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Compound Detail

CHEMBL76

CHLOROQUINE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12

Basic Information

ChEMBL ID CHEMBL76
Name CHLOROQUINE
Phase Approved
Structure Type MOL
InChI Key WHTVZRBIWZFKQO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Chloroquine Cloroquina NSC-187208
99
Targets
2,267
Activities
4
Assay Types
30
PK Parameters
20
Publications
3
Known Names
20
Indications

Molecular Properties

319.9
MW (Da)
4.81
ALogP
3
HBA
1
HBD
28.2
PSA (Ų)
0.76
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1949
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product

Extended Properties

Molecular Formula C18H26ClN3
MW 319.88
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.27

Indications

Malaria Arthritis, Rheumatoid Glioblastoma Malaria, Falciparum Malaria, Vivax Pregnancy Severe Acute Respiratory Syndrome Acquired Immunodeficiency Syndrome Anemia, Sickle Cell Brain Diseases Breast Neoplasms HIV Infections Influenza, Human Lupus Erythematosus, Systemic Multiple Myeloma Carcinoma, Intraductal, Noninfiltrating Gliosarcoma Neoplasms Pancreatic Neoplasms Severe Dengue

ATC Classification

P01BA01
chloroquine
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 2,029 meas. best 10.52
EC50 221 meas. best 10.02
Ki 12 meas. best 7.1
Kd 5 meas. best 5.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 10.52 7.1771 0.0 1712
Unchecked
CHEMBL612545
IC50 10.52 5.1258 0.0 38
Plasmodium falciparum
CHEMBL364
EC50 10.02 7.1428 0.1 148
Plasmodium vivax
CHEMBL613013
IC50 8.26 6.8908 5.5 24
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.11 5.3983 7.8 12
Plasmodium knowlesi
CHEMBL613011
EC50 8.0 7.34 10.0 2
Plasmodium knowlesi
CHEMBL613011
IC50 8.0 8.0 10.0 1
Plasmodium malariae
CHEMBL613257
IC50 7.85 7.37 14.0 2
Unchecked
CHEMBL612545
EC50 7.75 7.355 18.0 2
Cryptosporidium parvum
CHEMBL612855
IC50 7.57 7.57 27.0 1
Dihydrofolate reductase
CHEMBL1075051
IC50 7.52 7.5167 30.1 3
A549
CHEMBL392
IC50 7.4 5.7 40.0 2
Plasmodium berghei
CHEMBL612653
IC50 7.22 5.69 60.0 3
MRC5
CHEMBL614181
IC50 7.19 5.0075 64.0 4
Histidine-rich protein PFHRP-II
CHEMBL1923
IC50 7.12 4.9289 76.5 9
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.1 7.1 79.4 1
Plasmodium yoelii
CHEMBL612889
IC50 6.97 5.9533 106.0 3
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.96 5.3543 110.0 7
Spike glycoprotein
CHEMBL4662936
IC50 6.8 6.8 160.0 1
Hemozoin
CHEMBL613898
IC50 6.75 4.7442 180.0 12
L6
CHEMBL614793
IC50 6.72 4.4491 188.5 11
Plasmodium falciparum K1
CHEMBL612856
IC50 6.63 6.63 235.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
IC50 6.57 6.57 270.0 2
Human coronavirus OC43
CHEMBL5209665
EC50 6.48 6.48 330.0 1
Giardia intestinalis
CHEMBL612652
IC50 6.4 6.4 401.0 1
HEK293
CHEMBL614818
IC50 6.31 4.942 490.0 5
Sigma intracellular receptor 2
CHEMBL4105907
Ki 6.3 6.3 501.2 1
Zika virus
CHEMBL4296612
EC50 6.02 5.2413 950.0 8
Angiotensin-converting enzyme 2
CHEMBL3736
IC50 5.95 5.95 1130.0 1
SARS-CoV-2
CHEMBL4303835
EC50 5.95 5.5267 1130.0 6
SARS-CoV-2
CHEMBL4303835
IC50 5.95 5.1386 1130.0 7
SARS-CoV
CHEMBL4303836
EC50 5.95 5.5767 1130.0 3
Human coronavirus 229E
CHEMBL613837
EC50 5.89 5.6167 1300.0 3
Ribosyldihydronicotinamide dehydrogenase [quinone]
CHEMBL3959
IC50 5.82 5.82 1500.0 1
BK polyomavirus
CHEMBL4888480
EC50 5.77 5.77 1700.0 1
Hepatocyte
CHEMBL613289
IC50 5.72 5.72 1900.0 1
Riboflavin-binding protein
CHEMBL1944489
Kd 5.68 5.68 2100.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.6 5.6 2500.0 4
Middle East respiratory syndrome-related coronavirus
CHEMBL4296578
EC50 5.52 5.52 3000.0 1
BEAS-2B
CHEMBL4296403
IC50 5.51 5.51 3070.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 5.5 5.31 3162.3 2
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.48 5.48 3311.3 1
ADMET
CHEMBL612558
IC50 5.46 4.8371 3460.0 7
MIA PaCa-2
CHEMBL614725
IC50 5.46 5.46 3500.0 1
HT-29
CHEMBL384
IC50 5.44 5.44 3600.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 5.42 5.42 3810.0 1
Heme
CHEMBL4651321
Kd 5.4 5.4 4000.0 1
Major prion protein
CHEMBL4869
EC50 5.4 5.4 4000.0 1
ScN2a
CHEMBL613872
EC50 5.4 5.4 4000.0 1
Usutu virus
CHEMBL4296609
EC50 5.37 5.2567 4240.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 37489.94 ng.hr.mL-1 Homo sapiens
AUC 39185.3 ng.hr.mL-1 Homo sapiens
AUC 844.16 ng.hr.mL-1 Mus musculus
AUC 50028.0 ng.hr.mL-1 Homo sapiens
AUC 35659.0 ng.hr.mL-1 Homo sapiens
AUC 47545.0 ng.hr.mL-1 Homo sapiens
AUC 59431.0 ng.hr.mL-1 Homo sapiens
AUC 41255.0 ng.hr.mL-1 Homo sapiens
AUC 23876.0 ng.hr.mL-1 Homo sapiens
AUC 31835.0 ng.hr.mL-1 Homo sapiens
AUC 39793.0 ng.hr.mL-1 Homo sapiens
AUC 30.15 ng.hr.mL-1 Rattus norvegicus
AUClast - - Plasmodium berghei
CL 4.1 mL.min-1.kg-1 Homo sapiens
CL 1.8 mL.min-1.kg-1 Homo sapiens
CL 4.1 mL.min-1.kg-1 Homo sapiens
CL 4.1 mL.min-1.kg-1 Homo sapiens
CL 0.15 L/hr Rattus norvegicus
CL 17.0 mL.min-1.kg-1 Mus musculus
Cmax 240.0 nM Homo sapiens
Cmax 444.3 nM Mus musculus
Cmax 1544.33 nM Homo sapiens
Cmax 1234.84 nM Homo sapiens
Cmax 925.35 nM Homo sapiens
Cmax 1175.44 nM Homo sapiens
Cmax 581.47 nM Homo sapiens
Cmax 434.54 nM Homo sapiens
Cmax 578.34 nM Homo sapiens
Cmax 725.27 nM Homo sapiens
Cmax 16346.76 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.03 nM 10.52 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 19269069
Unchecked IC50 = 0.03 nM 10.52 Inhibition of V-ATPase activity in lysosomes of human PC-3 cells 38295689
Plasmodium falciparum IC50 = 0.04 nM 10.4 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D10 19572738
Plasmodium falciparum IC50 = 0.06 nM 10.22 Intrinsic equimolar activity against Plasmodium falciparum W2 Indochina relative... 3279208
Plasmodium falciparum EC50 = 0.095 nM 10.02 Antimalarial activity against erythrocytic stage of chloroquine and pyrimethamin... 23517371
Plasmodium falciparum IC50 = 0.11 nM 9.96 Antiplasmodial activity against Plasmodium falciparum FcB1/Columbia infected in ... 25659770
Plasmodium falciparum EC50 = 0.67 nM 9.17 Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as inhibition... 24900279
Plasmodium falciparum IC50 = 0.97 nM 9.01 Intrinsic equimolar activity against Plasmodium falciparum D6 (Sierra Leone) rel... 3279208
Plasmodium falciparum IC50 = 1.4 nM 8.85 Antiplasmodial activity chloroquine-sensitive Plasmodium falciparum 3D7 infected... 22459876
Unchecked IC50 = 1.9 nM 8.72 Inhibition of beta-hematin formation assessed as equivalents of drug relative to... 21875063
Plasmodium falciparum EC50 = 2.0 nM 8.7 Antimalarial activity against Plasmodium falciparum 3D7 assessed as reduction in... 37163950
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antimalarial activity against Chloroquine sensitive Plasmodium falciparum 3D7 as... 37484560
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum NF54... 23320609
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D10 21705220
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 21705220
Plasmodium falciparum IC50 = 2.4 nM 8.62 Antimalarial activity against drug-sensitive Plasmodium falciparum 3D7 after 24 ... 17548196
Plasmodium falciparum EC50 = 2.426 nM 8.62 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antiplasmodial activity against Plasmodium falciparum NF54 erythrocytic stages a... 33002847
Plasmodium falciparum IC50 = 3.02 nM 8.52 Antiplasmodial activity against Plasmodium falciparum NF54 erythrocytic stages a... 33002847
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antimalarial activity against erythrocytic stage of chloroquine-sensitive Plasmo... 37696205

