Chem Basis ACEIs and ARBs Structures 3

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kyleannkelsey
ID:
250117
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Chem Basis ACEIs and ARBs Structures 3
Updated:
2013-12-02 00:14:18
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Chem Basis ACEIs ARBs Structures
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Chem Basis ACEIs and ARBs Structures 3
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  1. What is the pharamcophore of this compound (Enalapril)?
    N-carboxymethy L-alanyl-L-proline derivative

  2. The phenyl ethyl group side chain has what effect on this molecules action, why?
    Enhances activity by allowing hydrophobic/Van der Waals binding to the auxiliary binding site (Enalapril)

  3. The ester on the side chain carboxylic group indicates that what must happen prior to binding?
    Hydrolysis of the ester to free an OH group (Enalapril)

  4. Is this an active drug?
    No, a Prodrug (Enalapril)

  5. The ester also has what effect on this molecules activity?
    Increased oral absorption and bioavailability (resulting in once a day dosing)

    (Enalapril)

  6. The cyclic nature of the proline provides for what benefit?
    An amide bond that is protected and not easily hydrolyzed by amidases

    (Enalapril)

  7. The carbonyl oxygen may be involved with what type of interaction with the receptor?
    Hydrogen binding

    (Enalapril)

  8. The methyl on the side chain may be involved with what type of interaction with the receptor
    Hydrophobic binding

    (Enalapril)

  9. The NH is critical for activity because it provides what benefit?
    H-binding to ACE

    (Enalapril)

  10. What is this drug?
    Enalapril

  11. What is the pharamcophore of this molecule(Fosinopril)?
    Phosphinyl acetyl L-proline derivative

    (Fosinapril)

  12. What must happen for this molecule to bind to the receptor?
    Hydrolysis of the phosphinyl group and ester

    (Fosinapril)

  13. Can this molecule bind at the zinc binding site?
    No, needs t oundergo hydrolysis at the phosphinyl group

    (Fosinapril)

  14. Is this an active drug?
    No, A prodrug

    (Fosinapril)

  15. How often is this drug dosed and why?
    Once daily because it is an prodrug (see ester and phosphinyl group)

    (Fosinapril)

  16. The cyclohexane on the proline is tolerated and may contribute to what?
    Hydrophobic binding to ACE

    (Fosinapril)

  17. The phenyl butyl group on the side chain has what effect on activity?
    Enhances activity by binding to the auxiliary binding site via hydrophobic and Van der Waals forces

    (Fosinapril)

  18. What is this drug?
    Losartan, and ARB, nonpeptide antagonist/blocker of one of the angiotensin receptors

  19. What is the pharamcophore of this drug?
    1-N-benzyl 2-butyl Imidazole

    (Losartan)

  20. What effect does the imidazole ring have on this drug?
    Allows for better binding to Ag-II receptor (AT1)

    (Losartan)

  21. The phenyltetrazole acidic group contributes to what effects of this drug?
    Enhances binding to Ag-II receptor, metabolic stability, lipophilicity and oral bioavailability

    (Losartan)

  22. What configuration should the tetrazole be in for optimal binding?
    Ortho position

    (Losartan)

  23. A lack of linker between the two phenyls has what effect on this molecule?
    Good oral activity

    (Losartan)

  24. The 2-butyl group has what effect on this molecule?
    Maintains activity

    (Losartan)

  25. The methyl alcohol on the imidazole ring is also goodor bad for activity?
    Good

    (Losartan)

  26. Is the parent structure is active?
    Yes

    (Losartan)

  27. What is the half-life of the parent structure?
    Short half life (1.5-2.5 hr)

    (Losartan)

  28. The parent structure is oxidized to an active 5-carboxylic acid metabolite, what activity does it have?
    10-40 times the potentency and a longer half life (6-9 hr)

    (Losartan)

  29. The active 5-carboxylic acid metabolite provides for what dosing schedule?
    Increased to once or twice a day dosing

    (Losartan)

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