SR-144,528

SR-144,528

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
Identifiers
CAS Number	192703-06-3
ATC code	None
PubChem	CID 3081355
IUPHAR/BPS	751
ChEMBL	CHEMBL381689
Chemical data
Formula	C29H34ClN3O
Molar mass	476.051 g/mol
SMILES Cc5ccc(cc5)Cn3nc(cc3-c(cc2C)ccc2Cl)C(=O)NC1C(C)(C)C(C4)CCC14C
(what is this?)  (verify)

SR144528 is a drug that acts as a potent and highly selective CB₂ receptor inverse agonist, with a K_i 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

• NESS-040C5
• SR141716
• N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide

References

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.