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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL12713
CHEMBL12713
Compound Name SERTINDOLE
ChEMBL Synonyms SERLECT | SERTINDOLE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names SERLECT
Molecular Formula C24H26ClFN4O

Additional synonyms for CHEMBL12713 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Fc1ccc(cc1)n2cc(C3CCN(CCN4CCNC4=O)CC3)c5cc(Cl)ccc25
Standard InChI InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20- ...
Download InChI
Standard InChI Key GZKLJWGUPQBVJQ-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  • Withdrawn Drugs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


CHEMBL12713

Molecule Features

CHEMBL12713 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1998
Country United Kingdom; Germany; Italy; Ireland; Netherlands; European Union
Reason Arrhythmias and Sudden Cardiac Death (Arrhythmias and Sudden)

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
SCHIZOPHRENIAD012559EFO:0000692SCHIZOPHRENIA3ClinicalTrials
PSYCHOTIC DISORDERSD011618EFO:0005407PSYCHOSIS4ATC

Clinical Data

ClinicalTrials.gov SERTINDOLE
The Cochrane Collaboration SERTINDOLE

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 CHEMBL12713. 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
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 1.000
CHEMBL319 Alpha-1a adrenergic receptor Rattus norvegicus 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL3122 Alpha-1b adrenergic receptor Mesocricetus auratus 1.000
CHEMBL4892 Alpha-1a adrenergic receptor Bos taurus 1.000
CHEMBL324 Serotonin 2c (5-HT2c) receptor Rattus norvegicus 1.000
CHEMBL326 Alpha-1d adrenergic receptor Rattus norvegicus 1.000
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 1.000
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.999
CHEMBL3371 Serotonin 6 (5-HT6) receptor Homo sapiens 0.995
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.995
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 0.993
CHEMBL225 Serotonin 2c (5-HT2c) receptor Homo sapiens 0.971
CHEMBL231 Histamine H1 receptor Homo sapiens 0.888
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.725
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.519



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3122 Alpha-1b adrenergic receptor Mesocricetus auratus 1.000
CHEMBL324 Serotonin 2c (5-HT2c) receptor Rattus norvegicus 1.000
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL319 Alpha-1a adrenergic receptor Rattus norvegicus 1.000
CHEMBL4892 Alpha-1a adrenergic receptor Bos taurus 1.000
CHEMBL326 Alpha-1d adrenergic receptor Rattus norvegicus 1.000
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 1.000
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 1.000
CHEMBL3371 Serotonin 6 (5-HT6) receptor Homo sapiens 0.999
CHEMBL225 Serotonin 2c (5-HT2c) receptor Homo sapiens 0.999
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.998
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 0.996
CHEMBL231 Histamine H1 receptor Homo sapiens 0.990
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.990
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 0.982
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.962
CHEMBL234 Dopamine D3 receptor Homo sapiens 0.959
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.900

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
440.9 440.1779 4.68 5 40.51 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 5 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.98 3.67 2.47 3 31 0.63

Structural Alerts

There are no structural alerts for CHEMBL12713

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05A - ANTIPSYCHOTICS
N05AE - Indole derivatives
N05AE03 - sertindole

ChemSpider ChemSpider:GZKLJWGUPQBVJQ-UHFFFAOYSA-N
PubChem SID: 144206958 SID: 144206971 SID: 170465613
Wikipedia Sertindole

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL12713



ACToR 106516-24-9
BindingDB 50001786
ChEBI 9122
DrugBank DB06144
DrugCentral 2435
eMolecules 2730848
EPA CompTox Dashboard DTXSID6048967
FDA SRS GVV4Z879SP
Guide to Pharmacology 98
Human Metabolome Database HMDB0015618
IBM Patent System 3631021C5E434321F534C17117CCAF00
KEGG Ligand C07567
LINCS LSM-5765
MolPort MolPort-005-933-379
Nikkaji J380.356B
PharmGKB PA164784002
PubChem 60149
PubChem: Drugs of the Future 12014521
PubChem: Thomson Pharma 14905937
SureChEMBL SCHEMBL112092
ZINC ZINC000000538337

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