chloroquine   

GtoPdb Ligand ID: 5535

Synonyms: Aralen® | chloraquine | Malaquin®
chloroquine is an approved drug (FDA (1949), UK (2000))
Compound class: Synthetic organic
Comment: Chloroquine is a 4-aminoquinoline and used primarily as an antimalarial drug.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 444810 and PubChem CID 639540. The PDB entry listed in the links table is for (R)-chloroquine.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 28.16
Molecular weight 319.18
XLogP 4.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
Isomeric SMILES CCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
InChI InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChI Key WHTVZRBIWZFKQO-UHFFFAOYSA-N
Bioactivity Comments
Chloroquine is active against only the erythrocytic forms of P. vivax, P. malariae, and susceptible strains of P. falciparum (but not the gametocytes of P. falciparum).
In humans, chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3).
Selectivity at GPCRs
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MRGPRX1 Hs Agonist Agonist 3.5 pEC50 - 2
pEC50 3.5 (EC50 2.97x10-4 M) [2]
Whole organism assay data
Key to terms and symbols Click on species/strain names for details Click column headers to sort
MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA PfD6 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 8.8x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite growth inhibition assay - - 7.9 pIC50 - 1
pIC50 7.9 (IC50 1.12x10-8 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf7G8 Parasite growth inhibition assay - - 7.2 pIC50 - 1
pIC50 7.2 (IC50 7.03x10-8 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfTM90C2A Parasite growth inhibition assay - - 7.0 pIC50 - 1
pIC50 7.0 (IC50 1.058x10-7 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1 Parasite growth inhibition assay - - 6.7 pIC50 - 1
pIC50 6.7 (IC50 1.98x10-7 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Parasite growth inhibition assay - - 6.6 pIC50 - 1
pIC50 6.6 (IC50 2.683x10-7 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfV1/S Parasite growth inhibition assay - - 6.5 pIC50 - 1
pIC50 6.5 (IC50 3.04x10-7 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)