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SA 57

Names

[ CAS No. ]:
1346169-63-8

[ Name ]:
SA 57

[Synonym ]:
2-(Methylamino)-2-oxoethyl 4-[2-(4-chlorophenyl)ethyl]-1-piperidinecarboxylate
1-Piperidinecarboxylic acid, 4-[2-(4-chlorophenyl)ethyl]-, 2-(methylamino)-2-oxoethyl ester

Biological Activity

[Description]:

SA57 is a potent, selective FAAH inhibitor with IC50s of 3.2 nM and 1.9 nM for mouse and human FAAH. SA57 also inhibits the 2-arachidonoylglycerol hydrolases MAGL (IC50s of 410 nM and 1.4 μM for mouse and human MAGL) and mouse α/β-hydrolase domain-containing protein 6 (mABHD6; IC50 of 850 nM), but not other brain serine hydrolases[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> MAGL
Signaling Pathways >> Metabolic Enzyme/Protease >> FAAH
Research Areas >> Neurological Disease
Signaling Pathways >> Neuronal Signaling >> FAAH

[Target]

IC50: 3.2 nM (Mouse FAAH) and 1.9 nM (Human FAAH); 410 nM (Mouse MAGL) and 1.4 μM (Human MAGL); 850 nM (Mouse ABHD6)[1]


[In Vitro]

O-Aryl carbamate and N-aryl urea inhibitors have been shown to irreversibly inhibit FAAH by carbamylation of the enzyme’s serine nucleophile. SA57 exhibits clear time-dependent inhibition of FAAH and MAGL, suggesting a covalent mechanism of inactivation, presumably through carbamylation of the active site serine nucleophiles of these enzymes[1].

[In Vivo]

SA57 (0.01-12.5 mg/kg; intraperitoneal injection; for 2 hours; C57Bl/6 mice) treatment shows distinct dose-responsive activity against brain serine hydrolases (FAAH, MAGL and ABHD6) in vivo[1]. Animal Model: C57Bl/6 mice[1] Dosage: 0.01 mg/kg, 0.05 mg/kg, 0.25 mg/kg, 1.25 mg/kg, 6.25 mg/kg, 12.5 mg/kg Administration: Intraperitoneal injection; for 2 hours Result: Showed distinct dose-responsive activity against brain serine hydrolases. Inhibited FAAH, MAGL and ABHD6 in vivo.

[References]

[1]. Niphakis MJ, et al. O-hydroxyacetamide carbamates as a highly potent and selective class of endocannabinoid hydrolase inhibitors. ACS Chem Neurosci. 2012 May 16;3(5):418-26.

[2]. Owens RA, et al. Discriminative Stimulus Properties of the Endocannabinoid Catabolic Enzyme Inhibitor SA-57 in Mice. J Pharmacol Exp Ther. 2016 Aug;358(2):306-14.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
512.1±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C17H23ClN2O3

[ Molecular Weight ]:
338.829

[ Flash Point ]:
263.5±24.6 °C

[ Exact Mass ]:
338.139709

[ LogP ]:
2.71

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.540

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds