rimonabant   Click here for help

GtoPdb Ligand ID: 743

Synonyms: A 281 | Acomplia® | SR 141716
Approved drug PDB Ligand
rimonabant is an approved drug (EMA (2007))
Compound class: Synthetic organic
Comment: EMA-only approval in 2007 withdrawn on 16 January 2009
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.64
Molecular weight 462.08
XLogP 6.13
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
Isomeric SMILES Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
InChI InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
InChI Key JZCPYUJPEARBJL-UHFFFAOYSA-N
References
1. Brown AJ, Daniels DA, Kassim M, Brown S, Haslam CP, Terrell VR, Brown J, Nichols PL, Staton PC, Wise A et al.. (2011)
Pharmacology of GPR55 in yeast and identification of GSK494581A as a mixed-activity glycine transporter subtype 1 inhibitor and GPR55 agonist.
J. Pharmacol. Exp. Ther., 337 (1): 236-46. [PMID:21233197]
2. Felder CC, Joyce KE, Briley EM, Glass M, Mackie KP, Fahey KJ, Cullinan GJ, Hunden DC, Johnson DW, Chaney MO et al.. (1998)
LY320135, a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation.
J. Pharmacol. Exp. Ther., 284 (1): 291-7. [PMID:9435190]
3. Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, Lai Y, Ma AL, Mitchell RL. (1995)
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
Mol. Pharmacol., 48 (3): 443-50. [PMID:7565624]
4. Henstridge CM, Balenga NA, Schröder R, Kargl JK, Platzer W, Martini L, Arthur S, Penman J, Whistler JL, Kostenis E, Waldhoer M, Irving AJ. (2010)
GPR55 ligands promote receptor coupling to multiple signalling pathways.
Br. J. Pharmacol., 160 (3): 604-14. [PMID:20136841]
5. Rinaldi-Carmona M, Barth F, Héaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Néliat G, Caput D et al.. (1994)
SR141716A, a potent and selective antagonist of the brain cannabinoid receptor.
FEBS Lett., 350 (2-3): 240-4. [PMID:8070571]
6. Ruiu S, Pinna GA, Marchese G, Mussinu JM, Saba P, Tambaro S, Casti P, Vargiu R, Pani L. (2003)
Synthesis and characterization of NESS 0327: a novel putative antagonist of the CB1 cannabinoid receptor.
J. Pharmacol. Exp. Ther., 306 (1): 363-70. [PMID:12663689]
7. Showalter VM, Compton DR, Martin BR, Abood ME. (1996)
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
J. Pharmacol. Exp. Ther., 278 (3): 989-99. [PMID:8819477]