Home GPCR & G Protein Cannabinoid Receptor antagonist Rimonabant (SR141716)

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Rimonabant (SR141716) Cannabinoid Receptor antagonist

Cat.No.S3021

Rimonabant (SR141716) is a selective antagonist of CB1 with IC50 of 13.6 nM and EC50 of 17.3 nM in hCB1 transfected HEK 293 membrane, and it is also a dual inhibitor of acyl CoA:cholesterol acyltransferases(ACAT) 1 and 2 that inhibits mycobacterial MmpL3.
Rimonabant (SR141716) Cannabinoid Receptor antagonist Chemical Structure

Chemical Structure

Molecular Weight: 463.79

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Quality Control

Batch: Purity: 99.67%
99.67

Cell Culture, Treatment & Working Concentration

Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
CHO cells Function assay Ability to displace [3H]-SR- 141716A binding to human CB1 receptor expressed in CHO cell membranes, Ki=8.9 nM 10465552
CHO Function assay Antagonistic activity towards cannabinoid receptor 1 expressed as [3H]Arachidonic acid release in CHO cells, Kd=0.002512μM 14736243
CHO Function assay Displacement of CP-55940 binding from recombinant human cannabinoid receptor 1 expressed in CHO cells, Ki=0.025μM 14736243
CHO Function assay Affinity to displace CP-55940 binding from Cannabinoid receptor 2 of human expressed in CHO cells, Ki=1.58μM 14736243
CHO Function assay Inhibitory concentration against human recombinant cannabinoid receptor type 1 expressed in Chinese Hamster Ovary (CHO) cells, IC50=0.006μM 15713403
CHO Function assay In vitro cannabinoid receptor 1 antagonism of [3H]arachidonic acid release by CHO cells, Kd=0.002512μM 15771428
CHO Function assay In vitro displacement of CP-55940 binding to human CB1 receptor expressed in CHO cells, Ki=0.025μM 15771428
CHO Function assay In vitro displacement of CP-55940 binding to human CB2 receptor expressed in CHO cells, Ki=1.58μM 15771428
CHO Function assay Inhibition of [3H]SR-141,716A binding to human CB1 receptor expressed in CHO cells, Ki=0.0054μM 15801840
CHO Function assay Antagonistic activity against cannabinoid receptor 1 measured by CP-55940 induced arachnoid acid release in CHO cells, Kd=0.002512μM 16140010
CHO Function assay Displacement of specific CP-55940 binding in CHO cells stably transfected with human cannabinoid receptor 1, Ki=0.025μM 16140010
CHO Function assay Displacement of specific CP-55940 binding in CHO cells stably transfected with human cannabinoid receptor 2, Ki=1.58μM 16140010
CHOK1 Function assay Functional activity at human CB1 receptor transfected in CHOK1 cells by [35SGTP]gammaS assay, Ki=0.001μM 16263283
HEK293 Function assay Displacement of [3H]SR-141716 from human CB1 receptor transfected in HEK293 cells, Ki=0.0021μM 16263283
CHO Function assay Displacement of [3H]SR141716A from human CB1 receptor expressed in CHO cells, Ki=0.0054μM 16279809
HEK293 Function assay Displacement of [3H]SR-141716 from human CB1 receptor expressed in HEK293 cells, Kd=0.0018μM 17004712
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, Ki=0.0071μM 17004712
HEK293 Function assay Displacement of [3H]WIN-55212-2 from human CB1 receptor expressed in HEK293 cells, Ki=0.018μM 17004712
CHO Function assay Inhibition of [3H]CP-55940 binding to human recombinant CB1 receptor in CHO cells, IC50=0.0061μM 17181138
CHO Function assay Inhibition of [3H]CP-55940 binding to human recombinant CB2 receptor in CHO cells, IC50=0.6μM 17181138
CHO Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in CHO cells, IC50=0.0061μM 17293109
CHO Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in CHO cells, IC50=0.6033μM 17293109
HEK293 Function assay Displacement of [3H]CP-559440 from human CB1 receptor expressed in HEK293 cells, Ki=0.0011μM 17383180
HEK293 Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells, Ki=0.016μM 17942307
HEK293 Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells, Ki=1.64μM 17942307
HEK293 Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells, Ki=0.047μM 17979261
CHOK1 Function assay Displacement of [3H]WIN-552122 from human recombinant CB2 receptor expressed in CHOK1 cells, Ki=1.99μM 17979261
HEK293 Function assay Displacement of radioligand from human CB1 receptor expressed in HEK293 cells, Ki=0.0018μM 18083560
