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them related to pain management^[3]^[4] and the other two related to bio-distributions.^[5]^[6] The trials were either withdrawn or completed without posting result.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, 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.
^ 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.
^ "Dose Response and Efficacy of GW842166 in Pain - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. 12 February 2015. Retrieved 2020-02-18.
^ "Dental Pain 3rd Molar Tooth Extraction GW842166 - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. 15 May 2009. 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. 12 February 2015. Retrieved 2020-02-18.
^ "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.

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[pmid17477516-1] 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. 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.

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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)