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)
1. Combrinck JM, Mabotha TE, Ncokazi KK, Ambele MA, Taylor D, Smith PJ, Hoppe HC, Egan TJ. (2013)
Insights into the role of heme in the mechanism of action of antimalarials.
ACS Chem Biol, 8 (1): 133-7. [PMID:23043646]
2. De D, Krogstad FM, Byers LD, Krogstad DJ. (1998)
Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines.
J Med Chem, 41 (25): 4918-26. [PMID:9836608]
3. De D, Krogstad FM, Cogswell FB, Krogstad DJ. (1996)
Aminoquinolines that circumvent resistance in Plasmodium falciparum in vitro.
Am J Trop Med Hyg, 55 (6): 579-83. [PMID:9025680]
4. Delves M, Plouffe D, Scheurer C, Meister S, Wittlin S, Winzeler EA, Sinden RE, Leroy D. (2012)
The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.
PLoS Med, 9 (2): e1001169. [PMID:22363211]
5. Hocart SJ, Liu H, Deng H, De D, Krogstad FM, Krogstad DJ. (2011)
4-aminoquinolines active against chloroquine-resistant Plasmodium falciparum: basis of antiparasite activity and quantitative structure-activity relationship analyses.
Antimicrob Agents Chemother, 55 (5): 2233-44. [PMID:21383099]
6. Koita OA, Sangaré L, Miller HD, Sissako A, Coulibaly M, Thompson TA, Fongoro S, Diarra Y, Ba M, Maiga A et al.. (2017)
AQ-13, an investigational antimalarial, versus artemether plus lumefantrine for the treatment of uncomplicated Plasmodium falciparum malaria: a randomised, phase 2, non-inferiority clinical trial.
Lancet Infect Dis, 17 (12): 1266-1275. [PMID:28916443]
7. Ridley RG, Hofheinz W, Matile H, Jaquet C, Dorn A, Masciadri R, Jolidon S, Richter WF, Guenzi A, Girometta MA et al.. (1996)
4-aminoquinoline analogs of chloroquine with shortened side chains retain activity against chloroquine-resistant Plasmodium falciparum.
Antimicrob Agents Chemother, 40 (8): 1846-54. [PMID:8843292]