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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL497
CHEMBL497
Compound Name CLIOQUINOL
ChEMBL Synonyms CLIOQUINOL | IODOCHLORHYDROXYQUIN | VIOFORM | DOMEFORM-HC | QUIN-O-CREME
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names DOMEFORM-HC | QUIN-O-CREME | VIOFORM
Molecular Formula C9H5ClINO

Additional synonyms for CHEMBL497 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Oc1c(I)cc(Cl)c2cccnc12
Standard InChI InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,1 ...
Download InChI
Standard InChI Key QCDFBFJGMNKBDO-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • 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  • Withdrawn Drugs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


CHEMBL497

Molecule Features

CHEMBL497 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First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1973
Country United Kingdom; United States; Germany; France; Japan
Reason Neurotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Copper chelating agent Copper PubMed PubMed
Iron chelating agent Iron PubMed PubMed
Zinc chelating agent Zinc PubMed PubMed

Clinical Data

ClinicalTrials.gov CLIOQUINOL
The Cochrane Collaboration CLIOQUINOL

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 CHEMBL497. 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
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.954
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.865
CHEMBL5443 Cell division cycle 7-related protein kinase Homo sapiens 0.792
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 0.764
CHEMBL4036 Cyclin-dependent kinase 5 Homo sapiens 0.693
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.669
CHEMBL2468 Death-associated protein kinase 3 Homo sapiens 0.655
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.622
CHEMBL4525 Serine/threonine-protein kinase 17A Homo sapiens 0.614
CHEMBL6166 Mitogen-activated protein kinase kinase kinase kinase 4 Homo sapiens 0.565
CHEMBL4575 Dual-specificity tyrosine-phosphorylation regulated kinase 3 Homo sapiens 0.565
CHEMBL2793 Casein kinase I alpha Homo sapiens 0.547
CHEMBL2595 Protein kinase C nu Homo sapiens 0.501
CHEMBL4576 Homeodomain-interacting protein kinase 2 Homo sapiens 0.481
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.478
CHEMBL5818 Serine/threonine-protein kinase PRKX Homo sapiens 0.420
CHEMBL5719 Cell division protein kinase 8 Homo sapiens 0.367
CHEMBL3055 Cyclin-dependent kinase 7 Homo sapiens 0.258
CHEMBL4101 cAMP-dependent protein kinase alpha-catalytic subunit Homo sapiens 0.217
CHEMBL5102 Vanilloid receptor Rattus norvegicus 0.214



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.996
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.991
CHEMBL2372 Catechol O-methyltransferase Rattus norvegicus 0.984
CHEMBL2285 ADAMTS5 Homo sapiens 0.960
CHEMBL3880 Heat shock protein HSP 90-alpha Homo sapiens 0.891
CHEMBL4576 Homeodomain-interacting protein kinase 2 Homo sapiens 0.799
CHEMBL5443 Cell division cycle 7-related protein kinase Homo sapiens 0.789
CHEMBL4036 Cyclin-dependent kinase 5 Homo sapiens 0.732
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.715
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.703
CHEMBL2793 Casein kinase I alpha Homo sapiens 0.699
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.525
CHEMBL2147 Serine/threonine-protein kinase PIM1 Homo sapiens 0.498
CHEMBL3055 Cyclin-dependent kinase 7 Homo sapiens 0.485
CHEMBL6166 Mitogen-activated protein kinase kinase kinase kinase 4 Homo sapiens 0.435
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 0.428
CHEMBL4525 Serine/threonine-protein kinase 17A Homo sapiens 0.423
CHEMBL4101 cAMP-dependent protein kinase alpha-catalytic subunit Homo sapiens 0.418
CHEMBL1075115 Dual specificity tyrosine-phosphorylation-regulated kinase 4 Homo sapiens 0.404
CHEMBL2468 Death-associated protein kinase 3 Homo sapiens 0.402

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
305.5 304.9104 3.02 0 33.12 ACID


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.32 7.23 4.17 2.47 2 13 0.76

Structural Alerts

There are 4 structural alerts for CHEMBL497. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D08 - ANTISEPTICS AND DISINFECTANTS
D08A - ANTISEPTICS AND DISINFECTANTS
D08AH - Quinoline derivatives
D08AH30 - clioquinol

G - GENITO URINARY SYSTEM AND SEX HORMONES
G01 - GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
G01A - ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
G01AC - Quinoline derivatives
G01AC02 - clioquinol

S - SENSORY ORGANS
S02 - OTOLOGICALS
S02A - ANTIINFECTIVES
S02AA - Antiinfectives
S02AA05 - clioquinol

D - DERMATOLOGICALS
D09 - MEDICATED DRESSINGS
D09A - MEDICATED DRESSINGS
D09AA - Medicated dressings with antiinfectives
D09AA10 - clioquinol

P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01A - AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01AA - Hydroxyquinoline derivatives
P01AA52 - clioquinol, combinations

P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01A - AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01AA - Hydroxyquinoline derivatives
P01AA02 - clioquinol

ChemSpider ChemSpider:QCDFBFJGMNKBDO-UHFFFAOYSA-N
PubChem SID: 104171297 SID: 11112285 SID: 124882179 SID: 124882180 SID: 144203967 SID: 144207489 SID: 170465019 SID: 17389542 SID: 24715134 SID: 26746922 SID: 85148761 SID: 855601
Wikipedia Clioquinol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL497



ACToR 130-26-7
Atlas clioquinol
BindingDB 32188
Brenda 199741 42598 75652
ChEBI 74460
DrugBank DB04815
DrugCentral 681
eMolecules 491690
EPA CompTox Dashboard DTXSID7022837
FDA SRS 7BHQ856EJ5
IBM Patent System 3C73A6534D779DD58E39363CED68C930
LINCS LSM-2186
Mcule MCULE-5389218452
MolPort MolPort-000-146-025
Nikkaji J5.432A
NMRShiftDB 30096614
PDBe CQL
PubChem 2788
PubChem: Drugs of the Future 56310601
PubChem: Thomson Pharma 14898627
SureChEMBL SCHEMBL3967
ZINC ZINC000006409735

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