Literature References

PubMed DOI Target Context # Activities
20086162 10.1128/aac.01269-09 Homo sapiens 32
25137549 10.1021/jm5009693 Plasmodium falciparum 30
20329733 10.1021/jm9018383 Plasmodium falciparum 27
37163950 10.1016/j.ejmech.2023.115458 Plasmodium falciparum 24
33289551 10.1021/acs.jmedchem.0c00894 Nuclear receptor subfamily 4 group A member 2 24
33989911 10.1016/j.ejmech.2021.113408 Plasmodium falciparum 23
20547801 10.1128/aac.00183-10 Plasmodium falciparum 23
37043698 10.1021/acs.jnatprod.2c01155 Huh-7 23
37043698 10.1021/acs.jnatprod.2c01155 Hep 3B2 23
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
8450319 10.1021/np50091a005 Unchecked 22
37556947 10.1016/j.ejmech.2023.115694 Plasmodium falciparum 21
37130472 10.1016/j.ejmech.2023.115400 ADMET 21
30408747 10.1016/j.ejmech.2018.10.061 ADMET 21
29420891 10.1021/acs.jmedchem.7b01417 Mus musculus 20
28800458 10.1016/j.ejmech.2017.07.061 Plasmodium falciparum 18
23837878 10.1021/jm400656s Plasmodium falciparum 18
28635296 10.1021/acs.jmedchem.7b00621 Plasmodium falciparum 16
29754074 10.1016/j.ejmech.2018.04.038 Plasmodium falciparum 16
17404003 10.1128/aac.01479-06 Plasmodium falciparum 16

Data from ChEMBL 36 via Core Engine