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    Tegoprazan

    ACTIVE PHARMA INGREDIENTS

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    DIGITAL CONTENT

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    2D Structure
    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

    2D Structure

    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 Weight 387.4 g/mol
    Molecular Formula C20H19F2N3O3
    XLogP33.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass387.13944780 g/mol
    Monoisotopic Mass387.13944780 g/mol
    Topological Polar Surface Area67.4 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity581
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.