SR 144528A cannabinoid receptor inverse agonist

SR 144528 (CAS 192703-06-3)

SR 144528 | CAS 192703-06-3 is rated 5.0 out of 5 by 1.
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Synonym: 5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1R,3S,4S)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide
Application: A cannabinoid receptor inverse agonist
CAS Number: 192703-06-3
Purity: ≥98%
Molecular Weight: 476.05
Molecular Formula: C29H34ClN3O
* Refer to Certificate of Analysis for lot specific data (including water content).
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SR 144528 is a selective peripheral CB2 (cannabinoid) receptor inverse agonist that displays a Ki value of 0.6 nM for rat spleen and human recombinant CB2 receptors and a Ki value of 400 nM for rat brain and human recombinant CB1 receptors. SR 144528 antagonizes the inhibitory effects of CP 55,940 on forskolin-induced adenylyl cyclase activity in CHO cells expressing hCB2. SR 144528 has also been used to investigate the contribution of the CB2 receptor in the control of pain initiation as well as suppression of inflammation and immune activation.


References

1 Rinaldi-Carmona, M., Barth, F., Millan, J., et al. SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J Pharmacol Exp Ther 284(2) 644-650 (1998). 2 Portier, M., Rinaldi-Carmona, M., Pecceu, F., et al. SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist. J Pharmacol Exp Ther 288(2) 582-589 (1999). 3 Barth, F., Rinaldi-Carmona, M. The development of cannabinoid antagonists. Current Medicinal Chemistry 6 745-755 (1999). 4 Di Marzo, V. Targeting the endocannabinoid system: To enhance or reduce?. Nature Reviews Drug Discovery 7 438-455 (2008). 5 Iwamura, H., Suzuki, H., Ueda, Y., et al. In vitro and in vivo pharmacological characterization of JTE-907, a novel selection ligand for cannabinoid CB2 receptor. J Pharmacol Exp Ther 296(2) 420-425 (2001). 6 Wright, K.L., Duncan, M., Sharkey, K.A. Cannabinoid CB2 receptors in the gastrointestinal tract: A regulatory system in states of inflammation. Br J Pharmacol 153 263-270 (2008).

Physical State :
Solid
Solubility :
Soluble in ethanol (~20 mg/ml), DMSO (~20 mg/ml), DMF (~20 mg/ml), and 1: 1 ethanol: PBS (pH 7.2) (~0.5 mg/ml).
Storage :
Store at -20° C
Melting Point :
272.59° C (Predicted)
Boiling Point :
~627.7° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.63 (Predicted)
IC50 :
Inhibitory effects of CP 55,940 on forskolin-induced adenylyl cyclase activity in CHO cells expressing hCB2: IC50 = 10 nM
Ki Data :
CB2: Ki= 0.6 nM; CB1: Ki= 121.2 nM (human)
pK Values :
pKa: 11.52 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
3081355
MDL Number :
MFCD05662316
SMILES :
CC1=CC=C(C=C1)CN2C(=CC(=N2)C(=O)N[C@H]3[C@]4(CC[C@H](C4)C3(C)C)C)C5=CC(=C(C=C5)Cl)C

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Certificate of Analysis

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SR 144528  Product Citations

See how others have used SR 144528. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 26890113  Deiana, V. et al. 2016. Eur J Med Chem. 112: 66-80.

PMID: # 26209834  Ragusa, G. et al. 2015. Eur J Med Chem. 101: 651-67.

PMID: # 26376816  Li, L. et al. 2015. Transl Stroke Res. 6: 467-77.

PMID: # 22595113  Miyashita, K. et al. 2012. J Endod. 38: 786-90.

Citations 1 to 4 of 4 total
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Rated 5 out of 5 by from Li Li, L. et al. (PubMed 26376816) used the cannabinoid receptor antagonist SR 144528 to demonstrate that cannabinoid receptor 2 activation prevents thrombin-induced blood-brain barrier damage via the inhibition of microglial activation and matrix metalloproteinase expression in rats. -SCBT Publication Review
Date published: 2015-02-04
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