N-{4-chloro-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide Chemical Properties

Boiling point:

539.7±50.0 °C(Predicted)

Density 

1.505

storage temp. 

-20°C

solubility 

DMSO: >20mg/mL

form 

solid

pka

8.24±0.30(Predicted)

color 

Light yellow to yellow

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

N-{4-chloro-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide Usage And Synthesis

Description

CPPHA is a positive allosteric modulator of metabotropic glutamate receptor 5 (mGluR5) that potentiates human and rat mGluR5 activation by glutamate, 3,5-DHPG , and quisqualate (EC₅₀s = 0.316-0.5 and 0.634-1.16 μM for human and rat mGluR5, respectively). It is selective for mGluR5 over other mGluRs but exhibits submicromolar activity at PDE6, δ- and κ-opioid receptors, and the ether-a-go-go related gene (ERG) potassium channel (K_is = 500, 352, 474, and 813 nM, respectively). CPPHA potentiates 3,5-DHPG-induced NMDA currents in CA1 pyramidal cells and the depolarization of rat subthalamic nucleus (STN) neurons.

Uses

CPPHA is potent and selective positive allosteric modulator (PAM) of the mGluR5 and mGluR1 (metabotropic glutamate receptor). CPPHA can potentiate responses of mGluR5 and mGluR1 to activation of these receptors. CPPHA is developed for the research of central nervous system disorders[1][2].

IC 50

mGlu5 Receptor

References

[1] O'Brien JA, et al. A novel selective allosteric modulator potentiates the activity of native metabotropic glutamate receptor subtype 5 in rat forebrain. J Pharmacol Exp Ther. 2004 May;309(2):568-77. DOI:10.1124/jpet.103.061747
[2] N-{4-Chloro-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide (CPPHA) acts through a novel site as a positive allosteric modulator of group 1 metabotropic glutamate receptors. Mol Pharmacol. 2008 Mar;73(3):909-18. DOI:10.1124/mol.107.040097
[3] Liu F, et al. The effect of mGlu5 receptor positive allosteric modulators on signaling molecules in brain slices. Eur J Pharmacol. 2006 May 1;536(3):262-8. DOI:10.1016/j.ejphar.2006.02.003
[4] Zhang Y, et al. Allosteric potentiators of metabotropic glutamate receptor subtype 5 have differential effects on different signaling pathways in cortical astrocytes. J Pharmacol Exp Ther. 2005 Dec;315(3):1212-9. DOI:10.1124/jpet.105.090308

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