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Compound Detail

CHEMBL497

CLIOQUINOL
💊 Approved Drug
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💊 Approved Drug
Oc1c(I)cc(Cl)c2cccnc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL497
Name CLIOQUINOL
Phase Approved
Structure Type MOL
InChI Key QCDFBFJGMNKBDO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

4-stearylamino-phenyl-trimethylam. metilsulf. Clioquinol Clioquinol component of nystaform Iodochlorhydroxyquin Iodochlorhydroxyquinolone NSC-3531 NSC-74938 Oralcer Vioform
13
Targets
39
Activities
4
Assay Types
8
PK Parameters
20
Publications
9
Known Names
9
Indications
3
Mechanisms

Molecular Properties

305.5
MW (Da)
3.20
ALogP
2
HBA
1
HBD
33.1
PSA (Ų)
0.76
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1934
Availability Withdrawn
Chirality Achiral

Routes of Administration

Topical

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C9H5ClINO
MW 305.50
Aromatic Rings 2
Heavy Atoms 13
NP-Likeness -0.96

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Zinc chelating agent CHELATING AGENT Zinc ✓ ✓
Copper chelating agent CHELATING AGENT Copper ✓ ✓
Iron chelating agent CHELATING AGENT Iron ✓ ✓

Indications

Amebiasis Eczema Epilepsy Hodgkin Disease Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myeloid, Acute Lymphoma, Non-Hodgkin Multiple Myeloma Myelodysplastic Syndromes

ATC Classification

D08AH30
clioquinol
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS
D09AA10
clioquinol
Level 1: DERMATOLOGICALS
Level 2: MEDICATED DRESSINGS
G01AC02
clioquinol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
P01AA02
clioquinol
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS
P01AA52
clioquinol, combinations
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS
S02AA05
clioquinol
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Drug Warnings

Withdrawn
neurotoxicity
Implication in subacute myelo- optic neuropathy.
Country: France; Germany; United Kingdom; Japan; United States; Zimbabwe; Bangladesh; Philippines; Saudi Arabia; Ethiopia; Honduras   Year: 1973
Withdrawn
neurotoxicity
Neurotoxicity
Country: France; Germany; United Kingdom; Japan; United States; Zimbabwe; Bangladesh; Philippines; Saudi Arabia; Ethiopia; Honduras   Year: 1973
Withdrawn
neurotoxicity
Propensity to cause neurological disorders
Country: France; Germany; United Kingdom; Japan; United States; Zimbabwe; Bangladesh; Philippines; Saudi Arabia; Ethiopia; Honduras   Year: 1973