HEK293 EBNA Function assay Inverse agonist activity at human CB1 receptor expressed in HEK293 EBNA cells by [35S]GTPgammaS incorporation assay, EC50=0.004μM 18083560
HEK293 Function assay Displacement of radioligand from human CB2 receptor expressed in HEK293 cells, Ki=0.554μM 18083560
CHOK1 Function assay Antagonist activity at human CB1 receptor expressed in CHOK1 cells by luciferase assay, IC50=0.12μM 18243711
CHOK1 Function assay Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHOK1 cells, IC50=1.76μM 18243711
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK cells, Ki=0.012μM 18293908
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK cells, Ki=0.79μM 18293908
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells, Ki=0.006μM 18335976
CHO Function assay Displacement of [3H]WIN-55212-2 from human cannabinoid CB2 receptor expressed in CHO cells, IC50=1.76μM 18337096
CHO Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells, Ki=0.025μM 18342403
CHO Function assay Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHO cells, Ki=1.58μM 18342403
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, Ki=0.0024μM 18363352
CHO Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells, Ki=0.56μM 18363352
SF9 Function assay Antagonist activity at rat CB1 receptor in SF9 cells assessed as inhibition of CP-55940-stimulated GTPgammaS binding, Ki=0.00031μM 18448340
SF9 Function assay Antagonist activity at human CB1 receptor expressed in SF9 cells assessed as inhibition of CP-55940-stimulated GTPgammaS binding, Ki=0.00043μM 18448340
SF9 Function assay Inverse agonist at human CB1 receptor expressed in SF9 cells assessed as decrease in GTPgammaS level, IC50=0.00135μM 18448340
SF9 Function assay Antagonist activity at human CB2 receptor in SF9 cells assessed as inhibition of CP-55940-stimulated GTPgammaS binding, Ki=0.815μM 18448340
HEK293 Function assay Displacement of [3H]CP-55940 form human recombinant CB1 receptor expressed in HEK293 cells by liquid scintillation counting, Ki=0.04μM 18511157
CHO-K1 Function assay Displacement of [3H]SR141716 from human CB1 receptor expressed in CHO-K1 cells, Ki=0.00118μM 18512901
HEK293 Function assay Antagonist activity at human CB1 receptor expressed in HEK293 cells assessed as inhibition of CP-55940-stimulated [35S]GTPgammaS binding, Kd=0.00257μM 18512901
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, Ki=0.00618μM 18512901
CHO-K1 Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO-K1 cells, Ki=0.313μM 18512901
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK cells, Ki=0.008μM 18579386
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK cells, Ki=0.79μM 18579386
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, Ki=0.012μM 18680276
HEK293 Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK293 cells, Ki=0.79μM 18680276
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, IC50=0.015μM 18712856
HEK293 Function assay Antagonist activity at human CB1 receptor expressed in HEK293 cells assessed as inhibition of Eu-GTP binding, EC50=0.0182μM 18712856
HEK293 Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK293 cells, IC50=1.9398μM 18712856
HEK293 Function assay Inverse agonist activity at human CB1 receptor expressed in HEK293 cells assessed as decrease in [35S]gammaGTP binding relative to control 18712856
CHO Function assay Antagonist activity at human CB1 receptor in CHO cells assessed as GTPgammaS binding, Kb=0.000698μM 18800770
CHOK1 Function assay Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHOK1 cells by liquid scintillation spectrometry, IC50=1.76μM 18954042
CHO Function assay Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHO cells, IC50=1.76μM 19022666
HEK293 Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK293 cells, IC50=0.0019μM 19095444
HEK293 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells, IC50=0.015μM 19095444
HEK293 Function assay Antagonist activity at human CB1 receptor expressed in HEK293 cells assessed as inhibition of Eu-GTP binding, EC50=0.0182μM 19095444
CHO-K1 Function assay Antagonist activity against human CB1 receptor expressed in CHO-K1 cells by [35S]GTPgamma binding assay, Ki=0.00019μM 19102698
HEK293 Function assay Displacement of [3H]SR141716A from human CB1 receptor expressed in HEK293 cells, Ki=0.0009μM 19102698
