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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

chloroquine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key WHTVZRBIWZFKQO-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Chloroquine was first described in 1934, emerging from a search for synthetic antimalarial compounds that were superior to quinine. From the mid-1940s, chloroquine use became widespread as both a highly effective treatment for all forms of malaria and as a prophylactic agent. The emergence of strains of P. falciparum resistant to the drug was first reported in 1957 and has continued to spread. Chloroquine is still a useful medicine for prevention and treatment in malaria regions where P. falciparum is not endemic because P. vivax, P. malariae and P. ovale are sensitive to chloroquine in most of the regions where they occur.