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.
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 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
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
The FDA has approved, under Priority Review, single-dose tafenoquine for the radical cure of P. vivax malaria in adults. The compound is not indicated for the treatment of acute P. vivax infection and should be coadministered with an appropriate antimalarial partner. Tafenoquine had previously been granted a Breakthrough Therapy designation by the FDA (December 2013), followed in November 2017 by the submission of a New Drug Application (NDA). The approval was based on efficacy and safety data from a number of clinical trials including the randomised, double-blind, Phase 2b/3 studies: DETECTIVE (NCT01376167 [2-3]) and GATHER (NCT02216123 [4]). Click here to link to ClinicalTrials.gov's complete list of tafenoquine trials. In August 2018, the FDA expanded tafenoquine's approval status to allow use of Arakoda® tablets as a once weekly prophylactic for the prevention of malaria infection in people aged 18 years and older.
Testing for glucose-6-phosphate dehydrogenase (G6PD) deficiency is required before administration because tafenoquine, like primaquine, causes haemolysis in genetically sensitive individuals [5].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01376167 Ph 2B/3 Tafenoquine (TFQ) Study in Prevention of Vivax Relapse Phase 2 Interventional GlaxoSmithKline
NCT02216123 Study to Assess the Incidence of Hemolysis, Safety, and Efficacy of Tafenoquine (SB-252263, WR238605) Versus Primaquine in Subjects With Plasmodium Vivax Malaria Phase 3 Interventional GlaxoSmithKline
Pharmacokinetics Click here for help
The terminal half-life of elimination of tafenoquine is 14 days [1].
External links Click here for help