GW-842,166X

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GW-842,166X
Identifiers
  • 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H17Cl2F3N4O2
Molar mass449.254 g/mol g·mol−1
3D model (JSmol)
  • C3COCCC3CNC(=O)c1cnc(nc1C(F)(F)F)Nc2ccc(Cl)cc2Cl
  • 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
  (verify)

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/S0065-7743(09)04411-X, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/S0065-7743(09)04411-X instead.