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Also known as: Tak-438, 1260141-27-2, 881681-01-2, Vonoprazan fumurate, 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine fumarate, Tak 438
Molecular Formula
C21H20FN3O6S
Molecular Weight
461.5  g/mol
InChI Key
ROGSHYHKHPCCJW-WLHGVMLRSA-N
FDA UNII
4QW3X4AMLB

Vonoprazan Fumarate
Vonoprazan Fumarate is the fumarate salt form of vonoprazan, a pyrrole derivative and reversible potassium-competitive acid blocker (P-CAB), with potential antacid activity. Upon administration, vonoprazan specifically and competitively binds to the gastric hydrogen-potassium ATPase (H+/K+ ATPase) proton pump at or, more likely, near its potassium ion (K+) binding site and sterically inhibits K+ binding. This blocks the activation of the H+/K+ ATPase by K+, inhibits the proton pump and prevents gastric acid secretion, thereby lowering gastric acid levels.
1 2D Structure

Vonoprazan Fumarate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-but-2-enedioic acid;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine
2.1.2 InChI
InChI=1S/C17H16FN3O2S.C4H4O4/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14;5-3(6)1-2-4(7)8/h2-9,11-12,19H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
2.1.3 InChI Key
ROGSHYHKHPCCJW-WLHGVMLRSA-N
2.1.4 Canonical SMILES
CNCC1=CN(C(=C1)C2=CC=CC=C2F)S(=O)(=O)C3=CN=CC=C3.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
CNCC1=CN(C(=C1)C2=CC=CC=C2F)S(=O)(=O)C3=CN=CC=C3.C(=C/C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
4QW3X4AMLB
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine

2. Tak 438

3. Tak-438

4. Tak438

5. Vonoprazan

2.3.2 Depositor-Supplied Synonyms

1. Tak-438

2. 1260141-27-2

3. 881681-01-2

4. Vonoprazan Fumurate

5. 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine Fumarate

6. Tak 438

7. Tak-438 Monofumarate

8. Vonoprazan Monofumarate

9. Vonoprazan Fumarate (tak-438)

10. 4qw3x4amlb

11. Tak438

12. Unii-4qw3x4amlb

13. Takecab

14. Vocinti

15. (e)-but-2-enedioic Acid;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-n-methylmethanamine

16. 1h-pyrrole-3-methanamine, 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)-, (2e)-2-butenedioate (1:1)

17. 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine Xfumarate

18. 1h-pyrrole-3-methanamine, 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)-, 2-butenedioate (1:1)

19. Mfcd18633280

20. Vonoprazan Monofumurate

21. 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl]-n-methylmethanamine Fumarate

22. Takecab (tn)

23. Vonoprazan Fumarate [usan]

24. Schembl194394

25. Schembl194396

26. Chembl2064032

27. Vonoprazan Fumarate [mi]

28. Vonoprazan Fumarate (jan/usan)

29. Ex-a097

30. Vonoprazan Fumarate [jan]

31. Bcp05635

32. Bcp13238

33. Ex-a4001

34. S8016

35. Vonoprazan Fumarate [who-dd]

36. Akos027251052

37. Ccg-269350

38. 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine Monofumarate

39. 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)-1h-pyrrole-3-methanamine (2e)-2-butenedioate

40. Ac-29287

41. Ac-29309

42. Ds-12234

43. Ls-14849

44. Cs-0164592

45. Sw220126-1

46. D10466

47. A854789

48. A900258

49. J-524312

50. Q25104163

51. Tak438 Fumarate;tak-438 Fumarate;tak 438 Fumarate;1260141-27-2

52. 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine Fumarate? (vonoprazan Impurity Pound(c)

53. 2098974-13-9

54. 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)-1h-pyrrole-3-methanamine 2-butenedioate

2.4 Create Date
2010-05-17
3 Chemical and Physical Properties
Molecular Weight 461.5 g/mol
Molecular Formula C21H20FN3O6S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Exact Mass461.10568470 g/mol
Monoisotopic Mass461.10568470 g/mol
Topological Polar Surface Area147 Ų
Heavy Atom Count32
Formal Charge0
Complexity629
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2

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