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
SMILES / InChI / InChIKey
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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
InChI Key UCRHFBCYFMIWHC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (EMA (2011) in combination with artenimol)
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
Database Links Click here for help
ChEMBL Ligand CHEMBL303933
DrugBank Ligand DB13941
DrugCentral Ligand 4193
GtoPdb PubChem SID 375973214
PubChem CID 122262
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