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
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Summary of Clinical Use Click here for help
Piperaquine is approved by the EMA for use in the treatment of malaria, only as part of an ACT with artenimol (trade name Eurartesim®). The FDA granted Orphan Drug designation for Eurartesim® in 2007 for the treatment of uncomplicated malaria (link to FDA Orphan Drug Approval record here).
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