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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(NC(C)CCCN)C=C(OC)C(OC3=CC=CC(=C3)C(F)(F)F)=C2C(C)=C1

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
Stereochemistry RACEMIC
Additional Stereochemistry
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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARAKODA
PubMed

PubMed

TitleDatePubMed
8-aminoquinolines effective against Pneumocystis carinii in vitro and in vivo.
1993 Oct
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995 Nov 24
Malaria chemoprophylaxis in the age of drug resistance. I. Currently recommended drug regimens.
2001 Jul 15
Structural modifications of quinoline-based antimalarial agents: Recent developments.
2010 Apr
Antileishmanial and antitrypanosomal activities of the 8-aminoquinoline tafenoquine.
2010 Dec
Anti-malarial drugs and the prevention of malaria in the population of malaria endemic areas.
2010 Dec 13
Establishment of an in vitro assay for assessing the effects of drugs on the liver stages of Plasmodium vivax malaria.
2010 Dec 9
Efficacy and safety of chloroquine for treatment in patients with uncomplicated Plasmodium vivax infections in endemic countries.
2010 Nov
Operational strategies to achieve and maintain malaria elimination.
2010 Nov 6
Anti-bacterial activity of intermittent preventive treatment of malaria in pregnancy: comparative in vitro study of sulphadoxine-pyrimethamine, mefloquine, and azithromycin.
2010 Oct 29
A SYBR Green 1-based in vitro test of susceptibility of Ghanaian Plasmodium falciparum clinical isolates to a panel of anti-malarial drugs.
2013 Dec 17
Patents

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
Created
by admin
on Tue Mar 06 17:08:31 UTC 2018
Edited
by admin
on Tue Mar 06 17:08:31 UTC 2018
Record UNII
262P8GS9L9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAFENOQUINE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
TAFENOQUINE [MI]
Common Name English
SB-252263-AAB
Code English
TAFENOQUINE [WHO-DD]
Common Name English
TAFENOQUINE [INN]
Common Name English
TAFENOQUINE [MART.]
Common Name English
TAFENOQUINE [USAN]
Common Name English
Code System Code Type Description
MERCK INDEX
M10429
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY Merck Index
CAS
106635-80-7
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
EVMPD
SUB04666MIG
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
NCI_THESAURUS
C73006
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
PUBCHEM
115358
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY SWITZERF
MESH
C055852
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
ChEMBL
CHEMBL298470
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
INN
7835
Created by admin on Tue Mar 06 17:08:31 UTC 2018 , Edited by admin on Tue Mar 06 17:08:31 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY