GW-405,833

GW-405,833
Identifiers
	IUPAC name 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole;
CAS Number	180002-83-9 ;
PubChem CID	9911463;
ChemSpider	8087114 ;
UNII	85K154W99L;
ChEMBL	ChEMBL73711 ;
CompTox Dashboard (EPA)	DTXSID20432728 ;
ECHA InfoCard	100.162.054
Chemical and physical data
Formula	C23H24Cl2N2O3
Molar mass	447.36 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
	SMILES CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4; ; C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl;
	InChI InChI=1S/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3 ; Key:FSFZRNZSZYDVLI-UHFFFAOYSA-N ;
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GW-405,833 (L-768,242) is a drug that acts as a potent and selective partial agonist for the cannabinoid receptor subtype CB₂, with an EC₅₀ of 0.65 nM and selectivity of around 1200x for CB₂ over CB₁ receptors.[1][2] Animal studies have shown it to possess antiinflammatory and anti-hyperalgesic effects at low doses, followed by ataxia and analgesic effects when the dose is increased.[3][4] Selective CB₂ agonist drugs such as GW-405,833 are hoped to be particularly useful in the treatment of allodynia and neuropathic pain for which current treatment options are often inadequate.[5][6]

References

Huffman JW (September 2000). "The search for selective ligands for the CB2 receptor". Current Pharmaceutical Design. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.
Marriott KS, Huffman JW. "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT (April 2002). "CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain". Pain. 96 (3): 253–60. doi:10.1016/s0304-3959(01)00454-7. PMID 11972997.
Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, et al. (April 2005). "Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy". Neuropharmacology. 48 (5): 658–72. doi:10.1016/j.neuropharm.2004.12.008. PMID 15814101.
Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A (March 2006). "CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms". The European Journal of Neuroscience. 23 (6): 1530–8. doi:10.1111/j.1460-9568.2006.04684.x. PMID 16553616.
Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H (June 2009). "Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain". Naunyn-Schmiedeberg's Archives of Pharmacology. 379 (6): 627–36. doi:10.1007/s00210-008-0386-4. PMID 19152053.

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[1] Huffman JW (September 2000). "The search for selective ligands for the CB2 receptor". Current Pharmaceutical Design. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.

[2] Marriott KS, Huffman JW. "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.

[3] Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT (April 2002). "CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain". Pain. 96 (3): 253–60. doi:10.1016/s0304-3959(01)00454-7. PMID 11972997.

[4] Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, et al. (April 2005). "Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy". Neuropharmacology. 48 (5): 658–72. doi:10.1016/j.neuropharm.2004.12.008. PMID 15814101.

[5] Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A (March 2006). "CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms". The European Journal of Neuroscience. 23 (6): 1530–8. doi:10.1111/j.1460-9568.2006.04684.x. PMID 16553616.

[6] Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H (June 2009). "Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain". Naunyn-Schmiedeberg's Archives of Pharmacology. 379 (6): 627–36. doi:10.1007/s00210-008-0386-4. PMID 19152053.