GW-405,833

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424782539

| IUPAC_name = 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole

| image = GW-405,833-2D-skeletal.svg

| image_class = skin-invert-image

| width = 240px

| tradename =

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| index_label =

| index2_label =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 180002-83-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 85K154W99L

| PubChem = 9911463

| ChEBI = 92184

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 73711

| ChemSpiderID = 8087114

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| smiles = CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4

| smiles2 = C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = FSFZRNZSZYDVLI-UHFFFAOYSA-N

| C=23 | H=24 | Cl=2 | N=2 | O=3

}}

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.{{cite journal | vauthors = Huffman JW | title = The search for selective ligands for the CB2 receptor | journal = Current Pharmaceutical Design | volume = 6 | issue = 13 | pages = 1323–37 | date = September 2000 | pmid = 10903395 | doi = 10.2174/1381612003399347 }}{{cite journal | vauthors = Marriott KS, Huffman JW | title = Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor | journal = Current Topics in Medicinal Chemistry | year = 2008 | volume = 8 | issue = 3 | pages = 187–204 | pmid = 18289088 | doi = 10.2174/156802608783498014 }} 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.{{cite journal | vauthors = Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT | title = CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain | journal = Pain | volume = 96 | issue = 3 | pages = 253–60 | date = April 2002 | pmid = 11972997 | doi = 10.1016/s0304-3959(01)00454-7 | s2cid = 24816928 }}{{cite journal | vauthors = Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, Mark L, Pearson MS, Miller W, Shan S, Rabadi L, Rotshteyn Y, Chaffer SM, Turchin PI, Elsemore DA, Toth M, Koetzner L, Whiteside GT | display-authors = 6 | title = Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy | journal = Neuropharmacology | volume = 48 | issue = 5 | pages = 658–72 | date = April 2005 | pmid = 15814101 | doi = 10.1016/j.neuropharm.2004.12.008 | s2cid = 10121434 }} 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.{{cite journal | vauthors = Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A | title = CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms | journal = The European Journal of Neuroscience | volume = 23 | issue = 6 | pages = 1530–8 | date = March 2006 | pmid = 16553616 | doi = 10.1111/j.1460-9568.2006.04684.x | s2cid = 19266396 }}{{cite journal | vauthors = Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H | title = Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 379 | issue = 6 | pages = 627–36 | date = June 2009 | pmid = 19152053 | doi = 10.1007/s00210-008-0386-4 | s2cid = 25085194 }}