CHOK1 Function assay Displacement of [3H]WIN-55212-2 from human recombinant cannabinoid CB2 receptor expressed in CHOK1 cells by liquid scintillation spectrometry, IC50=1.76μM 19269817
CHOK1 Function assay Antagonist activity at human cannabinoid CB1 receptor expressed in CHOK1 cells assessed as cAMP activity, EC50=0.24μM 19328683
CHOK1 Function assay Antagonist activity at human cannabinoid CB2 receptor expressed in CHOK1 cells assessed as cAMP activity, EC50=31.21μM 19328683
HEK293 Function assay Displacement of [3H]SR141716 from human recombinant CB1 receptor expressed in HEK293 cells, Ki=0.001995μM 19338356
HEK293 Function assay Displacement of [3H]SR141716 from human recombinant CB2 receptor expressed in HEK293 cells, Ki=0.39811μM 19338356
CHOK1 Function assay 10 mins Antagonist activity at human CB1 receptor expressed in CHOK1 cells assessed as inhibition of CP-55940-induced response after 10 mins by GTPgamma[35S] binding assay, Ki=0.0016μM 19351113
HEK293 Function assay Displacement of [3H]rimonabant from human CB1 receptor expressed in HEK293 cells by liquid scintillation counting, Ki=0.0019μM 19520572
HEK293 Function assay Displacement of [3H]CP-55940 from human recombinant CB1R expressed in HEK293 cells, IC50=0.0132μM 19530697
HEK293 Function assay Inverse agonist activity at human recombinant CB1R expressed in HEK293 cells assessed as inhibition of CP-55940-stimulated Eu-GTP binding, EC50=0.0157μM 19530697
HEK293 Function assay Displacement of [3H]CP-55940 from human recombinant CB2R expressed in HEK293 cells, IC50=1.6311μM 19530697
HEK293 Function assay 10 uM Intrinsic activity at human recombinant CB1R expressed in HEK293 cells assessed as Eu-GTP binding at 10 uM relative to basal level 19530697
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK cells, Ki=0.012μM 19595596
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK cells, Ki=0.79μM 19595596
CHO-K1 Function assay Antagonist activity at human CB1 receptor transfected in CHO-K1cells by GTPgamma[35S] binding assay, Ki=0.0016μM 19683918
CHO Function assay Binding affinity to human CB2 receptor expressed in CHO cells by luciferase reporter gene assay, IC50=0.0925μM 19850473
CHOK1 Function assay Displacement of [3H]WIN-552122 from human CB2 receptor expressed in CHOK1 cells, IC50=1.76μM 19850473
CHO-K1 Function assay Antagonist activity at human recombinant CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP-55940-stimulated GTPgammaS binding, IC50=0.0045μM 19954978
CHO-K1 Function assay Inverse agonist activity at human CB1 receptor expressed in CHO-K1 cells by GTPgammaS binding assay, IC50=0.0029μM 20015647
CHO-K1 Function assay Antagonist activity at human CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP-55940-induced GTPgammaS binding, IC50=0.0045μM 20015647
COS7 Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in COS7 cells, IC50=0.0051μM 20015647
CHO Function assay Inverse agonist activity at human recombinant CB1 receptor expressed in CHO cells by luciferase reporter gene assay, IC50=0.108μM 20045337
CHO Function assay 60 mins Inverse agonist activity at human cannabinoid CB1 receptor expressed in CHO cells assessed as inhibition of forskolin-stimulated cAMP accumulation after 60 mins, EC50=0.00011μM 20047779
CHO Function assay 3 hrs Displacement of [3H]CP-55940 from human recombinant cannabinoid CB1 receptor expressed in CHO cells after 3 hrs by liquid scintillation counting, Ki=0.00074μM 20047779
CHO Function assay 10 mins Antagonist activity at human cannabinoid CB1 receptor expressed in CHO cells coexpressing Galpha15/16 assessed as inhibition of CP-55940-induced Ca2+ release after 10 mins by micro plate reader, IC50=0.0032μM 20047779
CHO Function assay 3 hrs Displacement of [3H]CP-55940 from human recombinant cannabinoid CB2 receptor expressed in CHO cells after 3 hrs by liquid scintillation counting, Ki=0.126μM 20047779
CHO Function assay Antagonist activity at human CB1 receptor expressed in CHO cells assessed as inhibition of CP-55940-induced [3H]arachidonic acid release, Kd=0.002512μM 20363132
CHO Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells, Ki=0.025μM 20363132
CHO Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells, Ki=1.58μM 20363132
