chloroquine   Click here for help

GtoPdb Ligand ID: 5535

Synonyms: Aralen® | chloraquine | Malaquin®
Approved drug PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
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.
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2D Structure
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Physico-chemical Properties
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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
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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)
No information available.
Summary of Clinical Use Click here for help
Chloroquine is one of the antimalarials listed in the World Health Organization's Model List of Essential Medicines, with its recommended use restricted to the prevention and treatment of P. vivax infection in areas where resistance has not yet developed.
It is also used off-label for other conditions/diseases, including treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Chloroquine inhibits ferriprotoporphyrin IX (FP, a heme detoxifying enzyme) found in Plasmodium species. Chloroquine kills the malarial parasite by causing a build up of toxic heme by inhibiting the enzyme that normally converts it to non-toxic hamazion. Chloroquine may also form a complex with FP which is additionally highly toxic to the organism.
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