Structure via PubChem · Public domain (PubChem)
piperaquine
Sign in to saveAlso known as piperaquinoline, 1,3-bis[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propane
Piperaquine is an antiparasitic drug used in combination with dihydroartemisinin to treat malaria. Piperaquine was developed under the Chinese National Malaria Elimination Programme in the 1960s and was adopted throughout China as a replacement for the structurally similar antimalarial drug chloroquine. Due to widespread parasite resistance to piperaquine, the drug fell out of use as a monotherapy, and is instead used as a partner drug for artemisinin combination therapy. Piperaquine kills parasites by disrupting the detoxification of host heme.
Chemical data
- Formula
- C29H32Cl2N6
- Molecular weight
- 535.5 g/mol
- IUPAC name
- 7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
- SMILES
- C1CN(CCN1CCCN2CCN(CC2)C3=C4C=CC(=CC4=NC=C3)Cl)C5=C6C=CC(=CC6=NC=C5)Cl
- InChIKey
- UCRHFBCYFMIWHC-UHFFFAOYSA-N
- XLogP
- 5.6
- Polar surface area
- 38.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- malaria, Plasmodium falciparum malaria, Plasmodium vivax malaria, Fever
via ChEMBL · EBI
Research
1,253 papers- The plasmepsin-piperaquine paradox persists in Plasmodium falciparum.PLoS pathogens · 2025
- Therapeutic efficacy of dihydroartemisinin-piperaquine combination for the treatment of uncomplicated malaria in Ghana.Frontiers in cellular and infection microbiology · 2022
- A Comprehensive Review on the Pharmacokinetics and Bioanalysis of Piperaquine.Current drug metabolism · 2025
- Piperaquine: a resurgent antimalarial drug.Drugs · 2005
- Dihydroartemisinin/Piperaquine: a review of its use in the treatment of uncomplicated Plasmodium falciparum malaria.Drugs · 2012
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 534.207
Show 3 more facts
- chemical formula
- C₂₉H₃₂Cl₂N₆
- canonical SMILES
- C1CN(CCN1CCCN2CCN(CC2)C3=C4C=CC(=CC4=NC=C3)Cl)C5=C6C=CC(=CC6=NC=C5)Cl
- subject has role
- antimalarial
via Wikidata · CC0
~4 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Contraindications
- Pharmacology
- Mechanism of action
- Resistance
- Pharmacokinetics
- Chemistry
- History
- References
Piperaquine is an antiparasitic drug used in combination with dihydroartemisinin to treat malaria. Piperaquine was developed under the Chinese National Malaria Elimination Programme in the 1960s and was adopted throughout China as a replacement for the structurally similar antimalarial drug chloroquine. Due to widespread parasite resistance to piperaquine, the drug fell out of use as a monotherapy, and is instead used as a partner drug for artemisinin combination therapy. Piperaquine kills parasites by disrupting the detoxification of host heme.
==Medical uses== Piperaquine is used in combination with dihydroartemisinin for the treatment of malaria. This combination is one of several artemisinin combination therapies recommended by the World Health Organization for treatment of uncomplicated malaria. This combination is also recommended by the World Health Organization for treatment of severe malaria after administration of artesunate.
Excerpted from Wikipedia’s “piperaquine” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0