CHO-K1 Function assay 1 hr Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHO-K1 cells after 1 hr by liquid scintillation counting, IC50=1.76μM 20673729
HEK Function assay Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK cells, Ki=0.012μM 20718492
HEK Function assay Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK cells, Ki=0.79μM 20718492
CHO Function assay Agonist activity at human CB1 receptor expressed in CHO cells co-expressing Galpha16 protein assessed as mobilization of intracellular calcium, Ke=0.0011μM 20845959
HEK293 Function assay Displacement of [3H]SR141716 from human CB1 receptor expressed in HEK293 cells, Ki=0.00118μM 20845959
HEK293 Function assay Displacement of [3H]CP55940 from human CB1 receptor expressed in HEK293 cells, Ki=0.00618μM 20845959
CHOK1 Function assay Displacement of [3H]CP55940 from human CB2 receptor expressed in CHOK1 cells, Ki=0.313μM 20845959
HEK Function assay Displacement of [3H]CP-55,940 from recombinant human CB1 receptor transfected in HEK cells, Ki=0.012μM 20943290
HEK Function assay Displacement of [3H]CP-55,940 from recombinant human CB2 receptor transfected in HEK cells, Ki=0.79μM 20943290
CHO Function assay Displacement of [3H]SR141716A from human CB1 receptor expressed in CHO cells, Ki=0.0009333μM 21334892
Sf9 Function assay Displacement of [3H]CP55940 from human recombinant CB2 receptor expressed in Sf9 cells, Ki=0.85114μM 21334892
CHO Function assay Antagonist activity at CB1 receptor transfected in CHO cells expressing apoaequorin as a reporter for G-protein-coupled receptor-mediated calcium signaling by bioluminescence assay, IC50=0.004μM 21376588
HEK293 Function assay Noncompetitive inhibition of MRP1-mediated E2-17betaG transport in human MRP1 expressing HEK293 cells by Dixon plot, Ki=1.4μM 21511945
HEK293 Function assay Noncompetitive inhibition of MRP4-mediated E2-17betaG transport in human MRP4 expressing HEK293 cells by Dixon plot, Ki=4μM 21511945
HEK293 Function assay Induction of MRP2-mediated E2-17betaG transport in human MRP2 expressing HEK293 cells in presence of 2 uM E2-17betaG 21511945
HEK293 Function assay Inhibition of MRP3-mediated E2-17betaG transport in human MRP3 expressing HEK293 cells in presence of 15 uM E2-17betaG 21511945
HEK293 Function assay Inhibition of MRP1-mediated E2-17betaG transport in human MRP1 expressing HEK293 cells in presence of 0.6 to 5 uM E2-17betaG 21511945
HEK293 Function assay Inhibition of MRP4-mediated E2-17betaG transport in human MRP4 expressing HEK293 cells in presence of 0.6 to 5 uM E2-17betaG 21511945
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK cells, Ki=0.012μM 21702498
HEK Function assay Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK cells, Ki=0.79μM 21702498
CHO Function assay 1 hr Displacement of [3H]CP55940 from human cannabinoid CB2 receptor expressed in CHO cells at pH 7.4 after 1 hr by liquid scintillation counting, IC50=1.98μM 21741835
HEK293 Function assay 5 mins Inhibition of human ERG expressed in HEK293 cells assessed as inhibition of potassium channel current after 5 mins by patch clamp assay, IC50=2.79μM 21741835
CHO Function assay 90 mins Displacement of [3H]BMS-725519 from human CB1 receptor expressed in CHO cells after 90 mins by scintillation counting, Ki=0.00073μM 21962575
CHO-K1 Function assay Antagonist activity at human CB1 receptor expressed in CHO-K1 cells co-expressing Galphaq16 assessed as inhibition of CP55940-induced intracellular calcium mobilization by fluorometry, Ke=0.0011μM 22372835
CHO-K1 Function assay Displacement of [3H]CP55940 from human CB1 receptor expressed in CHO-K1 cells, Ki=0.0062μM 22372835
CHO-K1 Function assay Displacement of [3H]CP55940 from CB2 receptor expressed in CHO-K1 cells, Ki=0.313μM 22372835
HEK Function assay Displacement of [3H]CP-55,940 from human recombinant CB1 receptor transfected in HEK cells, Ki=0.012μM 22548457
HEK Function assay Displacement of [3H]CP-55,940 from human recombinant CB2 receptor transfected in HEK cells, Ki=0.79μM 22548457
CHO Function assay 2 hrs Displacement of [3H]CP55,940 from human CB1 receptor expressed in CHO cells after 2 hrs by liquid scintillation counter, Ki=0.0126μM 22916707
CHO Function assay 2 hrs Displacement of [3H]CP55,940 from human CB2 receptor expressed in CHO cells after 2 hrs by liquid scintillation counter, Ki=0.9μM 22916707