Activity Summary

IC50 30 meas. best 6.46
EC50 7 meas. best 5.75
Kd 1 meas. best 5.92
Ki 1 meas. best 5.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.46 5.4044 345.3 16
Matrix metalloproteinase-14
CHEMBL3869
 Kd 5.92 5.92 1200.0 1
Unchecked
CHEMBL612545
 EC50 5.75 5.0857 1800.0 7
Carbonic anhydrase 15
CHEMBL5973
 Ki 5.63 5.63 2330.0 1
Candida albicans
CHEMBL366
 IC50 5.58 5.58 2600.0 1
Metallo-beta-lactamase type 2
CHEMBL5465386
 IC50 5.52 5.52 3000.0 1
Catechol O-methyltransferase
CHEMBL2372
 IC50 5.32 5.32 4786.3 1
Spike glycoprotein
CHEMBL4662936
 IC50 5.25 5.25 5600.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 5.24 5.24 5790.0 1
No relevant target
CHEMBL2362975
 IC50 5.01 4.7 9720.0 2
Amyloid-beta precursor protein
CHEMBL2487
 IC50 5.01 4.6733 9800.0 3
Botulinum neurotoxin type A
CHEMBL5192
 IC50 4.69 4.69 20300.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 4.57 4.57 26900.0 1
Methionine aminopeptidase 2
CHEMBL3922
 IC50 4.09 4.09 80400.0 1
Methionine aminopeptidase 1
CHEMBL2474
 IC50 4.07 4.07 84700.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 3.69 10'5/M Homo sapiens
T1/2 136.0 hr Rattus norvegicus
T1/2 1.282 hr Rattus norvegicus
T1/2 42.4 hr Homo sapiens
T1/2 1.065 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 0.58 hr Rattus norvegicus
T1/2 0.5967 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 345.3 nM 6.46 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 391.7 nM 6.41 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 440.7 nM 6.36 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 475.1 nM 6.32 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 586.2 nM 6.23 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Matrix metalloproteinase-14 Kd = 1200.0 nM 5.92 Binding affinity to CMS sensor chip immobilized MMP-14 catalytic domain (unknown... 37094433
Unchecked EC50 = 1800.0 nM 5.75 Reversal of Zn-induced human soluble amyloid beta (1 to 42) aggregation after 30... 26396692
Carbonic anhydrase 15 Ki = 2330.0 nM 5.63 Inhibition of mouse recombinant carbonic anhydrase 15 by stopped-flow CO2 hydras... 18501600
Candida albicans IC50 = 2600.0 nM 5.58 Antibiofilm activity against Candida albicans SC5314 clinical isolates after 24 ... 28051303
Unchecked EC50 = 2920.0 nM 5.54 PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7K ce... -
Metallo-beta-lactamase type 2 IC50 = 3000.0 nM 5.52 Inhibition of C-terminal 6His-tagged full length NDM-1 (unknown origin) expresse... 37585683
Unchecked IC50 = 4300.0 nM 5.37 Inhibition of porcine heart malate dehydrogenase preincubated for 5 min followed... 34812616
Catechol O-methyltransferase IC50 = 4786.3 nM 5.32 Inhibition of Sprague-Dawley rat liver COMT after 10 mins using 0.05 uCi [14CH3]... 817025
Unchecked IC50 = 5399.2 nM 5.27 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
Unchecked IC50 = 5620.0 nM 5.25 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Spike glycoprotein IC50 = 5600.0 nM 5.25 Inhibition of SARS-COV2 ACE2 binding to spike glycoprotein S RBD domain preincub... 34812616
Kappa-type opioid receptor IC50 = 5790.0 nM 5.24 PUBCHEM_BIOASSAY: uHTS identification of small molecule antagonists of the kappa... -
Unchecked EC50 = 6300.0 nM 5.2 PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7 cel... -
Unchecked IC50 = 8073.0 nM 5.09 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 8560.0 nM 5.07 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -

Literature References

PubMed DOI Target Context # Activities
26473791 10.1021/acs.jmedchem.5b01222 Rattus norvegicus 22
37975824 10.1021/acs.jmedchem.3c01771 Cryptococcus neoformans 14
37975824 10.1021/acs.jmedchem.3c01771 Candida albicans 12
27316544 10.1016/j.bmc.2016.06.012 No relevant target 9
30553143 10.1016/j.ejmech.2018.12.013 Mus musculus 8
31753803 10.1016/j.bmc.2019.115182 5-demethoxyubiquinone hydroxylase, mitochondrial 7
27316544 10.1016/j.bmc.2016.06.012 Unchecked 7
37975824 10.1021/acs.jmedchem.3c01771 Candida tropicalis 6
37975824 10.1021/acs.jmedchem.3c01771 Candida parapsilosis 6
16581247 10.1016/j.bmcl.2006.03.026 Rattus norvegicus 6
23799643 10.1021/jm400567s Amyloid-beta precursor protein 6
7288822 10.1021/jm00141a011 Staphylococcus aureus 6
37975824 10.1021/acs.jmedchem.3c01771 [Candida] auris 6
37975824 10.1021/acs.jmedchem.3c01771 Pichia kudriavzevii 6
37975824 10.1021/acs.jmedchem.3c01771 Nakaseomyces glabratus 6
26068053 10.1021/acs.jmedchem.5b00272 SH-SY5Y 6
27316544 10.1016/j.bmc.2016.06.012 Amyloid-beta precursor protein 5
37975824 10.1021/acs.jmedchem.3c01771 Unchecked 5
26068053 10.1021/acs.jmedchem.5b00272 NON-PROTEIN TARGET 4
24387280 10.1021/jm4012164 Liver microsome 4

Data from ChEMBL 36 via Core Engine