CHLOROQUINE PHOSPHATE

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Trade Names
Synonyms
Status
Molecule Category Salt-form
UNII 6E17K3343P
EPA CompTox DTXSID7044681
Parent Compound: CHLOROQUINE

Structure

InChI Key QKICWELGRMTQCR-UHFFFAOYSA-N
Smiles CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=P(O)(O)O.O=P(O)(O)O
InChI
InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H32ClN3O8P2
Molecular Weight 515.87
AlogP 4.81
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 28.16
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Ferriprotoporphyrin IX inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 20
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 7
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M27 family
- - - - 7-7
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 84
Assay Description Organism Bioactivity Reference
In vitro inhibitory activity against chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum 180.0 nM
In vitro inhibitory activity against chloroquine-sensitive Plasmodium falciparum K1 Plasmodium falciparum 23.0 nM
In vitro antimalarial activity against multidrug-resistant Plasmodium falciparum K1 Plasmodium falciparum 0.16 ug.mL-1
In vitro growth inhibition as IC50 against chloroquine-resistant Plasmodium falciparum FcB1 Plasmodium falciparum 47.0 nM
In vitro growth inhibition as IC50 against chloroquine-resistant Plasmodium falciparum FcB2 Plasmodium falciparum 110.0 nM
In vitro inhibition as IC50 against Plasmodium falciparum by [3H]hypoxanthine uptake Plasmodium falciparum 160.0 ug.mL-1
In vitro inhibitory activity against Plasmodium berghei Plasmodium berghei 72.0 nM
In vitro inhibitory activity against Plasmodium falciparum FcB1 Plasmodium falciparum 47.0 nM
In vitro inhibitory activity against Plasmodium falciparum FCB2 Plasmodium falciparum 104.5 nM
In vitro antiplasmodial concentration against multidrug-resistant Plasmodium falciparum K1 Plasmodium falciparum K1 180.0 nM
In vitro antiplasmodial activity for Plasmodium falciparum Plasmodium falciparum 246.0 nM
In vitro inhibition of Plasmodium falciparum K1 Plasmodium falciparum 91.0 nM
In vitro inhibition of Plasmodium falciparum W2 Plasmodium falciparum 70.0 nM
In vitro inhibition of Plasmodium falciparum F32 Plasmodium falciparum 10.0 nM
In vitro inhibition of Plasmodium falciparum FcB1 Plasmodium falciparum 50.0 nM
Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by SYBR green assay Plasmodium falciparum 8.1 nM
Growth inhibition after 72 hrs of Plasmodium falciparum 3D7 by HRPII ELISA Plasmodium falciparum 7.5 nM
Growth inhibition after 72 hrs of Plasmodium falciparum D6 by SYBR green I assay Plasmodium falciparum 6.1 nM
Growth inhibition after 72 hrs of Plasmodium falciparum D6 by HRPII ELISA Plasmodium falciparum 5.9 nM
Growth inhibition after 72 hrs of Plasmodium falciparum W2 by SYBR green I assay Plasmodium falciparum 35.1 nM
Growth inhibition after 72 hrs of Plasmodium falciparum W2 by HRPII ELISA Plasmodium falciparum 33.2 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 infected human erythrocytes assessed by [3H]hypoxanthine uptake Plasmodium falciparum K1 0.21 ug.mL-1
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D10 by LDH assay Plasmodium falciparum 16.5 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 by LDH assay Plasmodium falciparum 293.5 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum NF54 by [3H]hypoxanthine uptake Plasmodium falciparum 4.7 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 by [3H]hypoxanthine uptake Plasmodium falciparum 48.5 nM
Cytotoxicity against human K562 cells by MTT assay Homo sapiens 31.83 nM
Inhibition of CYP2D6 at 3 uM None 20.4 %
Inhibition of CYP3A4 at 3 uM None 6.8 %
Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 Plasmodium falciparum K1 310.0 nM
Cytotoxicity against human KB cells by microplate method Homo sapiens 600.0 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by [3H]hypoxanthine uptake Plasmodium falciparum K1 0.16 ug.mL-1
Antiplasmodial activity after 24 hrs against chloroquine-sensitive Plasmodium falciparum Nigerian by [3H]hypoxanthine uptake Plasmodium falciparum 70.0 nM
Antiplasmodial activity after 72 hrs against chloroquine-sensitive Plasmodium falciparum Nigerian by [3H]hypoxanthine uptake Plasmodium falciparum 60.0 nM
Antiplasmodial activity after 24 hrs against chloroquine-resistant Plasmodium falciparum FcM29 by [3H]hypoxanthine uptake Plasmodium falciparum 450.0 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum FcM29 after 72 hrs by [3H]hypoxanthine uptake Plasmodium falciparum 420.0 nM
Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum HB3 after 48 hrs by LDH reporter activity Plasmodium falciparum HB3 28.0 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1 after 48 hrs by LDH activity Plasmodium falciparum K1 630.0 nM
Antimalarial activity after 48 hrs against chloroquine-sensitive Plasmodium falciparum T9-96 by LDH reporter assay Plasmodium falciparum 228.0 nM
Antimalarial activity after 48 hrs against chloroquine-resistant Plasmodium falciparum K1 by LDH reporter assay Plasmodium falciparum K1 51.0 nM
Antiplasmodial activity against multi drug-resistant Plasmodium falciparum K1 in erythrocytes by [3H]hypoxanthine uptake Plasmodium falciparum K1 200.0 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by [3H]hypoxanthine uptake Plasmodium falciparum K1 0.16 ug.mL-1
Antiplasmodial activity after 36 hrs against chloroquine-sensitive Plasmodium falciparum FCA 20 in human erythrocytes by [3H]hypoxanthine uptake Plasmodium falciparum 0.01 ug.mL-1
Antiplasmodial activity after 36 hrs against chloroquine-resistant Plasmodium falciparum W2 in human erythrocytes by [3H]hypoxanthine uptake Plasmodium falciparum 0.148 ug.mL-1
Antimalarial activity against Plasmodium falciparum 3D7A infected erythrocytes by [3H]hypoxanthine uptake Plasmodium falciparum 31.0 nM
Antimalarial activity against Plasmodium falciparum FCR3-A infected erythrocytes as [3H]hypoxanthine incorporation Plasmodium falciparum 300.0 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 Plasmodium falciparum 48.0 nM
Antimalarial activity against Plasmodium falciparum K1 by [3H]hypoxanthine uptake Plasmodium falciparum K1 310.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 9.1 nM
Antimalarial activity against Plasmodium falciparum K1 Plasmodium falciparum K1 890.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 assessed as growth inhibition by [3H]hypoxanthine incorporation assay Plasmodium falciparum 29.6 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 (Thailand) assessed as growth inhibition by [3H]hypoxanthine incorporation assay Plasmodium falciparum K1 150.2 nM
Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum MRC-02 infected in human erythrocyte assessed as inhibition of schizont maturation after 24 hrs Plasmodium falciparum 21.0 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum RKL09 infected in human erythrocyte assessed as inhibition of schizont maturation after 24 hrs Plasmodium falciparum 177.0 nM
Antiplasmodial activity in chloroquine-sensitive Plasmodium berghei ANKA infected BALB/c mice (Mus musculus) assessed as inhibition of parasitemia at 10 mg/kg, intraperitoneally daily once for 4 days Plasmodium berghei 100.0 %
Antiplasmodial activity in chloroquine-nonsensitive Plasmodium yoelii infected BALB/c mice (Mus musculus) assessed as inhibition of parasitaemia at 10 mg/kg, intraperitoneally daily once for 4 days Plasmodium yoelii 98.1 %
Antiplasmodial activity in chloroquine-nonsensitive Plasmodium yoelii infected BALB/c mice (Mus musculus) assessed as inhibition of parasitaemia at 3 mg/kg, intraperitoneally daily once for 4 days Plasmodium yoelii 32.7 %
Antiplasmodial activity in chloroquine-nonsensitive Plasmodium yoelii infected BALB/c mice (Mus musculus) assessed as inhibition of parasitaemia at 1 mg/kg, intraperitoneally daily once for 4 days Plasmodium yoelii 32.7 %
Antiplasmodial activity in chloroquine-nonsensitive Plasmodium yoelii infected intraperitoneally dosed BALB/c mice (Mus musculus) assessed as inhibition of parasitaemia administered daily once for 4 days Plasmodium yoelii 1.31 % Antiplasmodial activity in chloroquine-nonsensitive Plasmodium yoelii infected intraperitoneally dosed BALB/c mice (Mus musculus) assessed as inhibition of parasitaemia administered daily once for 4 days Plasmodium yoelii 2.96 %
Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum MRC2 infected in human erythrocytes after 24 hrs by Giemsa staining Plasmodium falciparum 24.0 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum RKL9 after 24 hrs by Giemsa staining Plasmodium falciparum 38.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium berghei ANKA infected in Swiss mice (Mus musculus) assessed as suppression of parasitaemia at 5 mg/kg, perorally for 4 days measured on day 5 relative to control Plasmodium berghei str. ANKA 96.82 %
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in human erythrocyte after 48 h by SYBR-Green-1 assay Plasmodium falciparum 0.02063 ug.mL-1
Antimalarial activity against chloroquine-resistant Plasmodium falciparum RKL9 infected in human erythrocyte after 48 h by SYBR-Green-1 assay Plasmodium falciparum 0.2064 ug.mL-1
Inhibition of beta-hematin formation after 18 hrs by microtiter plate assay None 1.3 ug.mL-1
Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 125.89 nM
Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR green assay Plasmodium falciparum D10 316.23 nM
Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 316.23 nM
Antiplasmodial activity against Plasmodium falciparum harboring K1 allele group of msp1, 3D7 allele group of msp2 gene and 94 bp of 7A11, 196bp of C4M79 and 336bp of C4M69 locus measured on day 23 by [3H]hypoxanthine incorporation assay Plasmodium falciparum 62.0 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by firefly luciferase reporter gene assay Plasmodium falciparum 30.0 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum TM90C2B after 72 hrs by MSF assay Plasmodium falciparum 307.38 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum TM90C2A after 72 hrs by MSF assay Plasmodium falciparum 249.84 nM
Antimalarial activity against multi drug resistant Plasmodium falciparum TM91C235 after 72 hrs by MSF assay Plasmodium falciparum 226.21 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 after 72 hrs by MSF assay Plasmodium falciparum 14.22 nM
Inhibition of Clostridium botulinum recombinant BoNT/A light chain at 20 mM by reverse-phase HPLC analysis Clostridium botulinum 7.0 %
Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hrs by MSF assay Plasmodium falciparum 634.3 nM
Antimalarial activity against Plasmodium falciparum NF54 infected in human serum after 48 hrs by fluorometric method Plasmodium falciparum 0.02 ug.mL-1
Antimalarial activity against Plasmodium falciparum NF54 infected in human serum at 22.2 ug/ml after 48 hrs by fluorometric method Plasmodium falciparum 68.4 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 84.34 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 99.18 %
Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay Homo sapiens 2.0 ug.mL-1
Antimalarial activity against liver stage Plasmodium berghei ANKA sporozoites infected in human HepG2 cells after 48 hrs by luciferase reporter gene assay Plasmodium berghei 2.0 ug.mL-1
Antimalarial activity against drug-resistant Plasmodium falciparum C235 after 72 hrs by SYBR green I staining-based fluorescence assay Plasmodium falciparum 0.0966 ug.mL-1
Antimalarial activity against drug-sensitive Plasmodium falciparum D6 after 72 hrs by SYBR green I staining-based fluorescence assay Plasmodium falciparum D6 0.0082 ug.mL-1
Antiplasmodial activity against chloroquine-resistant asexual erythrocytic stage of Plasmodium falciparum Dd2 assessed as parasite growth inhibition by lactate dehydrogenase assay Plasmodium falciparum Dd2 140.0 nM
Antiplasmodial activity against chloroquine-sensitive asexual erythrocytic stage of Plasmodium falciparum D10 assessed as parasite growth inhibition by lactate dehydrogenase assay Plasmodium falciparum D10 21.8 nM
Antiplasmodial activity against asexual erythrocytic stage of chloroquine-resistant Plasmodium falciparum Dd2 assessed as parasite growth inhibition after 48 hrs by lactate dehydrogenase assay Plasmodium falciparum Dd2 300.0 nM
Antiplasmodial activity against asexual erythrocytic stage of chloroquine-sensitive Plasmodium falciparum NF54 assessed as parasite growth inhibition after 48 hrs by lactate dehydrogenase assay Plasmodium falciparum NF54 13.8 nM
Inhibition of Clostridium botulinum recombinant BoNT/A light chain using N-terminal acetylated, C-terminal aminated SNAP-25 (187-203) as substrate at 20 uM by reverse-phase HPLC analysis Clostridium botulinum 6.51 %
Antiplasmodial activity against multi-drug resistant Plasmodium falciparum K1 in human erythrocytes assessed as growth inhibition after 48 hrs by optical microscopy Plasmodium falciparum K1 330.0 nM
Antiplasmodial activity against drug susceptible Plasmodium falciparum 3D7 NF54 isolate in human erythrocytes assessed as growth inhibition after 48 hrs by optical microscopy Plasmodium falciparum 3D7 110.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in human erythrocyte assessed as parasite viability after 48 hrs by [3H]hypoxanthine incorporation based liquid scintillation counting analysis Plasmodium falciparum 3D7 0.034 ug.mL-1 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in human erythrocyte assessed as parasite viability after 48 hrs by [3H]hypoxanthine incorporation based liquid scintillation counting analysis Plasmodium falciparum 3D7 66.0 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum indochina W2 assessed as [3H]-hypoxanthine incorporation by liquid scintillation counting analysis Plasmodium falciparum 5.0 nM
Antimalarial activity against chloroquine-susceptible Plasmodium falciparum african D6 assessed as [3H]-hypoxanthine incorporation by liquid scintillation counting analysis Plasmodium falciparum D6 6.0 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum thailand TM91C235 assessed as [3H]-hypoxanthine incorporation by liquid scintillation counting analysis Plasmodium falciparum 5.0 nM
