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GW-405,833

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Chemical compound
Pharmaceutical compound
GW-405,833
Identifiers
  • 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.162.054Edit this at Wikidata
Chemical and physical data
FormulaC23H24Cl2N2O3
Molar mass447.36 g·mol−1
3D model (JSmol)
  • 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)

GW-405,833 (L-768,242) is a drug that acts as a potent and selectivepartial agonist for thecannabinoid receptor subtypeCB2, with anEC50 of 0.65 nM and selectivity of around 1200x for CB2 overCB1 receptors.[1][2] Animal studies have shown it to possessantiinflammatory and anti-hyperalgesic effects at low doses, followed byataxia andanalgesic 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 ofallodynia andneuropathic pain for which current treatment options are often inadequate.[5][6]

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.
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