AQ-13   Click here for help

GtoPdb Ligand ID: 10391

Synonyms: Ro 47-0543
Antimalarial Ligand
Compound class: Synthetic organic
Comment: AQ-13 is a 4-aminoquinoline antimalarial compound related to chloroquine [3,7].

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 7
Topological polar surface area 28.16
Molecular weight 291.15
XLogP 3.45
No. Lipinski's rules broken 0
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Canonical SMILES CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
Isomeric SMILES CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
InChI InChI=1S/C16H22ClN3/c1-3-20(4-2)11-5-9-18-15-8-10-19-16-12-13(17)6-7-14(15)16/h6-8,10,12H,3-5,9,11H2,1-2H3,(H,18,19)
Guide to Malaria Pharmacology Comments
Despite the widespread emergence of P. falciparum strains that are resistant to chloroquine, the 4-aminoquinoline scaffold has continued to be the basis for the development of new antimalarial drug candidates. SAR studies have been undertaken to inform the development of aminoquinoline derivatives that are active against both chloroquine-susceptible and -resistant P. falciparum, with AQ-13 identified as a compound suitable for progression to clinical evaluation [2-3,5].

Potential Target/Mechanism Of Action: As the precise MOA of AQ-13 is not yet known, we do not have a molecular target for this compound. It is thought that AQ-13 has a similar MOA to chloroquine, killing the malaria parasite by causing a build up of toxic heme by inhibiting the enzyme that normally converts it to non-toxic haemozoin [1].