Chem Basis CPN structures 1

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    If you swap a C for the S in the CPN pharmacophore, is it tolerated?
    Yes, called a carbacephem
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    What is the benefit to having this ring structure
    Essential for activity and enhanced B-lactamase resistance
  3. Image UploadHow does the 3-cephem ring compare to a PCN?
    Less strained
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     (True/False) This is a 7-aminocephalosporonic acid.
    True
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    (True/False) This structure contains a beta-lactam and dihydrothiazine structure (i.e. 3-cephem).
    True
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    (True/False) Substituting the -S with a -C produces a cephamycin
    False, produces a Carbacephem
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    is this structure essential for activity?
    Yes
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    Which drugs are cephamycins?
    Cefoxiten and Cefotetan
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    What is the advantage of a cephamycin?
    Broader resistance to B-lactamases
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    Is the COOH essential for activity?
    Yes
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    How does the COOH work to maintain activity of the CPN?
    Anchors the CPN to the cell wall and orients it to acylate the transpeptidase
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    Can the COOH of CPNs form water soluble salts?
    Yes
  13. Image Upload For all marketed forms of CPNs, what form is the COOH in and why?
    Na+ salt, for IV administration
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    What characteristics of the CPN are affected by R1?
    Spectrum, B-lactamas ressitance, oral bioavailability
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    Is acid stability affected by R1?
    No
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    Like with penicillins, does a lipophilic R group cause increased G+ activity?
    Yes
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    What generation of CPNs would have a lipophilic ring at R or R’?
    1st and 2nd generation
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    What generation of CPNs would ou expect to see more polar rings at R or R’?
    3rd and 4th generation
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    What is this potential R group called?
    2-amino thiazole
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    Most 3rd and 4th generation CPNs have what group for R’?
    Methoxyimine
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    What is this group?
    Methoxyimine
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    These methoxyimine variations have what effect as an R’ group on a CPN?
    Add G- coverage due to polarity
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    Polar groups at R1 have what effect on oral absorption?
    Enhance oral absorption in acid stable compounds
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    Comparing an NH2 and a methoxyimine at R’, which one would be better at preventing intermolecular opening of the B-lactam ring (enhancing stability of the B-lactam)?
    Methoxyimine
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    How do methoxyimine variations enhance B-lactamase resistance of a CPN?
    Steric hindrance
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    How can a Methoxyimine group be further modified to enhance B-lactamase resistance?
    Add a polar functional group to it (e.g. COOH)

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Author:
kyleannkelsey
ID:
258470
Filename:
Chem Basis CPN structures 1
Updated:
2014-01-26 20:18:14
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Chem Basis CPN structures
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Chem Basis CPN structures 1
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