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GW-842,166X

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
GW-842,166X
Identifiers
  • 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H17Cl2F3N4O2
Molar mass449.26 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 selectivecannabinoidCB2receptoragonist, with a novel chemical structure based on apyrimidine core. It has potentanalgesic,anti-inflammatory andanti-hyperalgesic actions in animal models, but without cannabis-like behavioural effects due to its extremely low affinity for the CB1 receptor.[1][2] GSK brought this compound for into 4 clinical trials, two of them related to pain management[3][4] and the other two related to bio-distributions.[5][6] The trials were either withdrawn or completed without posting result.

See also

[edit]

References

[edit]
  1. ^Giblin GM, O'Shaughnessy CT, Naylor A, Mitchell WL, Eatherton AJ, Slingsby BP, et al. (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):2597–2600.doi:10.1021/jm061195+.PMID 17477516.
  2. ^Han S, Thatte J, Jones RM (2009).Chapter 11: Recent Advances in the Discovery of CB2 Selective Agonists. Annual Reports in Medicinal Chemistry. Vol. 44. pp. 227–246.doi:10.1016/S0065-7743(09)04411-X.ISBN 9780123747662.
  3. ^"Dose Response and Efficacy of GW842166 in Pain - Full Text View - ClinicalTrials.gov".clinicaltrials.gov. 12 February 2015. Retrieved2020-02-18.
  4. ^"Dental Pain 3rd Molar Tooth Extraction GW842166 - Full Text View - ClinicalTrials.gov".clinicaltrials.gov. 15 May 2009. Retrieved2020-02-18.
  5. ^"Relative Bioavailability Study on a Single Dose of GW842166X in Healthy Male and Female Subjects. - Full Text View - ClinicalTrials.gov".clinicaltrials.gov. 12 February 2015. Retrieved2020-02-18.
  6. ^"An Imaging Study to Investigate the Distribution of GW842166X in the Brain. - Full Text View - ClinicalTrials.gov".clinicaltrials.gov. 3 August 2017. Retrieved2020-02-18.
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