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    Tafenoquine Succinate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 106635-81-8, Wr-238605, Tafenoquine succinate [usan], Tafenoquine (succinate), Dl5j0b8vss, 106635-81-8 (succinate)
    Molecular Formula
    C28H34F3N3O7
    Molecular Weight
    581.6  g/mol
    InChI Key
    CQBKFGJRAOXYIP-UHFFFAOYSA-N
    FDA UNII
    DL5J0B8VSS
    Tafenoquine Succinate is the succinate salt form of tafenoquine, an orally bioavailable 8-aminoquinoline derivative, with antimalarial activity. Although the mechanism is not completely understood, upon administration, tafenoquine inhibits the parasitic enzyme heme polymerase in the blood stages of the parasites. This inhibits the conversion of the toxic heme into non-toxic hemazoin, thereby resulting in the accumulation of toxic heme within the parasite. Tafenoquine is active against all the stages of Plasmodium species and is also active against the pre-erythrocytic liver stages of the parasites. This prevents the development of the erythrocytic forms of the parasite which are responsible for relapses in P. vivax malaria.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    butanedioic acid;4-N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
    2.1.2 InChI
    InChI=1S/C24H28F3N3O3.C4H6O4/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;5-3(6)1-2-4(7)8/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3;1-2H2,(H,5,6)(H,7,8)
    2.1.3 InChI Key
    CQBKFGJRAOXYIP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC.C(CC(=O)O)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    DL5J0B8VSS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (r)-tafenoquine Succinate

    2. Arakoda

    3. Butanedioic Acid, Compd. With N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1)

    4. Butanedioic Acid, Compd. With N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1), (r)-

    5. Krintafel

    6. N(4)-(2,6-dimethoxy-4-methyl-5-((3-trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine

    7. Sb-252263-ax

    8. Sb-252263ax

    9. Sb252263-ax

    10. Sb252263ax

    11. Tafenoquine

    12. Tafenoquine Maleate

    13. Tafenoquine Succinate, (r)-

    14. Wr 238605

    15. Wr-238605

    16. Wr238605

    2.3.2 Depositor-Supplied Synonyms

    1. 106635-81-8

    2. Wr-238605

    3. Tafenoquine Succinate [usan]

    4. Tafenoquine (succinate)

    5. Dl5j0b8vss

    6. 106635-81-8 (succinate)

    7. Arakoda

    8. Krintafel

    9. Sb-252263-ax

    10. Wr238605 Succinate

    11. Butanedioic Acid, Compd. With N4-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinyl]-1,4-pentanediamine (1:1)

    12. Tafenoquine Succinate (usan)

    13. N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine Succinate

    14. N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine Succinate(1:1)

    15. Unii-dl5j0b8vss

    16. Sb-252263

    17. Krintafel (tn)

    18. Butanedioic Acid, Compd. With N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1)

    19. Arakoda (tn)

    20. Wr 238605 Succinate

    21. Butanedioic Acid, Compd. With N(sup 4)-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-1,4-pentanediamine (1:1)

    22. Mls006010680

    23. Wr 238605 (succinate)

    24. Schembl1004186

    25. Chembl2364635

    26. Dtxsid10910065

    27. Tafenoquine Succinate [mi]

    28. Akos037648507

    29. Tafenoquine Succinate [who-dd]

    30. Hy-111529a

    31. Tafenoquine Succinate, >=95% (hplc)

    32. Bs-14295

    33. Butanedioic Acid;4-n-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine

    34. Smr004701662

    35. Tafenoquine Succinate [orange Book]

    36. Cs-0083862

    37. D10670

    38. D80913

    39. A904698

    40. Q27276464

    41. (4rs)-n4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine Butanedioate

    42. 8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline Succinate

    43. 8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinoline Succinate

    44. N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diaminesuccinate(1:1)

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 581.6 g/mol
    Molecular Formula C28H34F3N3O7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count12
    Exact Mass581.23488492 g/mol
    Monoisotopic Mass581.23488492 g/mol
    Topological Polar Surface Area153 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity690
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antimalarials

    Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)