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GW-405,833

Summary

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]

GW-405,833
Identifiers
  • 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
CAS Number
  • 180002-83-9 checkY
PubChem CID
  • 9911463
ChemSpider
  • 8087114 ☒N
UNII
  • 85K154W99L
ChEMBL
  • ChEMBL73711 ☒N
CompTox Dashboard (EPA)
  • DTXSID20432728 Edit this at Wikidata
ECHA InfoCard100.162.054 Edit this at Wikidata
Chemical and physical data
FormulaC23H24Cl2N2O3
Molar mass447.36 g·mol−1
3D model (JSmol)
  • Interactive image
  • Interactive image
  • 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=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 ☒N
  • Key:FSFZRNZSZYDVLI-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

References edit

  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 (2008). "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. S2CID 24816928.
  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. S2CID 10121434.
  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. S2CID 19266396.
  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. S2CID 25085194.