SR-144,528

SR-144,528

Clinical data
ATC code	none
Identifiers
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
CAS Number	192703-06-3
PubChem (CID)	3081355
IUPHAR/BPS	751
ChemSpider	2338975
ChEMBL	CHEMBL381791
Chemical and physical data
Formula	C29H34ClN3O
Molar mass	476.053 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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 Key:SUGVYNSRNKFXQM-XRHWURSXSA-N
(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 sterol O-acyltransferase, an effect that appears to be independent from its action on CB₂ receptors.^[9]

See also

• NESS-040C5
• Rimonabant
• MN-25

References

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 2665256. PMID 19338772.