SR144528   Click here for help

GtoPdb Ligand ID: 751

Synonyms: SR 144528 | SR-144528
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SR144528 is a selective CB2 receptor antagonist with potential anti-inflammatory action.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 46.92
Molecular weight 475.24
XLogP 7.68
No. Lipinski's rules broken 1
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Canonical SMILES Cc1ccc(cc1)Cn1nc(cc1c1ccc(c(c1)C)Cl)C(=O)NC1C2(C)CCC(C1(C)C)C2
Isomeric SMILES Cc1ccc(cc1)Cn1nc(cc1c1ccc(c(c1)C)Cl)C(=O)N[C@H]1[C@@]2(C)CC[C@@H](C1(C)C)C2
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
1. Oka S, Wakui J, Ikeda S, Yanagimoto S, Kishimoto S, Gokoh M, Nasui M, Sugiura T. (2006)
Involvement of the cannabinoid CB2 receptor and its endogenous ligand 2-arachidonoylglycerol in oxazolone-induced contact dermatitis in mice.
J Immunol, 177 (12): 8796-805. [PMID:17142782]
2. Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, Oustric D, Sarran M, Bouaboula M, Calandra B et al.. (1998)
SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor.
J Pharmacol Exp Ther, 284 (2): 644-50. [PMID:9454810]
3. Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG. (1999)
Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630.
Br J Pharmacol, 126: 665-672. [PMID:10188977]