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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1419
CHEMBL1419
Compound Name SIBUTRAMINE
ChEMBL Synonyms MERIDIA | BTS-54524 | BTS 54524 | REDUCTIL | SIBUTRAMINE HYDROCHLORIDE | SIBUTRAMINE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names REDUCTIL | MERIDIA
Molecular Formula C17H26ClN

Additional synonyms for CHEMBL1419 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)CC(N(C)C)C1(CCC1)c2ccc(Cl)cc2
Standard InChI InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8 ...
Download InChI
Standard InChI Key UNAANXDKBXWMLN-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • 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  • Withdrawn Drugs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


CHEMBL1419

Molecule Features

CHEMBL1419 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2010
Country Canada; China; European Union; Hong Kong; India; New Zealand; United States
Reason cardiovascular; increased risk of heart attack and stroke
Class Cardiotoxicity; Neurotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Monoamine transporter inhibitor Monoamine transporter FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
ObesityD009765EFO:0001073obesity4ATC
ClinicalTrials

Clinical Data

ClinicalTrials.gov SIBUTRAMINE
The Cochrane Collaboration SIBUTRAMINE

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 CHEMBL1419. 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
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 0.990
CHEMBL5023 p53-binding protein Mdm-2 Homo sapiens 0.834
CHEMBL5545 Sn1-specific diacylglycerol lipase alpha Homo sapiens 0.358

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 0.998
CHEMBL3401 Pregnane X receptor Homo sapiens 0.998
CHEMBL5023 p53-binding protein Mdm-2 Homo sapiens 0.976
CHEMBL228 Serotonin transporter Homo sapiens 0.541
CHEMBL5545 Sn1-specific diacylglycerol lipase alpha Homo sapiens 0.427
CHEMBL5493 Free fatty acid receptor 2 Homo sapiens 0.229

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
279.9 279.1754 4.74 5 3.24 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 0 0 1 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.69 5.47 3.24 1 19 0.75

Structural Alerts

There are no structural alerts for CHEMBL1419

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A08 - ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
A08A - ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
A08AA - Centrally acting antiobesity products
A08AA10 - sibutramine

ChemSpider ChemSpider:UNAANXDKBXWMLN-UHFFFAOYSA-N
PubChem SID: 174007250 SID: 49732001
Wikipedia Sibutramine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1419



ACToR 106650-56-0
BindingDB 84742
ChEBI 9137
ChemicalBook CB5708493
DrugBank DB01105
DrugCentral 2440
eMolecules 902461
EPA CompTox Dashboard DTXSID1023578
Guide to Pharmacology 2586
Human Metabolome Database HMDB0015237
IBM Patent System D3C3645FA37273257A19CBD104982DF8
KEGG Ligand C07247
LINCS LSM-5000
Mcule MCULE-6656338642
NIH Clinical Collection SAM001247105
Nikkaji J247.963J
PharmGKB PA451344
PubChem 5210
PubChem: Thomson Pharma 14750864
SureChEMBL SCHEMBL2955

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