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Chemistry

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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

Tafenoquine Succinate

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 Formula	C₂₈H₃₄F₃N₃O₇
Molecular Weight	581.6 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	12
Exact Mass	581.23488492 g/mol
Monoisotopic Mass	581.23488492 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	690
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)

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