Chem Basis PPIs 2

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  1. What functional significance does the methoxy group at position 4 (R1) have?
    Donates electrons through resonance to pyridine nitrogen (Omeprazole)

  2. What functional significance do the methyl groups at positions 3 and 5 have?
    ↑nucleophilic character of unionized pyridine N by ↓ inductive pull of the methoxy group on the pyridine N (Omeprazole)

  3. What is the functional significance of the methoxy group at position 5 of Benzimidazole ring?
    Enhances N3 protonation, pulls e- from C2 through sigma bonds (Omeprazole)

  4. What is the relative OOA for Omeprazole? Fast

  5. Can this molecule reach the deeper CYS residue?
    No (Omeprazole)

  6. Does this drug have a long or short DOA?
    Long (Omeprazole)

  7. Is this molecule susceptible to Glutathione rescue?
    Yes (Omeprazole)

  8. Is this drug susceptible to CYP2C19 metabolism?
    Yes (Omeprazole)

  9. What changes to this molecule would CYP2C19 make?
    Hydroxylation of C5 (Omeprazole)

  10. Is this drug susceptible to CYP3A4 metabolism?
    Yes (Omeprazole)

  11. What changes to this molecule would CYP3A4 make?
    Sulfoxidation to a sulfone (Omeprazole)

  12. Which CYP enzyme catalyzes the reduction of this drug to a Thioether?
    None, occurs by a non-enzymatic reaction (Omeprazole)

  13. What effect does this drug have on CYP2C19?
    Can inhibit it when dosed chronically (in turn inhibiting own metabolism) (Omeprazole)

  14. What is the only clinically significant DDI for this drug?
    Causes 25-50% ↓ in diazepam clearance (Omeprazole)

  15. In what race would you need to decrease the dose of this drug and why?
    Asians as b/c typically slow CYP2C19 metabolizers (Omeprazole)

Card Set Information

Chem Basis PPIs 2
2013-12-08 20:06:40
Chem Basis PPIs

Chem Basis PPIs 2
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