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Compound Detail

CHEMBL220360

TARANABANT
🧪 Phase III
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🧪 Phase III
C[C@H](NC(=O)C(C)(C)Oc1ccc(C(F)(F)F)cn1)[C@@H](Cc1ccc(Cl)cc1)c1cccc(C#N)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL220360
Name TARANABANT
Phase Phase III
Structure Type MOL
InChI Key QLYKJCMUNUWAGO-GAJHUEQPSA-N

Known Names

L-796568 Mk-0364 MK-0634 Mk0364 MK0634 Taranabant
6
Targets
32
Activities
3
Assay Types
20
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

516.0
MW (Da)
6.31
ALogP
4
HBA
1
HBD
75.0
PSA (Ų)
0.38
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -nab-
USAN Year 2006

Extended Properties

Molecular Formula C27H25ClF3N3O2
MW 515.96
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -1.29

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cannabinoid CB1 receptor inverse agonist INVERSE AGONIST Cannabinoid receptor 1 ✓ ✓

Indications

Diabetes Mellitus, Type 2 Obesity Tobacco Use Disorder Urinary Incontinence

Activity Summary

IC50 28 meas. best 10.03
EC50 2 meas. best 8.62
Ki 2 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 1
CHEMBL218
 IC50 10.03 9.1547 0.1 19
Cannabinoid receptor 1
CHEMBL218
 Ki 9.52 9.52 0.3 1
Cannabinoid receptor 1
CHEMBL3571
 IC50 9.52 9.295 0.3 2
Cytochrome P450 2D6
CHEMBL289
 IC50 9.23 9.23 0.6 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 9.03 9.03 0.9 1
Cannabinoid receptor 1
CHEMBL218
 EC50 8.62 8.62 2.4 2
Cannabinoid receptor 2
CHEMBL253
 IC50 6.54 6.3875 285.0 4
Cannabinoid receptor 2
CHEMBL253
 Ki 6.54 6.54 290.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.85 4.85 14200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1394.0 ng.hr.mL-1 Rattus norvegicus
AUC 412.5 ng.hr.mL-1 Rattus norvegicus
CL 33.0 mL.min-1.kg-1 Rattus norvegicus
CL 40.83 mL.min-1.kg-1 Rattus norvegicus
Cmax 490.0 nM Rattus norvegicus
Cmax 697.73 nM Rattus norvegicus
Cmax 910.92 nM Rattus norvegicus
F 31.0 % Canis lupus familiaris
F 31.0 % Macaca mulatta
F 74.0 % Rattus norvegicus
F 74.0 % Rattus norvegicus
F 67.6 % Rattus norvegicus
T1/2 14.0 hr Canis lupus familiaris
T1/2 3.6 hr Macaca mulatta
T1/2 2.7 hr Rattus norvegicus
T1/2 2.7 hr Rattus norvegicus
T1/2 14.8 hr Rattus norvegicus
T1/2 2.76 hr Rattus norvegicus
T1/2 72.0 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 1 IC50 = 0.094 nM 10.03 Displacement of [3H]SR-141716 from human wild type CB1R expressed in CHO cells 18333607
Cannabinoid receptor 1 IC50 = 0.29 nM 9.54 Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells 18570365
Cannabinoid receptor 1 Ki = 0.3 nM 9.52 Displacement of [3H]rimonabant from human CB1 receptor expressed in HEK293 cells... 19520572
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inhibition of radiolabeled CP5549 binding to human Cannabinoid receptor 1 expres... 31497963
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inhibition of CB1 receptor (unknown origin) -
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Displacement of [3H]SR141716A from rat brain CB1 receptor at pH 7.4 after 1 hr b... 21741835
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Binding affinity to human CB1 receptor 20483606
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inhibition of cannabinoid CB1 receptor 20423086
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inhibition of human CB1 receptor 20096577
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Displacement of [3H]CP-55940 from recombinant human CB1 receptor expressed in CH... 19632830
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inverse agonist activity at cannabinoid CB1 receptor 19328684
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells 18335976
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Displacement of [3H]CP-55940 from human recombinant CB1R expressed in CHO cells 17608398
Cannabinoid receptor 1 IC50 = 0.3 nM 9.52 Inhibition of [3H]CP-55940 binding to human recombinant CB1 receptor in CHO cell... 17181138
Cytochrome P450 2D6 IC50 = 0.59 nM 9.23 Inhibition of CYP2D6 in human liver microsomes after 30 mins 20673729
Cannabinoid receptor 1 IC50 = 0.74 nM 9.13 Displacement of [3H]CP-55940 from human wild type CB1R expressed in CHO cells 18333607
Cannabinoid receptor 1 IC50 = 0.74 nM 9.13 Displacement of [3H]CP55490 from human recombinant cannabinoid CB1 receptor expr... 20643546
Cannabinoid receptor 1 IC50 = 0.86 nM 9.07 Displacement of [3H]CP-55940 from CB1 receptor in Sprague-Dawley rat cerebellum ... 18954042
Cytochrome P450 2C9 IC50 = 0.93 nM 9.03 Inhibition of CYP2C9 in human liver microsomes after 30 mins 20673729
Cannabinoid receptor 1 IC50 = 1.2 nM 8.92 Displacement of [3H]CP-55940 from human CB1R K192L mutant expressed in CHO cells 18333607

Literature References

PubMed DOI Target Context # Activities
20673729 10.1016/j.bmc.2010.07.013 Rattus norvegicus 12
17181138 10.1021/jm060978s Rattus norvegicus 8
18333607 10.1021/jm7014974 Cannabinoid receptor 1 7
19527048 10.1021/jm900179y Mus musculus 6
18333607 10.1021/jm7014974 Unchecked 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20096577 10.1016/j.bmcl.2009.12.065 Rattus norvegicus 4
18570365 10.1021/jm800219f Rattus norvegicus 4
17181138 10.1021/jm060978s Cannabinoid receptor 1 3
19632830 10.1016/j.bmcl.2009.07.046 Cannabinoid receptor 1 2
20673729 10.1016/j.bmc.2010.07.013 ADMET 2
19328684 10.1016/j.bmcl.2009.03.005 Rattus norvegicus 2
20423086 10.1021/jm100023j Cannabinoid receptor 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
20483606 10.1016/j.bmcl.2010.04.071 Rattus norvegicus 2
20423086 10.1021/jm100023j Cannabinoid receptor 2 2
17181138 10.1021/jm060978s Rhesus monkey 2
17181138 10.1021/jm060978s Canis familiaris 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine