RIMONABANT

Search structure
Synonyms:
Status: Approved (2006) Withdrawn (2008)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: A08AX01
UNII: RML78EN3XE

Structure
InChI Key JZCPYUJPEARBJL-UHFFFAOYSA-N
Smile Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H21Cl3N4O
Molecular Weight 463.8
AlogP 5.94
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 50.16
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 30.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Cannabinoid CB1 receptor antagonist
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 5.3 - - -
Enzyme Hydrolase
- - - -
Enzyme Transferase
- - - - 5.55
Enzyme
- 5.3 - -
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -15.68-3.97
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 2790-4800 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor
0.11-586 1.35-158.49 1.8-2.57 0.19-143 0-100
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Lysophosphatidylinositol receptor
2010-2010 - - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- 6215.16 - - -
Membrane receptor Family A G protein-coupled receptor
0.11-586 1.35-158.49 1.8-2.57 0.19-143 0-100
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 25000 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- - - 1400

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cardiovascular Diseases 3 D002318 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Fatty Liver 3 D005234 ClinicalTrials
Prader-Willi Syndrome 3 D011218 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Weight Loss 3 D015431 ClinicalTrials
Coronary Artery Disease 3 D003324 ClinicalTrials
Arteriosclerosis 3 D001161 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Smoking Cessation 3 D016540 ClinicalTrials
Prediabetic State 3 D011236 ClinicalTrials
Alcohol Drinking 2 D000428 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Spinal Cord Injuries 2 D013119 ClinicalTrials
Pain 1 D010146 ClinicalTrials
Marijuana Abuse 1 D002189 ClinicalTrials

Related Entries

Scaffolds

Cross References

Resources Reference
CAS NUMBER 168273-06-1
ChEBI 34967
ChEMBL CHEMBL111
DrugBank DB06155
DrugCentral 4150
EPA CompTox DTXSID3046453
FDA SRS RML78EN3XE
Human Metabolome Database HMDB15623
Guide to Pharmacology 743
KEGG C14319
PDB AY6
PharmGKB PA152407999
PubChem 104850
SureChEMBL SCHEMBL38637
ZINC ZINC000001540228
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