GW-842,166X

GW-842,166X
Identifiers
	IUPAC name 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide;
CAS Number	666260-75-9;
PubChem CID	10253143;
ChemSpider	8428629;
UNII	VL1I6P2DZ8;
ChEMBL	ChEMBL225411;
CompTox Dashboard (EPA)	DTXSID60216786 ;
Chemical and physical data
Formula	C18H17Cl2F3N4O2
Molar mass	449.26 g·mol−1
3D model (JSmol)	Interactive image;
	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.[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of them related to pain management[3][4] and the other two related to bio-distributions.[5][6] The trials were either withdrawn or completed without posting result.

References

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.
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. pp. 227–246. doi:10.1016/S0065-7743(09)04411-X. ISBN 9780123747662.
"Dose Response and Efficacy of GW842166 in Pain - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2020-02-18.
"Dental Pain 3rd Molar Tooth Extraction GW842166 - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2020-02-18.
"Relative Bioavailability Study on a Single Dose of GW842166X in Healthy Male and Female Subjects. - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2020-02-18.
"An Imaging Study to Investigate the Distribution of GW842166X in the Brain. - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2020-02-18.

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[pmid17477516-1] 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] 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. 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. Retrieved 2020-02-18.

[4] "Dental Pain 3rd Molar Tooth Extraction GW842166 - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. 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. Retrieved 2020-02-18.

[6] "An Imaging Study to Investigate the Distribution of GW842166X in the Brain. - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2020-02-18.