CHO Function assay Inverse agonist activity against CB1 receptor expressed in human CHO cells assessed as effect on forskolin-stimulated cAMP level, IC50=0.051μM 22959249
CHO Function assay 1 hr Displacement of [3H]CP55940 from human CB1 receptor expressed in CHO cells incubated for 1 hr, Ki=0.0106μM 23072339
CHO Function assay > 0.1 nM 1 hr Inverse agonist activity at human recombinant CB1 receptor transfected in CHO cells assessed as reduction of [35S]GTPgammaS binding at > 0.1 nM after 1 hr by liquid scintillation spectrometry 23357307
N1E-115 Function assay 1 uM 5 mins Inverse agonist activity at CB1 receptor in mouse N1E-115 cells assessed as inhibition of WIN 55,212-2-induced ERK1/2 phosphorylation at 1 uM treated 5 mins prior to WIN 55,212-2 challenge by Western blot analysis 23357307
CHO Function assay Antagonist activity at human GPR18 transfected in CHO cells assessed as delta9-THC-induced beta-arrestin recruitment incubated 60 mins prior to delta9-THC addition by beta-arrestin translocation assay, IC50=10.1μM 23679955
HEK Function assay 1 hr Antagonist activity at human CB1 receptor overexpressed in HEK cells assessed as [35S]GTPgamma binding after 1 hr by liquid scintillation counting analysis, EC50=0.0015μM 24175572
CHOK1 Function assay 1 hr Displacement of [3H]CP55940 from human CB1 receptor expressed in CHOK1 cells after 1 hr by liquid scintillation counting analysis, Ki=0.0059μM 24175572
CHO Function assay 45 mins Antagonist activity at human CB1 receptor stably expressed in CHO cells co-expressing co-expressing Ga15/16 assessed as calcium current after 45 mins by fluo-4 AM assay, IC50=0.013μM 24445310
CHO Function assay 45 mins Antagonist activity at CB2 receptor (unknown origin) stably expressed in CHO cells co-expressing co-expressing Ga15/16 assessed as calcium current after 45 mins by fluo-4 AM assay, IC50=9.8μM 24445310
CHO-K1 Function assay 10 mins Antagonist activity at human CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP-55940-induced [35S]GTPgammaS binding incubated for 10 mins prior to CP-55940-challenge measured after 1 hr by beta counting, Ki=0.0016μM 24900484
HEK293 Function assay 60 mins Displacement of [3H]SR141716A form human CB1 receptor expressed in HEK293 cells after 60 mins by beta counting, Ki=0.0018μM 24900484
CHO-K1 Function assay 60 mins Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO-K1 cells after 60 mins by beta counting, Ki=0.522μM 24900484
CHO Function assay 2 hrs Displacement of [3H]CP55,940 from recombinant human CB1 receptor expressed in CHO cells after 2 hrs by liquid scintillation counting, Ki=0.0126μM 24900561
CHO Function assay 2 hrs Displacement of [3H]CP55,940 from recombinant human CB2 receptor expressed in CHO cells after 2 hrs by liquid scintillation counting, Ki=0.9μM 24900561
CHO Function assay 90 mins Agonist activity at GPR55 (unknown origin) expressed in CHO cells assessed as inhibition of LPI-induced beta-arrestin translocation after 90 mins by luminescence assay, EC50=2.01μM 24900561
RD-HGA16 Function assay Antagonist activity at CB1-OX1 heterodimer (unknown origin) expressed in RD-HGA16 cells assessed as inhibition of orexin A-induced calcium mobilization by fluorometric imaging plate reader analysis, Ke=0.001μM 24944734
RD-HGA16 Function assay Antagonist activity at CB1 receptor (unknown origin) expressed in RD-HGA16 cells assessed as inhibition of CP55940-induced calcium mobilization by fluorometric imaging plate reader analysis, Ke=0.0011μM 24944734
Sf9 Function assay 20 mins Inverse agonist activity at human CB1 receptor expressed in Sf9 cells coexpressing Gbeta1gamma2 and RSG4 assessed as degradation of [gamma-33P]GTP after 20 mins by steady-state GTPase assay, EC50=0.05μM 25096297
Sf9 Function assay 20 mins Inverse agonist activity at human CB1 receptor expressed in Sf9 cells coexpressing Gbeta1gamma2 and RSG4 assessed as degradation of [gamma-33P]GTP after 20 mins by steady-state GTPase assay, EC50=0.05012μM 25096297
CHO Function assay Antagonist activity against CB1R (unknown origin) CHO cells stably expressing Galpha16 assessed as inhibition of CP55940-induced increase in intracellular calcium level pre-treated 10 mins before CP55940 stimulation by microplate reader based assay, IC50=0.0135μM 26151231