Binding affinity to heme assessed as inhibition of beta-hematin formation by BHIA assay relative to hemin None 6.0 equiv
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum RKL9 infected in human RBC assessed as effect on schizont maturation after 24 hrs by Geimsa staining-based assay Plasmodium falciparum 192.0 nM
Antimalarial activity against chloroquine-sensitive NF54 isolated Plasmodium falciparum 3D7 infected in erythrocytes assessed as inhibition of parasitic growth after 48 hrs by optical microscopy Plasmodium falciparum 180.0 nM
Antiplasmodial activity against chloroquine sensitive Plasmodium falciparum 3D7 infected in human erythrocytes incubated for 72 hrs by SYBR Green1-based fluorescence analysis Plasmodium falciparum 3D7 11.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 after 72 hrs by SYBR Green-1 staining based fluorescence assay Plasmodium falciparum 3D7 5.4 nM
Antiplasmodial activity against chloroquine-sensitive synchronized trophozoite stage of Plasmodium falciparum NF54 after 48 hrs by NBT dye based LDH assay Plasmodium falciparum NF54 8.3 nM
Antiplasmodial activity against chloroquine-resistant synchronized trophozoite stage of Plasmodium falciparum Dd2 after 48 hrs by NBT dye based LDH assay Plasmodium falciparum Dd2 226.4 nM
Antiplasmodial activity against chloroquine-resistant synchronized trophozoite stage of Plasmodium falciparum 7G8 after 48 hrs by NBT dye based LDH assay Plasmodium falciparum 7G8 150.3 nM
Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 assessed as reduction in parasitic LDH activity after 48 hrs by Malstat reagent based spectrofluorometric method Plasmodium falciparum 3D7 18.9 ug.mL-1
Antiparasitic activity against chloroquine-resistant Plasmodium falciparum FcB1/Columbia infected in human erythrocytes assessed as reduction in [3H]-hypoxanthine incorporation incubated for 24 hrs assay by liquid scintillation spectrometry Plasmodium falciparum FcB1/Columbia 50.0 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infecetd in RBC after 72 hrs by SYBR Green dye-based fluorescence assay Plasmodium falciparum 3D7 8.8 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 infecetd in RBC after 72 hrs by SYBR Green dye-based fluorescence assay Plasmodium falciparum K1 560.0 nM
Antiplasmodial activity against Plasmodium berghei ANKA infected in mouse assessed as inhibition of parasitemia at 3 mg/kg/day, po for 4 consecutive days starting from 2 hrs post infection by MSF assay relative to control Plasmodium berghei ANKA 88.5 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 5.84 %
Anti-plasmodial activity against chloroquine resistant Plasmodium falciparum RKL9 infected in human erythrocytes after 24 hrs by Giemsa staining-based method Plasmodium falciparum 193.0 nM
Antimalarial activity against artemisinin-resistant Plasmodium falciparum MRA1240 pretreated for 24 hrs followed by [3H]-hypoxanthine addition and measured after 24 hrs by [3H]-hypoxanthine growth inhibition assay Plasmodium falciparum 97.0 nM
Antimalarial activity against Plasmodium falciparum D6 pretreated for 24 hrs followed by [3H]-hypoxanthine addition and measured after 24 hrs by [3H]-hypoxanthine growth inhibition assay Plasmodium falciparum 16.0 nM
Antimalarial activity against Plasmodium falciparum W2 pretreated for 24 hrs followed by [3H]-hypoxanthine addition and measured after 24 hrs by [3H]-hypoxanthine growth inhibition assay Plasmodium falciparum 150.0 nM
Antimalarial activity against artemisinin-sensitive Plasmodium falciparum MRA1239 pretreated for 24 hrs followed by [3H]-hypoxanthine addition and measured after 24 hrs by [3H]-hypoxanthine growth inhibition assay Plasmodium falciparum 75.7 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.58 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.08 %
Antimalarial activity against Plasmodium yoelii BY265RFP infected in Kunming mouse assessed as inhibition of parasitemia at 10 mg/kg/day, ig administered for 4 days starting from 3 hrs post infection and measured at 4 days post infection by Wright-Giemsa staining based microscopic assay relative to control Plasmodium yoelii 97.9 %
Antimalarial activity against chloroquine resistant Plasmodium falciparum RKL9 assessed as reduction in schizont maturation incubated for 24 hrs by Giemsa staining based assay Plasmodium falciparum 188.0 nM

Cross References

Resources Reference
ChEBI 3638
ChEMBL CHEMBL58510
FDA SRS 6E17K3343P
Guide to Pharmacology 5535
KEGG C07625
PDB CLQ
PubChem 64927
SureChEMBL SCHEMBL40827
ZINC ZINC01530861
CONTENTS