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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL296419
CHEMBL296419
Compound Name ASTEMIZOLE
ChEMBL Synonyms POLLON-EZE | R 43,512 | HISMANAL | GNF-Pf-2461 | ASTEMIZOLE | [3H]-Astemizole
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names HISMANAL | POLLON-EZE
Molecular Formula C28H31FN4O

Additional synonyms for CHEMBL296419 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1ccc(CCN2CCC(CC2)Nc3nc4ccccc4n3Cc5ccc(F)cc5)cc1
Standard InChI InChI=1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15- ...
Download InChI
Standard InChI Key GXDALQBWZGODGZ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Harvard Malaria Screening
  • Novartis Malaria Screening
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL296419

Molecule Features

CHEMBL296419 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1999
Country United States; Malasia
Reason Fatal arrhythmia; Drug Interaction
Class Cardiotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Histamine H1 receptor antagonist Histamine H1 receptor PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
HypersensitivityD006967EFO:0003785allergy4ATC

Clinical Data

ClinicalTrials.gov ASTEMIZOLE
The Cochrane Collaboration ASTEMIZOLE

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 CHEMBL296419. 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
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 1.000
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 1.000
CHEMBL264 Histamine H3 receptor Homo sapiens 0.991
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.973
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.881
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.636
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.497
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.488
CHEMBL287 Sigma opioid receptor Homo sapiens 0.420
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.395
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 0.228



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL1792 Somatostatin receptor 5 Homo sapiens 1.000
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 1.000
CHEMBL1941 Histamine H2 receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 0.998
CHEMBL264 Histamine H3 receptor Homo sapiens 0.992
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.979
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.957
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.946
CHEMBL324 Serotonin 2c (5-HT2c) receptor Rattus norvegicus 0.840
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.788
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.677
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.620
CHEMBL313 Serotonin transporter Rattus norvegicus 0.569
CHEMBL4777 Neuropeptide Y receptor type 1 Homo sapiens 0.428
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.347
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.333
CHEMBL287 Sigma opioid receptor Homo sapiens 0.309
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 0.305
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 0.220

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
458.6 458.2482 5.35 8 42.32 BASE


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.68 5.52 4.12 4 34 0.39

Structural Alerts

There are no structural alerts for CHEMBL296419

Compound Cross References

ATC R - RESPIRATORY SYSTEM
R06 - ANTIHISTAMINES FOR SYSTEMIC USE
R06A - ANTIHISTAMINES FOR SYSTEMIC USE
R06AX - Other antihistamines for systemic use
R06AX11 - astemizole

ChemSpider ChemSpider:GXDALQBWZGODGZ-UHFFFAOYSA-N
PubChem SID: 104171329 SID: 11112828 SID: 124882660 SID: 124882662 SID: 144204231 SID: 144207293 SID: 170465888 SID: 26746979 SID: 26751496 SID: 26751497 SID: 56422418 SID: 855746
Wikipedia Astemizole

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL296419



ACToR 68844-77-9
BindingDB 24226
Brenda 66181
ChEBI 2896
DrugBank DB00637
DrugCentral 249
eMolecules 534476
EPA CompTox Dashboard DTXSID9020110
FDA SRS 7HU6337315
Guide to Pharmacology 2603
Human Metabolome Database HMDB0014775
IBM Patent System 3D7D711B7D0695BE4A3381BE207E1D1B
KEGG Ligand C06832
LINCS LSM-5502
Mcule MCULE-9080712110
MolPort MolPort-003-666-765
Nikkaji J18.595G
PharmGKB PA448498
PubChem 2247
PubChem: Drugs of the Future 12013338
PubChem: Thomson Pharma 14760289
SureChEMBL SCHEMBL4385
ZINC ZINC000000601274

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