CHO Function assay Antagonist activity against CB2R (unknown origin) CHO cells stably expressing Galpha16 assessed as inhibition of CP55940-induced increase in intracellular calcium level pre-treated 10 mins before CP55940 stimulation by microplate reader based assay, IC50=9.1μM 26151231
HEK293 Function assay Immediate antagonist/Inverse agonist activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as reversal of 1 uM CP55,940-induced inhibition of 5 uM forskolin-induced cAMP accumulation by kinetic cAMP assay 26203658
HEK293 Function assay 90 mins Displacement of [3H]-CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells after 90 mins by Competition binding assay, Kieq=0.012μM 26756097
HEK293 Function assay 90 mins Displacement of [3H]-CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells after 90 mins by Competition binding assay, Kieq=0.79μM 26756097
CHO-K1 Function assay Antagonist activity at human CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP55940-induced intracellular calcium mobilization by Calcein-4 AM-staining based FLIPR assay, Ke=0.0011μM 26827137
CHO Function assay 90 secs Inverse agonist activity at human CB1 receptor expressed in CHO cells assessed as increase in intracellular calcium mobilization after 90 secs by Calcein-4 AM-staining based FLIPR assay, EC50=0.005μM 26827137
SJ-GBM2 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells 29435139
A673 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells 29435139
SK-N-MC qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells 29435139
BT-37 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells 29435139
SK-N-SH qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells 29435139
NB1643 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells 29435139
LAN-5 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells 29435139
BT-12 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells 29435139
OHS-50 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells 29435139
RD qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells 29435139
A673 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for A673 cells) 29435139
SK-N-MC qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for SK-N-MC cells 29435139
DAOY qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for DAOY cells 29435139
TC32 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for TC32 cells 29435139
U-2 OS qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for U-2 OS cells 29435139
Rh41 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for Rh41 cells 29435139
Saos-2 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Confirmatory screen for Saos-2 cells 29435139
CHOK1 Function assay 90 mins Inverse agonist activity at C-terminally prolink-tagged mouse CB2 receptor expressed in CHOK1 cells harboring beta-galactosidase enzyme fused beta-arrestin assessed as increase in beta-arrestin recruitment after 90 mins by chemiluminescent assay, EC50=0.015μM 29939744
HEK293 Function assay Antagonist activity at human CB1 receptor expressed in HEK293 cells by GTPgammaS binding assay, Ke=0.0002μM 30077609
HEK293 Function assay 90 secs Inverse agonist activity at human CB1 receptor expressed in HEK293 cells co-expressing Galphaq16 assessed as inhibition of calcium mobilization after 90 secs by calcein-4 AAM dye-based FLIPR assay, EC50=0.586μM 30077609
HEK293 Function assay 30 mins Inverse agonist activity at human CB1 receptor expressed in HEK293 cells assessed as inhibition of forskolin-induced cAMP accumulation after 30 mins by HTRF assay, EC50=0.0041μM 30339387
CHO Function assay Displacement of [3H]-CP55940 from human recombinant cannabinoid CB1 receptor expressed in CHO cells by radioligand binding assay, Ki=0.143μM 31609608
CHO Function assay Agonist activity at human GPR55 expressed in CHO cells assessed as induction of LPI-induced beta-arrestin recruitment by beta-galactosidase enzyme fragment complementation method, EC50=2.01μM ChEMBL
CHO Function assay Agonist activity at human GPR18 expressed in CHO cells assessed as induction of beta-arrestin recruitment by beta-galactosidase enzyme fragment complementation method, EC50=10.1μM ChEMBL
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Solubility

