Misplaced Pages

GW-842,166X

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Chemical compound Pharmaceutical compound
GW-842,166X
Identifiers
IUPAC name
  • 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H17Cl2F3N4O2
Molar mass449.26 g·mol
3D model (JSmol)
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
  (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. GSK brought this compound for into 4 clinical trials, two of them related to pain management and the other two related to bio-distributions. The trials were either withdrawn or completed without posting result.

References

  1. Giblin GM, O'Shaughnessy CT, Naylor A, Mitchell WL, Eatherton AJ, Slingsby BP, et al. (May 2007). "Discovery of 2--N--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. Retrieved 2020-02-18.
  4. "Dental Pain 3rd Molar Tooth Extraction GW842166 - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. 15 May 2009. Retrieved 2020-02-18.
  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. Retrieved 2020-02-18.
  6. "An Imaging Study to Investigate the Distribution of GW842166X in the Brain. - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. 3 August 2017. Retrieved 2020-02-18.
Cannabinoids
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Stub icon

This cannabinoid related article is a stub. You can help Misplaced Pages by expanding it.

Categories: