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Compound Detail

CHEMBL58510

CHLOROQUINE PHOSPHATE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=P(O)(O)O.O=P(O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL58510
Name CHLOROQUINE PHOSPHATE
Phase Approved
Structure Type MOL
InChI Key QKICWELGRMTQCR-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL76
Active Moiety CHEMBL76

Known Names

Aralen Arechin Avloclor Chloroquine diphosphate Chloroquine phosphate Chloroquini phosphas Malaquin Malarivon NSC-14050 Resochin SN-7618 WR-1522
14
Targets
116
Activities
3
Assay Types
0
PK Parameters
20
Publications
12
Known Names
8
Indications
1
Mechanisms

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

Extended Properties

Molecular Formula C18H32ClN3O8P2
MW 515.87
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.27

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ferriprotoporphyrin IX inhibitor INHIBITOR Ferriprotoporphyrin IX ✓ ✓

Indications

Malaria Arthritis, Rheumatoid Atrial Fibrillation HIV Infections Lupus Erythematosus, Systemic Pneumonia, Viral Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome

Activity Summary

IC50 112 meas. best 8.33
EC50 3 meas. best 8.08
Kd 1 meas. best 5.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.33 7.0875 4.7 97
Plasmodium falciparum
CHEMBL364
 EC50 8.08 7.295 8.3 2
K562
CHEMBL385
 IC50 7.5 7.5 31.8 1
Plasmodium berghei
CHEMBL612653
 IC50 7.14 7.14 72.0 1
Human coronavirus OC43
CHEMBL5209665
 EC50 6.51 6.51 306.0 1
KB
CHEMBL398
 IC50 6.22 6.22 600.0 1
Histone-lysine N-methyltransferase, H3 lysine-36 specific
CHEMBL3588738
 Kd 5.33 5.33 4700.0 1
MDA-MB-231
CHEMBL400
 IC50 4.65 4.65 22520.0 1
Unchecked
CHEMBL612545
 IC50 4.58 4.58 26100.0 1
MDA-MB-468
CHEMBL614335
 IC50 4.54 4.54 28580.0 1
HeLa
CHEMBL399
 IC50 4.52 4.52 30000.0 1
MCF7
CHEMBL387
 IC50 4.42 4.42 38440.0 1
HepG2
CHEMBL395
 IC50 4.42 4.42 37680.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 4.38 4.355 42030.0 2
184B5
CHEMBL4296396
 IC50 4.12 4.12 76130.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 4.7 nM 8.33 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum NF54 b... 18538567
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against multidrug-resistant Plasmodium falciparum thailand... 25801154
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against chloroquine-resistant Plasmodium falciparum indoch... 25801154
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 36931118
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against Plasmodium falciparum 3D7 assessed as parasite gro... 37556947
Plasmodium falciparum IC50 = 5.4 nM 8.27 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 af... 28159413
Plasmodium falciparum IC50 = 5.9 nM 8.23 Growth inhibition after 72 hrs of Plasmodium falciparum D6 by HRPII ELISA 17220424
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antimalarial activity against chloroquine-susceptible Plasmodium falciparum afri... 25801154
Plasmodium falciparum IC50 = 6.1 nM 8.21 Growth inhibition after 72 hrs of Plasmodium falciparum D6 by SYBR green I assay 17220424
Plasmodium falciparum IC50 = 7.5 nM 8.12 Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by HRPII ELISA 17220424
Plasmodium falciparum IC50 = 8.1 nM 8.09 Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by SYBR green assay 17220424
Plasmodium falciparum EC50 = 8.3 nM 8.08 Antimalarial activity against ring stage Plasmodium falciparum 3D7 infected in t... 30503412
Plasmodium falciparum IC50 = 8.3 nM 8.08 Antiplasmodial activity against chloroquine-sensitive synchronized trophozoite s... 29185748
Plasmodium falciparum IC50 = 8.8 nM 8.06 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 29216562
Plasmodium falciparum IC50 = 9.1 nM 8.04 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 19284751
Plasmodium falciparum IC50 = 10.0 nM 8.0 In vitro inhibition of Plasmodium falciparum F32 15456263
Plasmodium falciparum IC50 = 11.0 nM 7.96 Antiplasmodial activity against chloroquine sensitive Plasmodium falciparum 3D7 ... 26774925
Plasmodium falciparum IC50 = 13.8 nM 7.86 Antiplasmodial activity against asexual erythrocytic stage of chloroquine-sensit... 24602791
Plasmodium falciparum IC50 = 14.22 nM 7.85 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 aft... 23815186
Plasmodium falciparum IC50 = 14.0 nM 7.85 Antiplasmodial activity against CQ-sensitive Plasmodium falciparum NF54 at asexu... 37556947

Literature References

PubMed DOI Target Context # Activities
10201838 10.1016/s0960-894x(99)00057-8 Plasmodium falciparum 28
19506054 10.1128/aac.01509-08 Human coronavirus OC43 14
18538567 10.1016/j.bmcl.2008.05.042 Plasmodium berghei 13
17220424 10.1128/aac.01313-06 Plasmodium falciparum 12
23815186 10.1021/jm4006077 Plasmodium falciparum 10
30715882 10.1021/acs.jmedchem.8b01799 Plasmodium falciparum 8
15456263 10.1021/jm049792o Plasmodium falciparum 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
- 10.1101/2020.03.25.008482 SARS-CoV 7
20034790 10.1016/j.bmcl.2009.12.030 Plasmodium yoelii 5
19945197 10.1016/j.ejmech.2009.11.017 MDA-MB-231 5
19945197 10.1016/j.ejmech.2009.11.017 MDA-MB-468 5
25835356 10.1016/j.bmc.2015.03.029 Trypanosoma brucei brucei 5
19945197 10.1016/j.ejmech.2009.11.017 NON-PROTEIN TARGET 5
29185748 10.1021/acs.jmedchem.7b01537 Plasmodium falciparum 5
19945197 10.1016/j.ejmech.2009.11.017 MCF7 5
15801861 10.1021/jm040893w Plasmodium falciparum 4
18538567 10.1016/j.bmcl.2008.05.042 Plasmodium falciparum 4
17967541 10.1016/j.bmc.2007.10.031 Histidine-rich protein PFHRP-II 4
20576433 10.1016/j.bmcl.2010.05.069 Plasmodium falciparum 4

Data from ChEMBL 36 via Core Engine