SR-144,528: Difference between revisions

| IUPAC_name = N-[(1S)-endo-1,3,3-trimethylbicyclo [2.2.1]heptan2-yl]-5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-1H-pyrazole-3-carboxamide

| image = SR-144528_structure.png

| CAS_number = 192703-06-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3081355

| DrugBank =

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

| molecular_weight = 476.051

| smiles = Cc5ccc(cc5)Cn3nc(cc3-c(cc2C)ccc2Cl)C(=O)NC1C(C)(C)C(C4)CCC14C

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category=

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration =

'''SR-144,528''' is a drug which acts as a potent and highly selective [[cannabinoid receptor 2|CB₂]] [[Receptor (biochemistry)|receptor]] [[inverse agonist]], with a [[Dissociation constant#Protein-ligand binding|K_i]] of 0.6nM at CB₂ and 400nM at the related CB₁ receptor.<ref name="pmid9454810">{{cite journal |author=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 |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 |year=1998 |month=February |pmid=9454810 |doi= |url=}}</ref><ref name="pmid9918562">{{cite journal |author=Portier M, Rinaldi-Carmona M, Pecceu F, Combes T, Poinot-Chazel C, Calandra B, Barth F, le Fur G, Casellas P |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 |year=1999 |month=February |pmid=9918562 |doi= |url=}}</ref> It is used in scientific research for investigating the function of the CB₂ receptor,<ref name="pmid10915832">{{cite journal |author=Gouldson P, Calandra B, Legoux P, Kernéis A, Rinaldi-Carmona M, Barth F, Le Fur G, Ferrara P, Shire D |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 |year=2000 |month=July |pmid=10915832 |doi= |url=}}</ref><ref name="pmid12809695">{{cite journal |author=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 |year=2003 |pmid=12809695 |doi= |url=}}</ref><ref name="pmid18804501">{{cite journal |author=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 |year=2008 |month=December |pmid=18804501 |doi=10.1016/j.neuint.2008.08.005 |url=}}</ref> as well as for studying the effects of CB₁ receptors in isolation, as few CB₁ agonists are available which do not also show significant activity as CB₂ agonists.<ref name="pmid10720647">{{cite journal |author=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 |year=2000 |month=March |pmid=10720647 |doi= |url=}}</ref><ref name="pmid11218077">{{cite journal |author=Germanò MP, D'Angelo V, Mondello MR, Pergolizzi S, Capasso F, Capasso R, Izzo AA, Mascolo N, De Pasquale R |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 |year=2001 |month=February |pmid=11218077 |doi= |url=}}</ref><ref name="pmid20132133">{{cite journal |author=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 : the Official Journal of the European Gastrointestinal Motility Society |volume=22 |issue=6 |pages=694–e206 |year=2010 |month=June |pmid=20132133 |doi=10.1111/j.1365-2982.2009.01466.x |url=}}</ref> It has also been found to be an inhibitor of [[Sterol O-acyltransferase|acyl-coenzymeA:cholesterol acyltransferase]], an effect that appears to be independent from its action on CB₂ receptors.<ref name="pmid19338772">{{cite journal |author=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 |year=2009 |month=April |pmid=19338772 |pmc=2665256 |doi=10.1016/j.bbrc.2009.02.020 |url=}}</ref>

==References==

[[Category:Amides]]

[[Category:Organochlorides]]