SRT-2183

SRT-2183
Clinical data
ATC code	None;
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name N-[2-(3-{[(3R)-3-hydroxypyrrolidin-1-yl]methyl}imidazo[2,1-b][1,3]thiazol-6-yl)phenyl]naphthalene-2-carboxamide;
CAS Number	1001908-89-9 ;
PubChem CID	24180126;
ChemSpider	23315224 ;
UNII	6FKU9G9CX6;
ChEMBL	ChEMBL403308 ;
CompTox Dashboard (EPA)	DTXSID501029656 ;
Chemical and physical data
Formula	C27H24N4O2S
Molar mass	468.58 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccc2cc(ccc2c1)C(=O)Nc3ccccc3c4cn5c(csc5n4)CN6CC[C@H](C6)O;
	InChI InChI=1S/C27H24N4O2S/c32-22-11-12-30(15-22)14-21-17-34-27-29-25(16-31(21)27)23-7-3-4-8-24(23)28-26(33)20-10-9-18-5-1-2-6-19(18)13-20/h1-10,13,16-17,22,32H,11-12,14-15H2,(H,28,33)/t22-/m1/s1 ; Key:MUFSINOSQBMSLE-JOCHJYFZSA-N ;
	(verify)

SRT-2183 is a drug in development by Sirtris Pharmaceuticals intended as a small-molecule activator of the sirtuin subtype SIRT1. It has similar activity in animal studies to another SIRT1 activator SRT-1720, but is closer in potency to resveratrol. In animal studies it was found to improve insulin sensitivity and lower plasma glucose levels in fat, muscle and liver tissue, and increased mitochondrial and metabolic function.^[1] However, the claim that SRT-2183 is a SIRT1 activator has been questioned^[2] and further defended.^[3]

References

^ Milne JC, Lambert PD, Schenk S, Carney DP, Smith JJ, Gagne DJ, et al. (November 2007). "Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes". Nature. 450 (7170): 712–6. Bibcode:2007Natur.450..712M. doi:10.1038/nature06261. PMC 2753457. PMID 18046409.
^ Pacholec M, Bleasdale JE, Chrunyk B, Cunningham D, Flynn D, Garofalo RS, et al. (March 2010). "SRT1720, SRT2183, SRT1460, and resveratrol are not direct activators of SIRT1". The Journal of Biological Chemistry. 285 (11): 8340–51. doi:10.1074/jbc.M109.088682. PMC 2832984. PMID 20061378.
^ Dai H, Kustigian L, Carney D, Case A, Considine T, Hubbard BP, et al. (October 2010). "SIRT1 activation by small molecules: kinetic and biophysical evidence for direct interaction of enzyme and activator". The Journal of Biological Chemistry. 285 (43): 32695–703. doi:10.1074/jbc.M110.133892. PMC 2963390. PMID 20702418.

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Clinical data

ATC code	None
Legal status
Legal status	Investigational
Identifiers
IUPAC name N-[2-(3-{[(3R)-3-hydroxypyrrolidin-1-yl]methyl}imidazo[2,1-b][1,3]thiazol-6-yl)phenyl]naphthalene-2-carboxamide
CAS Number	1001908-89-9^Y
PubChem CID	24180126
ChemSpider	23315224^Y
UNII	6FKU9G9CX6
ChEMBL	ChEMBL403308^Y
CompTox Dashboard (EPA)	DTXSID501029656
Chemical and physical data
Formula	C₂₇H₂₄N₄O₂S
Molar mass	468.58 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1ccc2cc(ccc2c1)C(=O)Nc3ccccc3c4cn5c(csc5n4)CN6CC[C@H](C6)O
InChI InChI=1S/C27H24N4O2S/c32-22-11-12-30(15-22)14-21-17-34-27-29-25(16-31(21)27)23-7-3-4-8-24(23)28-26(33)20-10-9-18-5-1-2-6-19(18)13-20/h1-10,13,16-17,22,32H,11-12,14-15H2,(H,28,33)/t22-/m1/s1^Y Key:MUFSINOSQBMSLE-JOCHJYFZSA-N^Y
(verify)