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 an antagonist for the 5HT_2B and 5HT_2C receptors. It has antidepressant and anxiolytic effects in animal models,^[1]^[2] and inhibits 5-HT_2B mediated proliferation of cardiac fibroblasts.^[3]

References

^ Reavill C, Kettle A, Holland V, Riley G, Blackburn TP (February 1999). "Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist". British Journal of Pharmacology. 126 (3): 572–4. doi: 10.1038/sj.bjp.0702350. PMC 1565856. PMID 10188965.
^ 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.
^ 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.

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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