tafenoquine   Click here for help

GtoPdb Ligand ID: 9722

Synonyms: Arakoda® | etaquine | Krintafel® | WR238605
Approved drug Antimalarial Ligand
tafenoquine is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: 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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES NCCCC(Nc1cc(OC)c(c2c1nc(OC)cc2C)Oc1cccc(c1)C(F)(F)F)C
Isomeric SMILES NCCCC(Nc1cc(OC)c(c2c1nc(OC)cc2C)Oc1cccc(c1)C(F)(F)F)C
InChI InChI=1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3
InChI Key LBHLFPGPEGDCJG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2018))
IUPAC Name Click here for help
N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
International Nonproprietary Names Click here for help
INN number INN
7835 tafenoquine
Synonyms Click here for help
Arakoda® | etaquine | Krintafel® | WR238605
Database Links Click here for help
CAS Registry No. 106635-80-7 (source: Scifinder)
ChEMBL Ligand CHEMBL298470
DrugCentral Ligand 3578
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
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Search UniChem for chemical match using the InChIKey LBHLFPGPEGDCJG-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone LBHLFPGPEGDCJG
Wikipedia Tafenoquine