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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL111
CHEMBL111
Compound Name RIMONABANT
ChEMBL Synonyms RIMONABANT | SR-14171 | ACOMPLIA | SR-141716A | SR141716
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names ACOMPLIA
Molecular Formula C22H21Cl3N4O

Additional synonyms for CHEMBL111 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1c(nn(c2ccc(Cl)cc2Cl)c1c3ccc(Cl)cc3)C(=O)NN4CCCCC4
Standard InChI InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26 ...
Download InChI
Standard InChI Key JZCPYUJPEARBJL-UHFFFAOYSA-N

Sources

  • British National Formulary
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL111

Molecule Features

CHEMBL111 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2008
Country European Union; Never approved in the United States
Reason Psychiatric effects, especially depression
Class Psychiatric toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cannabinoid CB1 receptor antagonist Cannabinoid CB1 receptor PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Prediabetic StateD011236EFO:1001121prediabetes syndrome3ClinicalTrials
Alcohol DrinkingD000428EFO:0004329alcohol drinking2ClinicalTrials
Prader-Willi SyndromeD011218Orphanet:739Prader-Willi syndrome3ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease3ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus3ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease3ClinicalTrials
Lipid Metabolism DisordersD052439Orphanet:309005Disorder of lipid metabolism3ClinicalTrials
Fatty LiverD005234HP:0001397Hepatic steatosis3ClinicalTrials
ObesityD009765EFO:0001073obesity3ClinicalTrials
Marijuana AbuseD002189EFO:0004218marijuana dependence1ClinicalTrials
Metabolic SyndromeD024821EFO:0000195metabolic syndrome3ClinicalTrials
PainD010146EFO:0003843pain1ClinicalTrials
Smoking CessationD016540EFO:0004319smoking cessation3ClinicalTrials
Tobacco Use DisorderD014029EFO:0003768nicotine dependence2ClinicalTrials

Clinical Data

ClinicalTrials.gov RIMONABANT
The Cochrane Collaboration RIMONABANT

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL111. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL4552 Peripheral-type benzodiazepine receptor Rattus norvegicus 0.816
CHEMBL244 Coagulation factor X Homo sapiens 0.396
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.394



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL4552 Peripheral-type benzodiazepine receptor Rattus norvegicus 0.883
CHEMBL244 Coagulation factor X Homo sapiens 0.678
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.322

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
463.8 462.0781 5.94 4 50.16 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 1 5 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.31 3.22 4.84 4.84 3 30 0.52

Structural Alerts

There are 2 structural alerts for CHEMBL111. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A08 - ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
A08A - ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
A08AX - Other antiobesity drugs
A08AX01 - rimonabant

ChemSpider ChemSpider:JZCPYUJPEARBJL-UHFFFAOYSA-N
PubChem SID: 144205753 SID: 170465599 SID: 26757994
Wikipedia Rimonabant

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL111



ACToR 168273-06-1
BindingDB 21278
ChEBI 34967
ChemicalBook CB4129374
DrugBank DB06155
DrugCentral 4150
eMolecules 2728948
EPA CompTox Dashboard DTXSID3046453
FDA SRS RML78EN3XE
Guide to Pharmacology 743
Human Metabolome Database HMDB0015623
IBM Patent System 404AD94F36E63BCC8E934DC9DC6922B4
KEGG Ligand C14319
LINCS LSM-36994
Mcule MCULE-7311256045
MolPort MolPort-003-850-185
Nikkaji J649.754C
PharmGKB PA152407999
PubChem 104850
PubChem: Drugs of the Future 12014928
PubChem: Thomson Pharma 14809274
Selleck rimonabant-sr141716
SureChEMBL SCHEMBL38637
ZINC ZINC000001540228

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/JZCPYUJPEARBJL-UHFFFAOYSA-N spacer
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