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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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 Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
Database Links Click here for help
ChEMBL Ligand CHEMBL303933
DrugBank Ligand DB13941
DrugCentral Ligand 4193
GtoPdb PubChem SID 375973214
PubChem CID 122262
Search Google for chemical match using the InChIKey UCRHFBCYFMIWHC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UCRHFBCYFMIWHC
UniChem Compound Search for chemical match using the InChIKey UCRHFBCYFMIWHC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UCRHFBCYFMIWHC-UHFFFAOYSA-N