Ligand id: 9722

Name: tafenoquine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 78.63
Molecular weight 463.21
XLogP 5.51
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2018))
International Nonproprietary Names
INN number INN
7835 tafenoquine
Arakoda® | Krintafel® | WR238605
Tafenoquine is an 8-aminoquinoline and a synthetic analogue of primaquine. Tafenoquine has a significantly longer elimination half-life as compared to primaquine and is the first drug to be approved for single-dose treatment of relapsing P. vivax malaria. The compound was awarded MMV Project of the Year (2013).
The INN record for tafenoquine indicates that this is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem and ChEMBL entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 76969187 and PubChem CID 76969188.

Potential Target/Mechanism Of Action: As the precise mechanism of action of tafenoquine is not yet known, we do not have a molecular target for this compound.
Database Links
CAS Registry No. 106635-80-7 (source: Scifinder)
ChEMBL Ligand CHEMBL298470
GtoPdb PubChem SID 374883823
PubChem CID 115358
Search Google for chemical match using the InChIKey LBHLFPGPEGDCJG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LBHLFPGPEGDCJG
Search PubMed clinical trials tafenoquine
Search PubMed titles tafenoquine
Search PubMed titles/abstracts tafenoquine
Search UniChem for chemical match using the InChIKey LBHLFPGPEGDCJG-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone LBHLFPGPEGDCJG
Wikipedia Tafenoquine