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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1949), UK (2000))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine
International Nonproprietary Names Click here for help
INN number INN
386 chloroquine
Synonyms Click here for help
Aralen® | chloraquine | Malaquin®
Database Links Click here for help
BitterDB Ligand 87
CAS Registry No. 54-05-7 (source: Scifinder)
ChEBI CHEBI:3638
ChEMBL Ligand CHEMBL76
DrugBank Ligand DB00608
DrugCentral Ligand 607
GtoPdb PubChem SID 178102177
Immunopaedia Search chloroquine
PubChem CID 2719
RCSB PDB Ligand CLQ
Search Google for chemical match using the InChIKey WHTVZRBIWZFKQO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WHTVZRBIWZFKQO
Search PubMed clinical trials chloroquine
Search PubMed titles chloroquine
Search PubMed titles/abstracts chloroquine
Search UniChem for chemical match using the InChIKey WHTVZRBIWZFKQO-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone WHTVZRBIWZFKQO
Wikipedia Chloroquine

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Tocris
Chloroquine diphosphate
Cat. No. 4109