Tafenoquine Chemical Properties

Melting point:

60 - 63°C

Boiling point:

565.6±50.0 °C(Predicted)

Density 

1.237±0.06 g/cm3(Predicted)

storage temp. 

4°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.36±0.10(Predicted)

form 

Solid

color 

Dark Orange to Very Dark Orange

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

InChIKey

LBHLFPGPEGDCJG-UHFFFAOYSA-N

SMILES

C(N)CCC(NC1=C2C(=C(OC3=CC=CC(C(F)(F)F)=C3)C(OC)=C1)C(C)=CC(OC)=N2)C

Tafenoquine Usage And Synthesis

Uses

Tafenoquine is a pharmaceutical developed for the treatment of Plasmodium vivax malaria. Tafenoquine is also being explored for pharmaceutical use for inhibition of Toxoplasma gondii growth.

Definition

ChEBI: N(4)-{2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl}pentane-1,4-diamine is an aminoquinoline that is 8-aminoquinoline which is substituted by methoxy groups at positions 2 and 6, a methyl group at position 4, and a m-(trifluoromethyl)phenoxy group at position 5, and in which the amino substituent at position 8 is itself substituted by a 5-aminopentan-2-yl group. It is a member of (trifluoromethyl)benzenes, an aminoquinoline, an aromatic ether, a primary amino compound and a secondary amino compound.

Pharmaceutical Applications

Etaquine. A synthetic 8-aminoquinoline, formulated as the succinate for oral administration. Tafenoquine is an effective schizonticide against P. falciparum and P. vivax. It is also active against the pre-erythrocytic stages of these species and the hypnozoites of P. vivax. A dosage of 100 mg base corresponds to 125 mg salt. Oral absorption is slow with a maximum plasma concentration reached after 12 h. The half-life is 2 weeks, significantly longer than that of primaquine. It is not eliminated via the kidneys. Toxicity and side effects are similar to those of primaquine. Development of methemoglobinemia is common. Patients with G6PD deficiency may develop severe hemolysis.
It is in clinical development for the treatment and prophylaxis of P. vivax malaria and for the treatment of P. falciparum infection.

in vivo