192703-06-3

Basic information

• Product Name: SR 144528
• Synonyms: SR 144528
• CAS NO: 192703-06-3
• Molecular Formula: C29H34ClN3O
• Molecular Weight: 476.05276
• Mol File: 192703-06-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 627.699 °C at 760 mmHg
• Flash Point: 333.42 °C
• Appearance: /
• Density: 1.222 g/cm³
• Vapor Pressure: 1.14E-15mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 20 mg/ml, with warming).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: SR 144528(CAS DataBase Reference)
• NIST Chemistry Reference: SR 144528(192703-06-3)
• EPA Substance Registry System: SR 144528(192703-06-3)

Safety Data

• RTECS: UQ6276700
• Hazardous Substances Data: 192703-06-3(Hazardous Substances Data)

Usage

Description

SR 144528 is a cannabinoid (CB) receptor 2 inverse agonist with Ki values ranging from 0.3 to 5.6 nM. It is selective for CB2 over CB1 receptors, where it has Ki values ranging from 305 to >10,000 nM. SR 144528 blocks the inhibitory effects of CP 55,940 on forskolin-induced adenylyl cyclase activity in CHO cells expressing hCB2 (IC50 = 10 nM) but not in cells expressing hCB1 (IC50 = >10 μM). SR 144528 has 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.

Uses

Different sources of media describe the Uses of 192703-06-3 differently. You can refer to the following data:
1. SR144528 has been used as a cannabinoid CB2 receptor antagonist:to study its blocking effect on the anti-dyskinetic functionality of HU-308to study its effects on spontaneous excitatory postsynaptic currents (sEPSCs) from the globus pallidus neuronsto analyze its effect on the gastric emptying in rats
2. SR 144528 acts as a selective peripheral cannabinoid (CB2) receptor inverse agonist. Used in studies involving application of cannibis and anticancer drugs and multi-drug resistance (MDR) of the patie nt.
3. SR 144528 acts as a selective peripheral cannabinoid (CB2) receptor inverse agonist. Used in studies involving application of cannabis and anticancer drugs and multi-drug resistance (MDR) of the patient.

Biochem/physiol Actions

SR144528 is a potent and highly selective cannabinoid CB2 receptor inverse agonist. SR144528 exhibited a Ki of 0.6 nM at CB2 compared to 400 nM at the related CB1 receptor.

in vitro

sr 144528 displayed subnanomolar affinity for both the rat spleen and cloned human cb2 receptors and had a 700-fold lower affinity for both the rat brain and cloned human cb1 receptors. moreover, sr 144528 showed no affinity for more than 70 receptors, ion channels or enzymes tested. sr 144528 could antagonize the inhibitory effects of the cannabinoid receptor agonist cp 55,940 on forskolin-stimulated adenylyl cyclase activity in cell lines expressing the human cb2 receptor but not in cells expressing the human cb1. in addition, sr 144528 could selectively block the mitogen-activated protein kinase activity that was induced by cp 55,940 in cell lines expressing human cb2 while an ic50 value of more than 1 μm was observed in cells expressing human cb1 [1].

in vivo

animal study showed that oral administration of sr 144528 could totally displace the ex vivo [3h]-cp 55,940 binding to mouse spleen membranes with a long action duration. whereas, after the oral route sr 144528 did not interact with the cannabinoid receptor expressed in the mouse brain cb1 [1].

References

1) Rinaldi-Carmona et al. (1998), SR-144528, the first potent and selective antagonist of the CB2 cannabinoid receptor; J. Pharmacol. Exp. Ther., 284 644 2) Portier et al. (1999), SR-144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist; J. Pharmacol. Exp. Ther., 288 582

InChI:InChI=1/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1

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Relevant articles and documents

Tritiation of the cannabinoid receptor antagonist SR144528 involving lithium aluminum tritide reduction; assessment of the kinetic isotope effect by 3H-NMR

The cannabinoid receptor antagonist SR144528 was synthesized by an approach that enabled the incorporation of high specific activity tritium label while circumventing the lability of the target compound to catalytic hydrogenation. Lithium aluminum tritide