Chem Basis PPIs 4

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    Why can pantoprazole form a water soluble salt?
    It’s imidazole NH group is uniquely acidic enough
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    What functional significance does the Methoxy group at R1 have?
    Donates e- to pyridine N through pi bonds
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    What functional significance does the Methoxy group at R2 have?
    Exerts inductive penalty, pulls electrons through sigma bonds, ↓ pKa 1 and ↓ activity
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    What effect does the 5-difluromethoxy group have on the Benzimidazole N3?
    ↓ ability of N3 to become protonated
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    Why is the activation of this drug slow?
    Due to low reactivity of the benzimidazole N3
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    The slow activation of pantoprazole allows for what?
    The drug to reach the deeper CYS residue
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    Why is the duration of action longer for Pantoprazole than other PPIs?
    The deeper CYS residue is bound, parietal cells are not subject to glutathione rescue
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    What CYP enzymes metabolize Pantoprazole?
    CYP2C19 and CYP3A4
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    How does CYP2C19 alter this drug?
    O-dealkylation of the C5 methoxy
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    How does CYP3A4 alter this drug?
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    What significant DDIs does this drug have?
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Chem Basis PPIs 4
Chem Basis PPIs 4
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