Tafenoquine

Base Information

• Chemical Name: Tafenoquine
• CAS No.: 106635-80-7
• Molecular Formula: C24H28 F3 N3 O3
• Molecular Weight: 463.5
• UNII: 262P8GS9L9
• DSSTox Substance ID: DTXSID90869466
• Nikkaji Number: J350.379H
• Wikipedia: Tafenoquine
• Wikidata: Q2387553
• NCI Thesaurus Code: C73006
• RXCUI: 2054023
• Metabolomics Workbench ID: 149856
• ChEMBL ID: CHEMBL298470
• Mol file: 106635-80-7.mol

Synonyms:(R)-tafenoquine succinate;Arakoda;butanedioic acid, compd. with N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1);butanedioic acid, compd. with N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1), (R)-;Krintafel;N(4)-(2,6-dimethoxy-4-methyl-5-((3-trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine;SB-252263-AX;SB-252263AX;SB252263-AX;SB252263AX;tafenoquine;tafenoquine maleate;tafenoquine succinate;tafenoquine succinate, (R)-;WR 238605;WR-238605;WR238605

Chemical Property of Tafenoquine

Chemical Property:

• Vapor Pressure: 8.17E-13mmHg at 25°C
• Boiling Point: 565.6°Cat760mmHg
• PKA: 10.36±0.10(Predicted)
• Flash Point: 295.9°C
• PSA: 78.63000
• Density: 1.237g/cm³
• LogP: 6.68410
• Storage Temp.: 4°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 463.20827625
• Heavy Atom Count: 33
• Complexity: 597

Purity/Quality:

98%Min ^*data from raw suppliers

Tafenoquine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antimalarial Agents
• Canonical SMILES: CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC
• Recent ClinicalTrials: Southeast Asia Dose Optimization of Tafenoquine
• 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.

Technology Process of Tafenoquine

There total 9 articles about Tafenoquine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate (106635-81-8) → tafenoquine (106635-80-7)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 20 ℃; for 2h;

DOI:10.1039/c7ra04867j

Reference yield:

8-[(1-methyl-4-nitrobutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline (622405-66-7) → tafenoquine (106635-80-7)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In ethanol; at 20 ℃; for 24h; under 750.075 Torr;

Reference yield:

2,6-dimethoxy-4-methyl-8-<(4-phthalimido-1-methylbutyl)amino>-5-<3-(trifluoromethyl)phenoxy>quinoline (106635-87-4) → tafenoquine (106635-80-7)

Guidance literature:

With hydrazine hydrate; In ethanol; water; for 10h; Heating;

DOI:10.1021/jm00128a010

upstream raw materials:

2,6-dimethoxy-4-methyl-8-<(4-phthalimido-1-methylbutyl)amino>-5-<3-(trifluoromethyl)phenoxy>quinoline

8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline

8-amino-2-chloro-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline

8-amino-2,6-dimethoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline

Downstream raw materials:

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