SR-144,528

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SR-144,528
SR-144,528.svg
Systematic (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
Identifiers
CAS Number 192703-06-3 YesY
ATC code none
PubChem CID 3081355
IUPHAR/BPS 751
ChemSpider 2338975 N
ChEMBL CHEMBL381791 N
Chemical data
Formula C29H34ClN3O
Molar mass 476.053 g/mol
 NYesY (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 sterol O-acyltransferase, an effect that appears to be independent from its action on CB2 receptors.[9]

See also[edit]

References[edit]

  1. ^ Rinaldi-Carmona, Murielle; Barth, Francis; Millan, José; Derocq, Jean-Marie; Casellas, Pierre; Congy, Christian; Oustric, Didier; Sarran, Martine; Bouaboula, Monsif; Calandra, Bernard; Portier, Marielle; Shire, David; Brelière, Jean-Claude; Fur, Gérard Le (1 February 1998). "SR 144528, the First Potent and Selective Antagonist of the CB2 Cannabinoid Receptor". Journal of Pharmacology and Experimental Therapeutics. 284 (2): 644–650. ISSN 1521-0103. PMID 9454810. 
  2. ^ Portier, Marielle; Rinaldi-Carmona, Murielle; Pecceu, Florence; Combes, Thérèse; Poinot-Chazel, Caroline; Calandra, Bernard; Barth, Francis; Fur, Gérard Le; Casellas, Pierre (1 February 1999). "SR 144528, an Antagonist for the Peripheral Cannabinoid Receptor that Behaves as an Inverse Agonist". Journal of Pharmacology and Experimental Therapeutics. 288 (2): 582–589. ISSN 1521-0103. PMID 9918562. 
  3. ^ Gouldson, Paul; Calandra, Bernard; Legoux, Pascale; Kernéis, Aimée; Rinaldi-Carmona, Murielle; Barth, Francis; Le Fur, Gérard; Ferrara, Pascual; Shire, David (28 July 2000). "Mutational analysis and molecular modelling of the antagonist SR 144528 binding site on the human cannabinoid CB2 receptor". European Journal of Pharmacology. 401 (1): 17–25. doi:10.1016/S0014-2999(00)00439-8. PMID 10915832. 
  4. ^ Nackley, A. G; Makriyannis, A; Hohmann, A. G (4 July 2003). "Selective activation of cannabinoid CB2 receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation". Neuroscience. 119 (3): 747–757. doi:10.1016/S0306-4522(03)00126-X. PMID 12809695. 
  5. ^ Páldy, Eszter; Bereczki, Erika; Sántha, Miklós; Wenger, Tibor; Borsodi, Anna; Zimmer, Andreas; Benyhe, Sándor (1 December 2008). "CB2 cannabinoid receptor antagonist SR144528 decreases μ-opioid receptor expression and activation in mouse brainstem: Role of CB2 receptor in pain". Neurochemistry International. 53 (6–8): 309–316. doi:10.1016/j.neuint.2008.08.005. PMID 18804501. 
  6. ^ Lay, Lucy; Angus, James A; Wright, Christine E (10 March 2000). "Pharmacological characterisation of cannabinoid CB1 receptors in the rat and mouse". European Journal of Pharmacology. 391 (1–2): 151–161. doi:10.1016/S0014-2999(00)00062-5. PMID 10720647. 
  7. ^ Germanò, Maria Paola; D'Angelo, Valeria; Mondello, Maria Rita; Pergolizzi, Simona; Capasso, Francesco; Capasso, Raffaele; Izzo, Angelo A.; Mascolo, Nicola; Pasquale, Rita De (1 February 2001). "Cannabinoid CB1-mediated inhibition of stress-induced gastric ulcers in rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 363 (2): 241–244. doi:10.1007/s002100000360. ISSN 1432-1912. PMID 11218077. 
  8. ^ Abalo, R.; Cabezos, P. A.; Vera, G.; Fernández-pujol, R.; Martín, M. I. (1 June 2010). "The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55,212-2 on gastrointestinal motility in the rat". Neurogastroenterology & Motility. 22 (6): 694–e206. doi:10.1111/j.1365-2982.2009.01466.x. ISSN 1365-2982. PMID 20132133. 
  9. ^ Thewke, Douglas; Freeman-Anderson, Natalie; Pickle, Theresa; Netherland, Courtney; Chilton, Courtney (3 April 2009). "AM-251 and SR144528 are acyl CoA:cholesterol acyltransferase inhibitors". Biochemical and Biophysical Research Communications. 381 (2): 181–186. doi:10.1016/j.bbrc.2009.02.020. PMC 2665256free to read. PMID 19338772.