piperaquine   Click here for help

GtoPdb Ligand ID: 10025

Approved drug Antimalarial Ligand
piperaquine is an approved drug (EMA (2011) in combination with artenimol)
Compound class: Synthetic organic
Comment: Piperaquine is a 4-aminoquinoline antimalarial compound.

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 6
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 38.74
Molecular weight 534.21
XLogP 5.59
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc2c(c1)nccc2N1CCN(CC1)CCCN1CCN(CC1)c1ccnc2c1ccc(c2)Cl
Isomeric SMILES Clc1ccc2c(c1)nccc2N1CCN(CC1)CCCN1CCN(CC1)c1ccnc2c1ccc(c2)Cl
InChI InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2
Guide to Malaria Pharmacology Comments
Piperaquine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019). Piperaquine is used in combination with artenimol as a curative treatment for malaria and is one of the artemisinin-based combination therapies (ACTs) recommended in the WHO Guidelines for the treatment of malaria [3].

Potential Target/Mechanism Of Action: As the precise MOA of piperaquine is not yet known, we do not have a molecular target for this compound. It is thought that piperaquine 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].