Vonoprazan

Synopsis, Chemistry

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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 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

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 Formula	C₂₁H₂₀FN₃O₆S
Molecular Weight	461.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	461.10568470 g/mol
Monoisotopic Mass	461.10568470 g/mol
Topological Polar Surface Area	147 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	629
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2