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SR-144,528
Clinical data
ATC code
  • none
Identifiers
  • 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
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEBI
ChEMBL
CompTox Dashboard ( EPA)
Chemical and physical data
FormulaC29H34ClN3O
Molar mass476.06 g·mol−1
3D model ( JSmol)
  • 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
  • InChI=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 ☒N
  • Key:SUGVYNSRNKFXQM-XRHWURSXSA-N ☒N
 ☒NcheckY  (what is this?)   (verify)

SR144528 is a drug that acts as a potent and highly selective CB2 receptor inverse agonist, with a Ki of 0.6 nM at CB2 and 400 nM at the related CB1 receptor. [1] [2] It is used in scientific research for investigating the function of the CB2 receptor, [3] [4] [5] [6] 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. [7] [8] [9] 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. [10]

See also

References

  1. ^ Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, 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, Rinaldi-Carmona M, Pecceu F, Combes T, Poinot-Chazel C, Calandra B, 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, Calandra B, Legoux P, Kernéis A, Rinaldi-Carmona M, Barth F, 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 (4 July 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. S2CID  6447695.
  5. ^ Páldy E, Bereczki E, Sántha M, Wenger T, Borsodi A, Zimmer A, Benyhe S (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. S2CID  22671432.
  6. ^ Saroz Y, Kho DT, Glass M, Graham ES, Grimsey NL (2019-10-19). "Cannabinoid Receptor 2 (CB 2 ) Signals via G-alpha-s and Induces IL-6 and IL-10 Cytokine Secretion in Human Primary Leukocytes". ACS Pharmacology & Translational Science. 2 (6): 414–428. doi: 10.1021/acsptsci.9b00049. ISSN  2575-9108. PMC  7088898. PMID  32259074.
  7. ^ 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.
  8. ^ Germanò MP, D'Angelo V, Mondello MR, Pergolizzi S, Capasso F, Capasso R, 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. S2CID  2655432.
  9. ^ Abalo R, Cabezos PA, Vera G, Fernández-Pujol R, Martín MI (June 2010). "The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55,212-2 on gastrointestinal motility in the rat". Neurogastroenterology and Motility. 22 (6): 694–e206. doi: 10.1111/j.1365-2982.2009.01466.x. PMID  20132133. S2CID  10520671.
  10. ^ Thewke D, Freeman-Anderson N, Pickle T, Netherland C, Chilton C (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.
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