GW842166XCAS# 666260-75-9 |
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Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
| Cas No. | 666260-75-9 | SDF | Download SDF |
| PubChem ID | 10253143 | Appearance | Powder |
| Formula | C18H17Cl2F3N4O2 | M.Wt | 449.25 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 83.3 mg/mL (185.42 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 2-(2,4-dichloroanilino)-N-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide | ||
| SMILES | C1COCCC1CNC(=O)C2=CN=C(N=C2C(F)(F)F)NC3=C(C=C(C=C3)Cl)Cl | ||
| Standard InChIKey | TWQYWUXBZHPIIV-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C18H17Cl2F3N4O2/c19-11-1-2-14(13(20)7-11)26-17-25-9-12(15(27-17)18(21,22)23)16(28)24-8-10-3-5-29-6-4-10/h1-2,7,9-10H,3-6,8H2,(H,24,28)(H,25,26,27) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | GW842166X is a potent and selective cannabinoid receptor 2 (CB2) agonist with IC50 values of 63 and 91 nM for human and rat CB2, respectively.In Vitro:GW842166X shows similar potency and efficacy for rat and human recombinant CB2 receptors. It has no significant agonist activity at concentrations up to 30 µM in human and rat CB1 recombinant assays[1].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]. References: | |||||
GW842166X Dilution Calculator
GW842166X Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2259 mL | 11.1297 mL | 22.2593 mL | 44.5186 mL | 55.6483 mL |
| 5 mM | 0.4452 mL | 2.2259 mL | 4.4519 mL | 8.9037 mL | 11.1297 mL |
| 10 mM | 0.2226 mL | 1.113 mL | 2.2259 mL | 4.4519 mL | 5.5648 mL |
| 50 mM | 0.0445 mL | 0.2226 mL | 0.4452 mL | 0.8904 mL | 1.113 mL |
| 100 mM | 0.0223 mL | 0.1113 mL | 0.2226 mL | 0.4452 mL | 0.5565 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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GW842166X is a potent and highly selective agonist of cannabinoid receptor CB2 receptor with EC50 of 63 nM, shows no significant activity at CB1 receptor. Phase 2.
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Developing pyridazine-3-carboxamides to be CB2 agonists: The design, synthesis, structure-activity relationships and docking studies.[Pubmed:28651225]
Eur J Med Chem. 2017 Sep 8;137:598-611.
Herein, we described the design and synthesis of a series of pyridazine-3-carboxamides to be CB2-selective agonists via a combination of scaffold hopping and bioisosterism strategies. The compounds were subjected to assessment of their potential activities through calcium mobilization assays. Among the tested derivatives, more than half of these compounds exhibited moderate to potent CB2 agonist activity. Six compounds showed EC50 values below 35 nM, and several derivatives also exhibited significantly enhanced potency and high selectivity at the CB2 receptor over the CB1 receptor. Specifically, compound 26 showed the highest CB2 agonist activity (EC50 = 3.665 +/- 0.553 nM) and remarkable selectivity (Selectivity Index > 2729) against CB1. In addition, logPs of some representative compounds were measured to display significantly decreased values in comparison with GW842166X. Furthermore, docking simulations were conducted to explain the interaction mode of this series.
Development of Quinazoline/Pyrimidine-2,4(1H,3H)-diones as Agonists of Cannabinoid Receptor Type 2.[Pubmed:28626532]
ACS Med Chem Lett. 2017 May 1;8(6):678-681.
Starting from a prototypical structure 1, we describe our efforts to design and obtain novel quinazoline/pyrimidine-2,4(1H,3H)-diones with high CB2 agonist potency and selectivity as well as improved physicochemical characteristics, mainly hydrophilicity. The most potent and selective CB2 agonists, 8 and 36, in this series were also endowed with lower logP values than that of GW842166X and lead compound 1. These derivatives appear to be promising lead compounds for the development of future CB2 agonists.
The agonist binding mechanism of human CB2 receptor studied by molecular dynamics simulation, free energy calculation and 3D-QSAR studies.[Pubmed:24358778]
Yao Xue Xue Bao. 2013 Sep;48(9):1436-49.
CB2-selective agonists have drawn attention in drug discovery, since CB2 becomes a promising target for the treatment of neuropathic pain without psychoactive or other CNS-related side effects. However, the lack of experimental data of the 3D structures of human cannabinoid receptors hampers the understanding of the binding modes between ligands and CB2 by traditional methods. In the present work, combinational molecular modeling studies including flexible docking, MD simulations and free energy calculations were performed to investigate the interaction modes and mechanism of CB2-unselective agonist CP55940 and CB2-selective agonist GW842166X, separately binding with the homology model of CB2 in a DPPC/TIP3P simulated membrane environment. The binding free energies calculated by MM-PBSA method give an explanation for the activity differences of the studied ligands. Binding free energies decomposition by MM-GBSA method shows that the van der Waals interaction is the dominant driving force during the binding process. Our MD simulations demonstrate that Phe197 could be a critical residue for the binding of CB2-selective agonists. Furthermore, by using the MD simulated binding conformer as a template, the 3D-QSAR studies were performed with the comparative molecular field analysis (CoMFA) approach on a set of GW842166X analogues. A combinational exploration of both CoMFA steric and potential contour maps for CB2 affinities and the MD studied interaction modes sheds light on the structural requirements for CB2 agonists and serves as a basis for the design of novel CB2 agonists.
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.[Pubmed:17477516]
J Med Chem. 2007 May 31;50(11):2597-600.
Selective CB2 receptor agonists are promising potential therapeutic agents for the treatment of inflammatory and neuropathic pain. A focused screen identified a pyrimidine ester as a partial agonist at the CB2 receptor with micromolar potency. Subsequent lead optimization identified 35, GW842166X, as the optimal compound in the series. 35 has an oral ED50 of 0.1 mg/kg in the rat FCA model of inflammatory pain and was selected as a clinical candidate for this indication.
