor inverse agonists: identification of 5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a potential antidepressant/anxiolytic agent". Journal of Medicinal Chemistry. 43 (6): 1123–34. doi:10.1021/jm990388c. PMID 10737744.
3. Hutcheson JD, Ryzhova LM, Setola V, Merryman WD (November 2012). "5-HT(2B) antagonism arrests non-canonical TGF-β1-induced valvular myofibroblast differentiation". Journal of Molecular and Cellular Cardiology. 53 (5): 707–14. doi:10.1016/j.yjmcc.2012.08.012. PMC 3472096. PMID 22940605.
4. "SB 228357". AdisInsight. 18 January 2008. Retrieved 14 January 2025.