Compound Detail
CHEMBL111
RIMONABANT 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL111 |
| Name | RIMONABANT |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | JZCPYUJPEARBJL-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
18
Targets
259
Activities
4
Assay Types
30
PK Parameters
20
Publications
7
Known Names
17
Indications
1
Mechanisms
Molecular Properties
463.8
MW (Da)
5.94
ALogP
4
HBA
1
HBD
50.2
PSA (Ų)
0.52
QED
1
Ro5 Violations
4
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 2006 |
| Availability | Withdrawn |
| Chirality | Achiral |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Cannabinoid CB1 receptor antagonist | ANTAGONIST | Cannabinoid receptor 1 | ✓ | ✓ |
Indications
Obesity Arteriosclerosis Cardiovascular Diseases Coronary Artery Disease Diabetes Mellitus, Type 2 Fatty Liver Lipid Metabolism Disorders Metabolic Syndrome Prader-Willi Syndrome Prediabetic State Smoking Cessation Weight Loss Alcohol Drinking Spinal Cord Injuries Tobacco Use Disorder Marijuana Abuse Pain
ATC Classification
A08AX01
rimonabant
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
Drug Warnings
Withdrawn
psychiatric toxicity
psychiatric disorders, particularly depression
Withdrawn
psychiatric toxicity
psychiatric disorders, particularly depression
Activity Summary
Ki 146 meas. best 9.72
IC50 77 meas. best 8.87
EC50 26 meas. best 9.96
Kd 10 meas. best 9.6
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Cannabinoid receptor 1 CHEMBL218 | EC50 | 9.96 | 7.9269 | 0.1 | 16 |
| Cannabinoid receptor 1 CHEMBL3571 | EC50 | 9.77 | 6.51 | 0.2 | 3 |
| Cannabinoid receptor 1 CHEMBL218 | Ki | 9.72 | 8.2606 | 0.2 | 77 |
| Cavia porcellus CHEMBL369 | Kd | 9.6 | 9.6 | 0.2 | 1 |
| Cannabinoid receptor 1 CHEMBL3571 | Ki | 9.51 | 8.5585 | 0.3 | 13 |
| Rattus norvegicus CHEMBL376 | Ki | 8.96 | 8.96 | 1.1 | 1 |
| Cannabinoid receptor 2 CHEMBL253 | Ki | 8.96 | 6.1658 | 1.1 | 40 |
| Cannabinoid receptor 1 CHEMBL218 | IC50 | 8.87 | 8.0909 | 1.4 | 33 |
| Cannabinoid receptor 1 CHEMBL3037 | Ki | 8.82 | 8.5833 | 1.5 | 6 |
| Cannabinoid receptor 1 CHEMBL218 | Kd | 8.74 | 8.6171 | 1.8 | 7 |
| Cannabinoid receptor 1 CHEMBL3571 | IC50 | 8.72 | 8.0031 | 1.9 | 16 |
| Cannabinoid receptor 2 CHEMBL253 | IC50 | 8.72 | 5.9137 | 1.9 | 19 |
| Mus musculus CHEMBL375 | Kd | 8.7 | 8.7 | 2.0 | 1 |
| Cytochrome P450 2C9 CHEMBL3397 | IC50 | 8.28 | 8.28 | 5.3 | 1 |
| Cannabinoid receptor 2 CHEMBL5373 | EC50 | 7.82 | 7.82 | 15.0 | 1 |
| Cannabinoid receptor 1 CHEMBL3037 | IC50 | 7.6 | 7.6 | 25.0 | 2 |
| Cannabinoid receptor CHEMBL2111385 | Ki | 7.37 | 7.37 | 43.0 | 1 |
| Unchecked CHEMBL612545 | Ki | 7.18 | 7.18 | 65.8 | 1 |
| Cannabinoid receptor 1 CHEMBL3037 | Kd | 6.72 | 6.72 | 190.6 | 1 |
| Cannabinoid receptor 2 CHEMBL5373 | Ki | 6.43 | 6.118 | 375.0 | 5 |
| Multidrug resistance-associated protein 1 CHEMBL3004 | Ki | 5.85 | 5.85 | 1400.0 | 1 |
| G-protein coupled receptor 55 CHEMBL1075322 | EC50 | 5.7 | 5.7 | 2010.0 | 2 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | IC50 | 5.55 | 5.435 | 2790.0 | 2 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | Ki | 5.4 | 5.4 | 4000.0 | 1 |
| Muscarinic acetylcholine receptor M2 CHEMBL211 | IC50 | 5.21 | 5.21 | 6215.2 | 1 |
| Cannabinoid receptor 1 CHEMBL3037 | EC50 | 5.05 | 5.05 | 8990.0 | 1 |
| N-arachidonyl glycine receptor CHEMBL2384898 | IC50 | 5.0 | 5.0 | 10100.0 | 1 |
| N-arachidonyl glycine receptor CHEMBL2384898 | EC50 | 5.0 | 5.0 | 10100.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 4.79 | 4.79 | 16170.0 | 1 |
| Bile salt export pump CHEMBL6020 | IC50 | 4.6 | 4.6 | 25000.0 | 1 |
| Cannabinoid receptor 2 CHEMBL253 | EC50 | 4.51 | 4.51 | 31210.0 | 1 |
| Rattus norvegicus CHEMBL376 | EC50 | 4.25 | 4.25 | 56300.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 41200.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 41200.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 556.67 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 209.83 | ng.hr.mL-1 | Rattus norvegicus |
| CL | 9000.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 1700.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 41.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 159.0 | mL.min-1.g-1 | Rattus norvegicus |
| CL | 3.22 | mL.min-1.g-1 | Mus musculus |
| CL | 1.09 | mL.min-1.g-1 | Homo sapiens |
| CL | 82.4 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 6.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 69.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 6.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 6.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 46.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 17.0 | mL.min-1.kg-1 | Rattus norvegicus |
| Cmax | 4139.72 | nM | Rattus norvegicus |
| Cmax | 4139.72 | nM | Rattus norvegicus |
| Cmax | 625.27 | nM | Rattus norvegicus |
| Cmax | 646.83 | nM | Rattus norvegicus |
| Cmax | 526.09 | nM | Rattus norvegicus |
| Cmax | 400.0 | nM | Homo sapiens |
| F | 53.1 | % | Rattus norvegicus |
| F | 12.0 | % | Rattus norvegicus |
| Fu | 0.0005 | - | Homo sapiens |
| Fu | 0.0006 | - | Macaca fascicularis |
| Fu | 0.0005 | - | Canis lupus familiaris |
| Fu | 0.0004 | - | Cavia porcellus |
| Fu | 0.0004 | - | Mus musculus |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine