| Identification | Back Directory | [Name]
GW 842166X | [CAS]
666260-75-9 | [Synonyms]
CS-631
GW 842166
GW 842166X
GW842166X;GW 842166
GW842166X/GW-842166X
GW 842166X USP/EP/BP
2-(2,4-dichloroanilino)-N-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
2-(2,4-dichlorophenylamino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
2-(2,4-Dichlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid [(tetrahydropyran-4-yl)methyl]amide
5-Pyrimidinecarboxamide, 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C18H17Cl2F3N4O2 | [MDL Number]
MFCD11045840 | [MOL File]
666260-75-9.mol | [Molecular Weight]
449.25 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF:20.0(Max Conc. mg/mL);44.52(Max Conc. mM)
DMF:PBS (pH 7.2) (1:3):0.25(Max Conc. mg/mL);0.56(Max Conc. mM)
DMSO:37.77(Max Conc. mg/mL);84.07(Max Conc. mM)
Ethanol:0.3(Max Conc. mg/mL);0.67(Max Conc. mM) | [form ]
Powder | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
The peripheral cannabinoid (CB2) receptor is a G protein-coupled receptor (GPCR) that is localized predominantly in immune cells, monocytes, macrophages, and in several peripheral organs and binds the active component of cannabis, Δ9-tetrahydrocannabinol, as well as anandamide, an endogenous CB receptor ligand. GW 842166X is a peripheral cannabinoid (CB2) receptor agonist with ED50 values of 91 and 63 nM in rat and human, respectively. When administered orally to rats in the Freund’s complete adjuvant (FCA) model of inflammatory pain, GW 842166X is highly potent with an ED50 value of 0.1 mg/kg and full reversal of hyperalgesia at 0.3 mg/kg. | [Uses]
GW-842166X is pyrimidine ester based compound that is known as a highly selective CB2 receptor agonist for the treatment of inflammatory and neuropathic pain. | [Definition]
ChEBI: 5-pyrimidinecarboxamide, 2-[(2,4-dichlorophenyl)amino]-n-[(tetrahydro-2h-pyran-4-yl)methyl]-4-(trifluoromethyl)- is a dichlorobenzene. | [in vivo]
GW842166X has an oral ED50 of 0.1 mg/kg in the rat FCA model of inflammatory pain and shows full reversal of hyperalgesia at 0.3 mg/kg. The blood concentrations of GW842166X in experiments are 30 nM (0.03 mg/kg), 130 nM (0.1 mg/kg), and 370 nM (0.3 mg/ kg) 1 h after dosing. After dosing for 4 days in the FCA model, no statistical difference in antihyperalgesic response is observed on day 4 relative to day 1, indicating that tolerance does not occur[1]. | [storage]
Store at -20°C | [References]
[1] GERARD M. P. GIBLIN. Discovery of 2-[(2,4-Dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a Selective CB2 Receptor Agonist for the Treatment of Inflammatory Pain[J]. Journal of Medicinal Chemistry, 2007, 50 11: 2597-2600. DOI: 10.1021/jm061195+
[2] RACHEL RIBEIRO . Involvement of ERK1/2, cPLA2 and NF-κB in microglia suppression by cannabinoid receptor agonists and antagonists[J]. Prostaglandins & other lipid mediators, 2013, 100: Pages 1-14. DOI: 10.1016/j.prostaglandins.2012.11.003 |
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