Drug Details

General Information of the Drug (ID: DR9623)
Name
Tafenoquine
Synonyms
Tafenoquine; 106635-80-7; Etaquine; WR 238605; Tafenoquine free base; SB-252263-AAB; 106635-80-7 (free base); WR238605; 4-N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine; Krintafel; N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine; 1,4-Pentanediamine, N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-; SB-252263; Arakoda; Tafenoquine [USAN:INN:BAN]; 1,4-Pentanediamine, N4-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinyl]-; N(4)-(2,6-Dimethoxy-4-methyl-5-((3-trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine; Tafenoquine (USAN); (R)-N3-(2,6-Dimethoxy-4-methyl-5-(3-trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine; SCHEMBL347388; CHEMBL298470; GTPL9722; CHEBI:141487; EX-A3146; DB06608; SB16555; (RS)-N(sup 3)-(2,6-Dimethoxy-4-methyl-5-(3-trifluoro-methylphenoxy)quinolin-8-yl)pentane-1,4-diamine; HY-111529; CS-0042381; FT-0775258; D10490; Q2387553; N4-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolyl]pentane-1,4-diamine; (+/-)-8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy) quinoline; (4-Amino-1-methylbutyl){2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy](8-quinolyl)}amine; N(4)-{2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl}pentane-1,4-diamine
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Molecular Type
Small molecule
Disease Malaria [ICD-11: 1F40] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C24H28F3N3O3
PubChem CID
115358
Canonical SMILES
CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC
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
CAS Number
CAS 106635-80-7
ChEBI ID
CHEBI:141487
TTD Drug ID
D07TWN
DrugBank ID
DB06608
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
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          Artesunate      Artemisia annua     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Increase Rapid clearance of B. microti
                    In-vitro Model Babesia bovis Microorganism model Babesia bovis
                    In-vivo Model 8-9-weeks-old BALB/c female mice were used in this study.
                    Experimental
                    Result(s)		 Tafenoquine (10 mg/kg, base), combined or not with artesunate, but not mefloquine, induced rapid clearance of B. microti in vivo by microscopy, but mice remained PCR-positive.
Target and Pathway
Target(s) Cytochrome bc1 complex (Complex III)  Molecule Info  [1]
References
Reference 1 Tafenoquine: First Global Approval.Drugs. 2018 Sep;78(14):1517-1523.
Reference 2 Activities of artesunate-based combinations and tafenoquine against Babesia bovis in vitro and Babesia microti in vivo. Parasit Vectors. 2020 Jul 20;13(1):362.
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