SR-144,528

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SR-144,528
SR-144528 structure.png
Systematic (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
Clinical data
Legal status ?
Identifiers
CAS number 192703-06-3 YesY
ATC code None
PubChem CID 3081355
ChEMBL CHEMBL381689 N
Chemical data
Formula C29H34ClN3O 
Mol. mass 476.051
 N (what is this?)  (verify)

SR144528 is a drug that acts as a potent and highly selective CB2 receptor inverse agonist, with a Ki of 0.6nM at CB2 and 400nM at the related CB1 receptor.[1][2] It is used in scientific research for investigating the function of the CB2 receptor,[3][4][5] 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.[6][7][8] It has also been found to be an inhibitor of acyl-coenzymeA:cholesterol acyltransferase, an effect that appears to be independent from its action on CB2 receptors.[9]

See also[edit]

References[edit]

  1. ^ Rinaldi-Carmona M, et al. (February 1998). "SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor". The Journal of Pharmacology and Experimental Therapeutics 284 (2): 644–50. PMID 9454810. 
  2. ^ Portier M, et al. (February 1999). "SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist". The Journal of Pharmacology and Experimental Therapeutics 288 (2): 582–9. PMID 9918562. 
  3. ^ Gouldson P, et al. (July 2000). "Mutational analysis and molecular modelling of the antagonist SR 144528 binding site on the human cannabinoid CB(2) receptor". European Journal of Pharmacology 401 (1): 17–25. doi:10.1016/S0014-2999(00)00439-8. PMID 10915832. 
  4. ^ Nackley AG, Makriyannis A, Hohmann AG (2003). "Selective activation of cannabinoid CB(2) receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation". Neuroscience 119 (3): 747–57. doi:10.1016/S0306-4522(03)00126-X. PMID 12809695. 
  5. ^ Páldy E, et al. (December 2008). "CB(2) cannabinoid receptor antagonist SR144528 decreases mu-opioid receptor expression and activation in mouse brainstem: role of CB(2) receptor in pain". Neurochemistry International 53 (6-8): 309–16. doi:10.1016/j.neuint.2008.08.005. PMID 18804501. 
  6. ^ Lay L, Angus JA, Wright CE (March 2000). "Pharmacological characterisation of cannabinoid CB(1) receptors in the rat and mouse". European Journal of Pharmacology 391 (1-2): 151–61. doi:10.1016/S0014-2999(00)00062-5. PMID 10720647. 
  7. ^ Germanò MP, et al. (February 2001). "Cannabinoid CB1-mediated inhibition of stress-induced gastric ulcers in rats". Naunyn-Schmiedeberg's Archives of Pharmacology 363 (2): 241–4. doi:10.1007/s002100000360. PMID 11218077. 
  8. ^ Abalo R, et al. (June 2010). "The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55,212-2 on gastrointestinal motility in the rat". Neurogastroenterology and Motility : the Official Journal of the European Gastrointestinal Motility Society 22 (6): 694–e206. doi:10.1111/j.1365-2982.2009.01466.x. PMID 20132133. 
  9. ^ Thewke D, et al. (April 2009). "AM-251 and SR144528 are acyl CoA:cholesterol acyltransferase inhibitors". Biochemical and Biophysical Research Communications 381 (2): 181–6. doi:10.1016/j.bbrc.2009.02.020. PMC 2665256. PMID 19338772.