SR-144,528

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408972278

| IUPAC_name = 5-(4-Chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl]-1H-pyrazole-3-carboxamide

| image = SR-144,528.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 751

| CAS_number_Ref = {{cascite|correct|cas}}

| CAS_number = 192703-06-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3081355

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

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

| ChEMBL = 381791

| ChEBI = 146245

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

| ChemSpiderID = 2338975

| chemical_formula =

| C=29 | H=34 | Cl=1 | N=3 | O=1

| smiles = CC1=CC=C(C=C1)CN2C(=CC(=N2)C(=O)N[C@H]3[C@]4(CC[C@H](C4)C3(C)C)C)C5=CC(=C(C=C5)Cl)C

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

| StdInChI = 1S/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1

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

| StdInChIKey = SUGVYNSRNKFXQM-XRHWURSXSA-N

}}

SR144528 is a drug that acts as a potent and highly selective CB₂ receptor inverse agonist, with a K_i of 0.6 nM at CB₂ and 400 nM at the related CB₁ receptor.{{cite journal | vauthors = Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, Oustric D, Sarran M, Bouaboula M, Calandra B, Portier M, Shire D, Brelière JC, Le Fur GL | display-authors = 6 | title = SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 284 | issue = 2 | pages = 644–50 | date = February 1998 | pmid = 9454810 | url = http://jpet.aspetjournals.org/content/284/2/644.long }}{{cite journal | vauthors = Portier M, Rinaldi-Carmona M, Pecceu F, Combes T, Poinot-Chazel C, Calandra B, Barth F, le Fur G, Casellas P | display-authors = 6 | title = SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 288 | issue = 2 | pages = 582–9 | date = February 1999 | pmid = 9918562 | url = http://jpet.aspetjournals.org/content/288/2/582.long }} It is used in scientific research for investigating the function of the CB₂ receptor,{{cite journal | vauthors = Gouldson P, Calandra B, Legoux P, Kernéis A, Rinaldi-Carmona M, Barth F, Le Fur G, Ferrara P, Shire D | display-authors = 6 | title = Mutational analysis and molecular modelling of the antagonist SR 144528 binding site on the human cannabinoid CB(2) receptor | journal = European Journal of Pharmacology | volume = 401 | issue = 1 | pages = 17–25 | date = July 2000 | pmid = 10915832 | doi = 10.1016/S0014-2999(00)00439-8 }}{{cite journal | vauthors = Nackley AG, Makriyannis A, Hohmann AG | title = Selective activation of cannabinoid CB(2) receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation | journal = Neuroscience | volume = 119 | issue = 3 | pages = 747–57 | date = 4 July 2003 | pmid = 12809695 | doi = 10.1016/S0306-4522(03)00126-X | s2cid = 6447695 | authorlink2 = Alexandros Makriyannis }}{{cite journal | vauthors = Páldy E, Bereczki E, Sántha M, Wenger T, Borsodi A, Zimmer A, Benyhe S | title = CB(2) cannabinoid receptor antagonist SR144528 decreases mu-opioid receptor expression and activation in mouse brainstem: role of CB(2) receptor in pain | journal = Neurochemistry International | volume = 53 | issue = 6–8 | pages = 309–16 | date = December 2008 | pmid = 18804501 | doi = 10.1016/j.neuint.2008.08.005 | s2cid = 22671432 }}{{Cite journal| vauthors = Saroz Y, Kho DT, Glass M, Graham ES, Grimsey NL |date=2019-10-19|title=Cannabinoid Receptor 2 (CB 2 ) Signals via G-alpha-s and Induces IL-6 and IL-10 Cytokine Secretion in Human Primary Leukocytes|journal=ACS Pharmacology & Translational Science|volume=2|issue=6|language=en|pages=414–428|doi=10.1021/acsptsci.9b00049|pmid=32259074|pmc=7088898|issn=2575-9108|doi-access=free}} as well as for studying the effects of CB₁ receptors in isolation, as few CB₁ agonists that do not also show significant activity as CB₂ agonists are available.{{cite journal | vauthors = Lay L, Angus JA, Wright CE | title = Pharmacological characterisation of cannabinoid CB(1) receptors in the rat and mouse | journal = European Journal of Pharmacology | volume = 391 | issue = 1–2 | pages = 151–61 | date = March 2000 | pmid = 10720647 | doi = 10.1016/S0014-2999(00)00062-5 }}{{cite journal | vauthors = Germanò MP, D'Angelo V, Mondello MR, Pergolizzi S, Capasso F, Capasso R, Izzo AA, Mascolo N, De Pasquale R | display-authors = 6 | title = Cannabinoid CB1-mediated inhibition of stress-induced gastric ulcers in rats | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 363 | issue = 2 | pages = 241–4 | date = February 2001 | pmid = 11218077 | doi = 10.1007/s002100000360 | s2cid = 2655432 }}{{cite journal | vauthors = Abalo R, Cabezos PA, Vera G, Fernández-Pujol R, Martín MI | title = The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55,212-2 on gastrointestinal motility in the rat | journal = Neurogastroenterology and Motility | volume = 22 | issue = 6 | pages = 694–e206 | date = June 2010 | pmid = 20132133 | doi = 10.1111/j.1365-2982.2009.01466.x | s2cid = 10520671 }} It has also been found to be an inhibitor of sterol O-acyltransferase, an effect that appears to be independent from its action on CB₂ receptors.{{cite journal | vauthors = Thewke D, Freeman-Anderson N, Pickle T, Netherland C, Chilton C | title = AM-251 and SR144528 are acyl CoA:cholesterol acyltransferase inhibitors | journal = Biochemical and Biophysical Research Communications | volume = 381 | issue = 2 | pages = 181–6 | date = April 2009 | pmid = 19338772 | pmc = 2665256 | doi = 10.1016/j.bbrc.2009.02.020 }}