106635-80-7

Basic information

• Product Name: Tafenoquine
• Synonyms: Tafenoquine;4-[5-[3-(Trifluoromethyl)phenoxy]-2,6-dimethoxy-4-methyl-8-quinolinylamino]-1-pentanamine;8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinoline;N4-(2,6-diMethoxy-4-Methyl-5-(3-(trifluoroMethyl)phenoxy)quinolin-8-yl)pentane-1,4-diaMine;N4-{2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinyl}-1,4-pentanediamine
• CAS NO: 106635-80-7
• Molecular Formula: C₂₄H₂₈F₃N₃O₃
• Molecular Weight: 463.49
• Mol File: 106635-80-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 565.6°Cat760mmHg
• Flash Point: 295.9°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 8.17E-13mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 4°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.36±0.10(Predicted)
• CAS DataBase Reference: Tafenoquine(CAS DataBase Reference)
• NIST Chemistry Reference: Tafenoquine(106635-80-7)
• EPA Substance Registry System: Tafenoquine(106635-80-7)

Safety Data

• Hazardous Substances Data: 106635-80-7(Hazardous Substances Data)

Usage

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.

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.

InChI:InChI=1/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

Upstream product

• 106635-81-8 8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate 
• 622405-66-7 8-[(1-methyl-4-nitrobutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 
• 82333-41-3 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 
• 106635-87-4 2,6-dimethoxy-4-methyl-8-<(4-phthalimido-1-methylbutyl)amino>-5-<3-(trifluoromethyl)phenoxy>quinoline 
• 106635-83-0 6-methoxy-4-methyl-8-phthalimido-5-<3-(trifluoromethyl)phenoxy>quinoline 1-oxide 
• 106635-84-1 2-chloro-6-methoxy-4-methyl-8-phthalimido-5-<3-(trifluoromethyl)phenoxy>quinoline 
• 106635-82-9 6-methoxy-4-methyl-8-phthalimido-5-<3-(trifluoromethyl)phenoxy>quinoline 
• 106635-86-3 8-amino-2,6-dimethoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline 
• 106635-85-2 8-amino-2-chloro-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline 

Downstream Products

• 106635-81-8 8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate 

Related news

Interactions between Tafenoquine (cas 106635-80-7) and artemisinin-combination therapy partner drug in asexual and sexual stage Plasmodium falciparum08/02/2019

The 8-aminoquinoline tafenoquine (TFQ), a primaquine derivative, is currently in late-stage clinical development for the radical cure of P. vivax. Here drug interactions between TFQ and chloroquine and six artemisinin-combination therapy (ACT) partner drugs in P. falciparum asexual stages and ga...detailed

Tafenoquine (cas 106635-80-7) is not neurotoxic following supertherapeutic dosing in rats08/01/2019

BackgroundTafenoquine is a new drug for malaria prevention. The goal of the present work was to conduct a specific neurobehavioral study in rats with histopathological assessment of the brain.detailed

Tafenoquine (cas 106635-80-7) for malaria prophylaxis in adults: An integrated safety analysis07/31/2019

BackgroundTafenoquine is a new prophylactic antimalarial drug. The current analysis presents an integrated safety assessment of the Tafenoquine Anticipated Clinical Regimen (Tafenoquine ACR) from 5 clinical trials, including 1 conducted in deployed military personnel and 4 in non-deployed reside...detailed

Relevant articles and documents

An antimalarial drug, tafenoquine, as a fluorescent receptor for ratiometric detection of hypochlorite

Tafenoquine (TQ), a fluorescent antimalarial drug, was used as a receptor for the fluorometric detection of hypochlorite (OCl-). TQ itself exhibits a strong fluorescence at 476 nm, but OCl--selective cyclization of its pentan-1,4-diamine moiety creates a blue-shifted fluorescence at 361 nm. This ratiometric response facilitates rapid, selective, and sensitive detection of OCl- in aqueous media with physiological pH. This response is also applicable to a simple test kit analysis and allows fluorometric OCl- imaging in living cells.

Antimalarials. 16. Synthesis of 2-substituted analogues of 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3- (trifluoromethyl)phenoxy]quinoline as candidate antimalarials

A series of 2-substituted analogues of the exceptional drug 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3- (trifluoromethyl)phenoxy]quinoline (I) were prepared and evaluated for both suppressive and prophylactic antimalarial activity. The preparation of analogues of compound I was of interest due to the high level of both blood and tissue schizonticidal activity demonstrated by this compound. One analogue, 8a, was found to be both more active and less toxic than the parent compound I. In addition, three analogues of example 8a were prepared. Although two of the three analogues showed significant antimalarial activity, both were inferior to compound 8a.