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 ;
ChEBI	CHEBI:146245;
ChEMBL	ChEMBL381791 ;
CompTox Dashboard (EPA)	DTXSID50940947 ;
Chemical and physical data
Formula	C29H34ClN3O
Molar mass	476.06 g·mol−1
3D model (JSmol)	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 0.6 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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[pmid9454810-1] 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.

[pmid9918562-2] 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.

[pmid10915832-3] 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.

[pmid12809695-4] 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.

[pmid18804501-5] 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.

[pmid10720647-7] 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.

[pmid11218077-8] 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.

[pmid20132133-9] 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.

[pmid19338772-10] 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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See also

References