In vitro
Batch:

DMSO : 92 mg/mL (198.36 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Ethanol : 50 mg/mL

Water : Insoluble

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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such
as vortex, ultrasound or hot water bath can be used to aid dissolving.

Chemical Information, Storage & Stability

Molecular Weight 463.79 Formula

C22H21Cl3N4O

 Storage (From the date of receipt)
CAS No. 168273-06-1 Download SDF Storage of Stock Solutions

Synonyms N/A Smiles CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl

Mechanism of Action

Features
Efficacious to induce weight reduction and improvements in cardiometabolic risk factors, however was withdrawn in 2009 due to severe depressive disorder and anxiety.
Targets/IC50/Ki
ACAT1
ACAT2
MmpL3
hCB1
(Cell-free assay)
13.6 nM
hCB2
(Cell-free assay)
1.64 μM
In vitro

Rimonabant (SR141716) dose-dependently reduces ACAT activity in Raw264.7macrophages with IC50 of 2.9 μM and isolated peritoneal macrophages. It inhibits ACATactivity in intact CHO-ACAT1 and CHO-ACAT2 cells and in cell-free assays with approximately equal efficiency with IC50 of 1.5 μM and 2.2 μM for CHO-ACAT1 and CHO-ACAT2, respectively. Consistent with ACAT inhibition, this compound treatment blocks ACAT dependent processes in macrophages, oxysterol-induced apoptosis and acetylated-LDL induced foam cell formation. It antagonizes the inhibitory effects of cannabinoid receptor agonists on both mouse vas deferens contractions and adenylyl cyclase activity in rat brain membranes in a concentration-dependent manner. The compound significantly reduces cell growth and induces cell death of human colorectal cancer cells (DLD-1, CaCo-2 and SW620). It is able to alter cell cycle distribution in all the cell lines tested. Particularly, Rimonabant produces a G2/M cell cycle arrest in DLD-1 cells without inducing apoptosis or necrosis.

