GW-842,166X

GW-842,166X

Systematic (IUPAC) name
2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
Identifiers
CAS Number	666260-75-9
PubChem	CID 10253143
ChemSpider	8428629
ChEMBL	CHEMBL225411
Chemical data
Formula	C18H17Cl2F3N4O2
Molar mass	449.254 g/mol
SMILES C3COCCC3CNC(=O)c1cnc(nc1C(F)(F)F)Nc2ccc(Cl)cc2Cl
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) Key:TWQYWUXBZHPIIV-UHFFFAOYSA-N
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GW-842,166X is a drug which acts as a potent and selective cannabinoid CB₂ receptor agonist, with a novel chemical structure based on a pyrimidine core. It has potent analgesic, anti-inflammatory and anti-hyperalgesic actions in animal models, but without cannabis-like behavioural effects due to its extremely low affinity for the CB₁ receptor.^[1][2][3]

References

1. Giblin GM, O'Shaughnessy CT, Naylor A, Mitchell WL, Eatherton AJ, Slingsby BP, Rawlings DA, Goldsmith P, Brown AJ, Haslam CP, Clayton NM, Wilson AW, Chessell IP, Wittington AR, Green R (May 2007). "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". Journal of Medicinal Chemistry 50 (11): 2597–600. doi:10.1021/jm061195+. PMID 17477516.
2. Giblin GM, Billinton A, Briggs M, Brown AJ, Chessell IP, Clayton NM, Eatherton AJ, Goldsmith P, Haslam C, Johnson MR, Mitchell WL, Naylor A, Perboni A, Slingsby BP, Wilson AW (October 2009). "Discovery of 1-[4-(3-chlorophenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a brain penetrant 5-azaindole CB2 agonist for the treatment of chronic pain". Journal of Medicinal Chemistry 52 (19): 5785–8. doi:10.1021/jm9009857. PMID 19743867.
3. Han, S.; Thatte, J.; Jones, R. M. (2009). "Chapter 11: Recent Advances in the Discovery of CB2 Selective Agonists". Annual Reports in Medicinal Chemistry 44: 227. doi:10.1016/S0065-7743(09)04411-X.