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Compound Detail

CHEMBL1200596

CHLOROXINE
💊 Approved Drug
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💊 Approved Drug
Oc1c(Cl)cc(Cl)c2cccnc12

Basic Information

ChEMBL ID CHEMBL1200596
Name CHLOROXINE
Phase Approved
Structure Type MOL
InChI Key WDFKMLRRRCGAKS-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Capitrol Chloroxine NSC-3904
17
Targets
35
Activities
3
Assay Types
4
PK Parameters
20
Publications
3
Known Names
1
Mechanisms

Molecular Properties

214.1
MW (Da)
3.25
ALogP
2
HBA
1
HBD
33.1
PSA (Ų)
0.73
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1976
Availability Discontinued
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product
USAN Year 1977

Extended Properties

Molecular Formula C9H5Cl2NO
MW 214.05
Aromatic Rings 2
Heavy Atoms 13
NP-Likeness -0.86

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA

Activity Summary

IC50 28 meas. best 7.41
EC50 5 meas. best 6.83
Kd 2 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 7.41 6.2115 39.3 13
Streptokinase A
CHEMBL1293228
EC50 6.83 6.83 148.0 1
Streptococcus sp. 'group A'
CHEMBL612389
EC50 6.59 6.59 258.0 1
Candida albicans
CHEMBL366
IC50 5.92 5.8325 1200.0 4
Polyunsaturated fatty acid lipoxygenase ALOX12
CHEMBL3687
IC50 5.72 5.72 1900.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
IC50 5.62 5.62 2400.0 1
Matrix metalloproteinase-14
CHEMBL3869
Kd 5.62 5.62 2400.0 1
Streptococcus
CHEMBL612313
EC50 5.48 5.48 3306.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
IC50 5.44 5.44 3600.0 1
Replicase polyprotein 1ab
CHEMBL4523582
Kd 5.34 5.34 4600.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 5.34 5.34 4560.0 1
Metallo-beta-lactamase type 2
CHEMBL5465386
IC50 5.31 5.31 4900.0 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 5.14 5.14 7240.0 1
Botulinum neurotoxin type A
CHEMBL5192
IC50 4.94 4.94 11500.0 1
Unchecked
CHEMBL612545
EC50 4.89 4.89 12810.0 1
Matrix metalloproteinase-9
CHEMBL321
IC50 4.8 4.8 15900.0 1
Collagenase 3
CHEMBL280
IC50 4.71 4.71 19600.0 1
Matrix metalloproteinase-14
CHEMBL3869
IC50 4.59 4.59 25600.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15B
CHEMBL2457
IC50 4.55 4.55 28000.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 4.4 4.4 39800.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 67.7 hr Rattus norvegicus
T1/2 0.9167 hr Rattus norvegicus
T1/2 18.6 hr Homo sapiens
T1/2 0.815 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 39.34 nM 7.41 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 43.81 nM 7.36 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 47.46 nM 7.32 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 49.33 nM 7.31 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Unchecked IC50 = 62.74 nM 7.2 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Streptokinase A EC50 = 148.0 nM 6.83 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus sp. 'group A' EC50 = 258.0 nM 6.59 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Unchecked IC50 = 408.61 nM 6.39 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 495.2 nM 6.3 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 779.0 nM 6.11 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium... -
Candida albicans IC50 = 1200.0 nM 5.92 Antibiofilm activity against Candida albicans CAF2-1 after 48 hrs by Alamar blue... 28051303
Candida albicans IC50 = 1200.0 nM 5.92 Antibiofilm activity against fluconazole-resistant Candida albicans 29E clinical... 28051303
Candida albicans IC50 = 1200.0 nM 5.92 Antibiofilm activity against Candida albicans SC5314 after 48 hrs by Alamar blue... 28051303
Polyunsaturated fatty acid lipoxygenase ALOX12 IC50 = 1900.0 nM 5.72 Inhibition of human platelet-type N-terminally His6-tagged 12-lipoxygenase asses... 21739938
Unchecked IC50 = 2000.1 nM 5.7 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 2400.0 nM 5.62 Inhibition of human reticulocyte N-terminally His6-tagged 15-lipoxygenase-1 asse... 21739938
Matrix metalloproteinase-14 Kd = 2400.0 nM 5.62 Binding affinity to CMS sensor chip immobilized MMP-14 catalytic domain (unknown... 37094433
Candida albicans IC50 = 2700.0 nM 5.57 Antibiofilm activity against Candida albicans SC5314 clinical isolates after 24 ... 28051303
Streptococcus EC50 = 3306.0 nM 5.48 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 3600.0 nM 5.44 Inhibition of human 5-lipoxygenase assessed as conjugated diene product formatio... 21739938

Literature References

PubMed DOI Target Context # Activities
37585683 10.1021/acs.jmedchem.3c00171 Escherichia coli 12
37585683 10.1021/acs.jmedchem.3c00171 Klebsiella pneumoniae 10
34865870 10.1016/j.ejmech.2021.113975 Unchecked 9
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 5
28051303 10.1021/acs.jmedchem.6b01203 Candida albicans 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26789657 10.1021/acs.jmedchem.5b01696 Lanosterol 14-alpha demethylase 4
24387280 10.1021/jm4012164 Liver microsome 4
24387280 10.1021/jm4012164 Plasma 4
37094433 10.1016/j.bmc.2023.117289 Matrix metalloproteinase-14 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
35620927 10.1021/acs.jmedchem.2c00303 Replicase polyprotein 1ab 2
24387280 10.1021/jm4012164 No relevant target 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23445471 10.1021/jm301632e Human immunodeficiency virus type 1 integrase 2
23445471 10.1021/jm301632e Unchecked 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2

Data from ChEMBL 36 via Core Engine