Kinase Assay
Radioligand Binding Assay
Human CB1 and CB2 stably transfect HEK 293 cells and cell membrane is purified. 0.2-8 μg of the purified membrane is incubated with 0.75 nM [3H] CP55,940 and Rimonabant (SR141716) in the incubation buffer (50 mM Tris-HCl, 5 mM MgCl2, 1 mM EDTA, 0.3%BSA, pH 7.4). The non-specific binding is defined in the presence of 1 μM of CP55,940. The reactions are incubated for one and a half hours at 30 °C in Multiscreen. The reactions are terminated by manifold filtration and washed four times with ice-cold wash buffer (50mM Tris, pH 7.4, 0.25% BSA).The radioactivity bound to the filters is measured by Topcount. The IC50 is determined as the concentration of this compound required to inhibit 50% of the binding of [3H] CP55,940 and calculated by non-linear regression.
In vivo

Rimonabant (SR141716) is administered intraperitoneally or orally and potently and dose-dependently antagonizes classical pharmacological and behavioural effects of cannabinoid receptor agonists. In the mouse model of azoxymethane-induced colon carcinogenesis, it significantly decreased aberrant crypt foci (ACF) formation, which precedes colorectal cancer. This compound (10 mg/kg by gavage) is fed for 2 weeks to 3-month-old male obese Zucker rats as an impaired glucose tolerance model and for 10 weeks to 6-month-old male obese Zucker rats as a model of the metabolic syndrome. RANTES (Regulated upon Activation, Normal T cell Expressed, and Secreted) and MCP-1 (monocyte chemotactic protein-1) serum levels are increased in obese vs lean Zucker rats and significantly reduced by long-term treatment with it, which slows weight gain in rats with the metabolic syndrome. Neutrophils and monocytes are significantly increased in young and old obese vs lean Zucker rats and lowered by this compound. Platelet-bound fibrinogen is significantly enhanced in obese vs lean Zucker rats of both ages, and is reduced by it. Platelets from obese rats are more sensitive to thrombin-induced aggregation and adhesion to fibrinogen, which are both attenuated by Rimonabant therapy.

References
  • [4] https://pubmed.ncbi.nlm.nih.gov/19479993/
  • [5] https://pubmed.ncbi.nlm.nih.gov/18469848/
  • [6] https://pubmed.ncbi.nlm.nih.gov/17213845/
  • [7] https://pubmed.ncbi.nlm.nih.gov/30682372/

Applications

Methods Biomarkers Images PMID
Western blot CD44 / Lgr5 / CD133 / EpCAM β-catenin p-LRP6 / LRP6 / Lgr5
S3021-WB1
29354056
Immunofluorescence β-catenin Lgr5
S3021-IF1
29354056

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT00750347 Completed
Pain
University Hospital Clermont-Ferrand
 September 2008 Phase 1
NCT00656487 Completed
Cannabis Dependence|Cannabis Withdrawal
The Scripps Research Institute|National Institute on Drug Abuse (NIDA)
 April 30 2008 Phase 2
NCT00546325 Completed
Diabetes Mellitus Type 2
Sanofi
 October 2007 Phase 3
NCT00525681 Completed
Renal Transplantation
University of Oslo School of Pharmacy
 September 2007 Phase 4
NCT00584389 Terminated
Obesity
University of Surrey|European Foundation for the Study of Diabetes|Royal Surrey County Hospital NHS Foundation Trust
 July 2007 Phase 4
NCT01041170 Completed
Cannabis|Dependence
National Institute on Drug Abuse (NIDA)|National Institutes of Health Clinical Center (CC)
 April 16 2006 Phase 1

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Signaling Pathway Map