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Details

Stereochemistry RACEMIC
Molecular Formula C24H28F3N3O3
Molecular Weight 463.4926
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAFENOQUINE

SMILES

COC1=NC2=C(C(C)=C1)C(OC3=CC=CC(=C3)C(F)(F)F)=C(OC)C=C2NC(C)CCCN

InChI

InChIKey=LBHLFPGPEGDCJG-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H28F3N3O3
Molecular Weight 463.4926
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Tafenoquine is anti-malaria drug originated in Walter reed army institute of research and developed by GSK and 60 Degrees Pharmaceuticals. In 2018 United States Food and Drug Administration (FDA) approved single dose tafenoquine for the radical cure (prevention of relapse) of Plasmodium vivax malaria. Tafenoquine, an 8-aminoquinoline antimalarial, is active against all the stages of Plasmodium species that include the hypnozoite (dormant stage) in the liver. Studies in vitro with the erythrocytic forms of Plasmodium falciparum suggest that tafenoquine may exert its effect by inhibiting hematin polymerization and inducing apoptotic like death of the parasite. In addition to its effect on the parasite, tafenoquine causes red blood cell shrinkage in vitro. Tafenoquine is active against pre-erythrocytic (liver) and erythrocytic (asexual) forms as well as gametocytes of Plasmodium species that include P. falciparum and P. vivax. The activity of tafenoquine against the pre-erythrocytic liver stages of the parasite, prevents the development of the erythrocytic forms of the parasite.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
217.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ARAKODA

Cmax

ValueDoseCo-administeredAnalytePopulation
147 ng/mL
200 mg single, oral
TAFENOQUINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
70 μg × h/mL
200 mg single, oral
TAFENOQUINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.5 day
200 mg single, oral
TAFENOQUINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
200 mg single, oral
TAFENOQUINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Loading regimen: 200 mg (2 of the 100 mg tablets) once daily for 3 days Maintenance regimen: 200 mg (2 of the 100 mg tablets) once weekly – start 7 days after the last loading regimen dose Terminal prophylaxis regimen: 200 mg (2 of the 100 mg tablets) one-time 7 days after the last maintenance dose
Route of Administration: Oral
In Vitro Use Guide
After 72 h of tafenoquine exposure, proliferation of L. donovani and Leishmania major promastigotes was inhibited at the micromolar range in a dose-dependent manner, with 50% effective concentrations (EC50s) of 5.6 ± 1.0 uM and 5.3 ± 2.1 uM for L. donovani.
Substance Class Chemical
Record UNII
262P8GS9L9
Record Status Validated (UNII)
Record Version