Chem Basis PPIs 1

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Author:
kyleannkelsey
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251685
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Chem Basis PPIs 1
Updated:
2013-12-08 15:03:20
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Chem Basis PPIs
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Chem Basis PPIs 1
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  1. What is the pharmacophore is for all currently marketed PPIs?
  2. 2-pyridylmethylsulfinylbenzimidazole
  3. Differences between various PPIs are found in what areas of the pharmacophore?
  4. Substituents placed on the pyridine and benzimidazole rings
  5. (True/False) The Sulfinyl moiety on PPI parent drugs is sufficiently reactive to form essential disulfide bond with proton pump CYS residues.
    False, is not sufficienly reactive enough (prodrugs)
  6. Are PPIs active or prodrugs in the parent form?
    Prodrugs
  7. Do PPIs require enzymatic activation?
    No
  8. What form will PPIs be in in the blood stream, ionized or unionized?
    Completely unionized
  9. What form will PPIs be in in the stomach, ionized or unionized?
    Highly ionized
  10. What are the functions of the electron donating groups on the PPI pharamcophore?
    ↑ % of pyridine N existing in ionized form, ↑ nucleophilic character of pyridine N in unionized form, ↑rate of formation of active sulfenic acid/sulfonamide rearrangement products

  11. How does the pKa of the benzidamazole N3 relate to the Pyridine N?
    Benzidamazole N3 has a lower pKa than the Pyridine N

  12. How does the pKa of the benzidamazole N3 relate to the pKa of the parietal cells?
    Benzidamazole N3 has a lower pKa than the Parietal Cells

  13. Which ring is protonated first:
    First the pyridine ring, then the Benzimidazole ring
  14. Why is it important that the benzimidazole N3 is cationic?
    Critical to PPI activation, ↑electrophilicity of C2 by pulling the e- through the sigma bonds, which ↑intramolecular attack

  15. Why is it important that e- donating substituents are present on C5 of the benzimidazole ring?
    They push electrons to the N3, increasing the % existing in the cationic form

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