tafenoquine

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 5.3
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2018))
IUPAC Name
N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
International Nonproprietary Names
INN number INN
7835 tafenoquine
Synonyms
Arakoda® | Krintafel® | WR238605
Comments
Tafenoquine is an 8-aminoquinoline derivative that has potent antimalarial activity and is a synthetic analogue of primaquine.
The INN record for tafenoquine indicates that it 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.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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