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Tegoprazan

Tegoprazan

Synopsis, Chemistry

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Also known as: 942195-55-3, Tegoprazan [inn], W017g7if4s, Lxi-15028, (s)-4-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzo[d]imidazole-6-carboxamide, 1h-benzimidazole-5-carboxamide, 7-(((4s)-5,7-difluoro-3,4-dihydro-2h-1-benzopyran-4-yl)oxy)-n,n,2-trimethyl-

Molecular Formula

C₂₀H₁₉F₂N₃O₃

Molecular Weight

387.4 g/mol

InChI Key

CLIQCDHNPDMGSL-HNNXBMFYSA-N

FDA UNII

W017G7IF4S

Tegoprazan (also known as CJ-12420) is a novel therapeutic developed by CJ Healthcare Corp for treating acid-related gastrointestinal diseases. This drug is a potent and high-selective potassium-competitive acid blocker (P-CAB) with a fast onset of action and the ability to control gastric pH for a prolonged period of time. Tegoprazans strong and sustained effect is due to its ability to be slowly cleared from the gastric glands and exertion of effects independent of acid levels. It has also been observed to be efficacious independent of food intake.

1 2D Structure

Tegoprazan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-[[(4S)-5,7-difluoro-3,4-dihydro-2H-chromen-4-yl]oxy]-N,N,2-trimethyl-3H-benzimidazole-5-carboxamide

2.1.2 InChI

InChI=1S/C20H19F2N3O3/c1-10-23-14-6-11(20(26)25(2)3)7-17(19(14)24-10)28-15-4-5-27-16-9-12(21)8-13(22)18(15)16/h6-9,15H,4-5H2,1-3H3,(H,23,24)/t15-/m0/s1

2.1.3 InChI Key

CLIQCDHNPDMGSL-HNNXBMFYSA-N

2.1.4 Canonical SMILES

CC1=NC2=C(N1)C=C(C=C2OC3CCOC4=C3C(=CC(=C4)F)F)C(=O)N(C)C

2.1.5 Isomeric SMILES

CC1=NC2=C(N1)C=C(C=C2O[C@H]3CCOC4=C3C(=CC(=C4)F)F)C(=O)N(C)C

2.2 Other Identifiers

2.2.1 UNII

W017G7IF4S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (s)-4-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzo(d)imidazole-6-carboxamide

2. 1h-benzimidazole-5-carboxamide, 7-(((4s)-5,7-difluoro-3,4-dihydro-2h-1-benzopyran-4-yl)oxy)-n,n,2-trimethyl-

3. 7-(((4s)-5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)oxy)-n,n,2-trimethyl-1h-benzimidazole-5-carboxamide

2.3.2 Depositor-Supplied Synonyms

1. 942195-55-3

2. Tegoprazan [inn]

3. W017g7if4s

4. Lxi-15028

5. (s)-4-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzo[d]imidazole-6-carboxamide

6. 1h-benzimidazole-5-carboxamide, 7-(((4s)-5,7-difluoro-3,4-dihydro-2h-1-benzopyran-4-yl)oxy)-n,n,2-trimethyl-

7. Unii-w017g7if4s

8. Emixustat Hcl

9. (s)-4-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzo(d)imidazole-6-carboxamide

10. 7-[[(4s)-5,7-difluoro-3,4-dihydro-2h-chromen-4-yl]oxy]-n,n,2-trimethyl-3h-benzimidazole-5-carboxamide

11. K-cab

12. Tegoprazan [who-dd]

13. Schembl2687723

14. Chembl4297583

15. Schembl19236298

16. Gtpl12008

17. (s)-7-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzo(d)imidazole-5-carboxamide

18. Ex-a4304

19. Cj12420

20. Ac-36576

21. As-84160

22. Cj-12420

23. Hy-17623

24. Cs-0014702

25. E83739

26. Cj-12420; In-a001; Lxi-15028

27. Q27292116

28. (-)-4-[((4s)-5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)oxy]-n,n,2-trimethyl-1h-benzimidazole-6-carboxamide

29. 7-(((4s)-5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)oxy)-n,n,2-trimethyl-1h-benzimidazole-5-carboxamide

30. 7-[[(4s)-5,7-difluoro-3,4-dihydro-2h-1-benzopyran-4-yl]oxy]-n,n,2-trimethyl-1h-benzimidazole-5-carboxamide

31. 8bn

2.4 Create Date

2007-12-10

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉F₂N₃O₃
Molecular Weight	387.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	387.13944780 g/mol
Monoisotopic Mass	387.13944780 g/mol
Topological Polar Surface Area	67.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	581
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 ATC Code

A - Alimentary tract and metabolism

A02 - Drugs for acid related disorders

A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

A02BC - Proton pump inhibitors

A02BC09 - Tegoprazan

4.2 Mechanism of Action

Tegoprazan works as a potassium-competitive acid blocker that is potent and highly selective. Its mechanism of action is different from that of the proton-pump inhibitors as this drug does not require conversion into an active form and can directly inhibit H+/K+ATPase in a reversible and K+competitive way. This is because it is an acid-resistant weak base with the ability to remain in the highly acidic canaliculi of gastric parietal cells.