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
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.