Chem Basis CPN structures 2

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    What is this drug?
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    What is this drug?
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    What differences in chemistry and activity do these groups impart?
    The methoxyimino group on cefepime is less polar and so has greater antistaphylococcal activity. The 2-carboxyl-2propoxyimino group is too polar and limits G+ activity
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    (True/False) incorporating the C alpha into a ring structure will enhance activity.
    False, it inactivates the structure
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    R2 has what effect on CPN activity?
    Determines acid/base stability
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     An acetoxymethyl R2 has what effect on the molecule?
    Makes the structure: acid labile (no PO) and 20% inactivated by hepatic and renal esterases
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     How does the chemistry and activity of these two R2 groups compare?
    Both are acid lable, but thecarboamoxymethyl is less so, b/c the NH2 is a negative inducer and results in decreased e- density at the ether O, decreasing the rate of protonation over the one carrying a CH3 (acetoxymethyl)
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    which of these compound scan you give orally if the alpha carbon has a polar substituent?
    The one with NH2 (carbamoxymethyl)
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     If you are giving an oral CPN with an R2 carbamoxymethyl and a polar functional group on the alpha carbon, how can you speed up absorption to reduce acid breakdown?
    Crush the tablets and give as a suspension
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     This compound is acid labile, though less than acetoxymethyl, how can you make it orally available?
    Add a polar substituent to the alpha carbon
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     What is this group called?
    Pyridinium methyl
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    What is this group called?
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    What is this group called?
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    This group imparts what characteristics on the CPN?
    Vulnerable to base-catalyzed degredation and H20 catalyzed degredation, which increases w/ increasing pH
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    If a molecule has this substituent at R2, what precautions should you take when preparing it for IV?
    Make fresh solutions, because it is subject to H20-catalyzed degradation (R2 group called Pyridinium methyl)
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    What characteristics does this group at R2 impart on the CPN?
    Inactive (lactone)
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    Which CPN has this R2 group?
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    What is this group and which CPN has this R2 group?
    Cefamandole, cefotetan, cefmetazole, moxalactam and cefoperazone ( group is called Methyltetrazolethiol, MTT)
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    What side effects does Methyltetrazolethiol (MTT) R2 group cause?
    Dislfiram like reaction resulting in N/V and hypotension. Also, hypoprothrombinemia and Vit. K deficiency (results in increased bleeding)
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    does this substituent (MTT) have any benefits?
    Yes, increases antimicrobial activity
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    Highly polar R2 groups like these have what enhance activity?
    Enhanced G- activity
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    What type of R2 group would help promote increased stability and oral activity?
    Those with small, non-ionizable functional groups, like: CH3, Cl, -CH=CH2 and –CH=CH-CH3.
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    (True/False) A carbamoxymethyl with a polar group for R' and a prodrug form provide for oral activity.
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    The CPN C3-4 double bond has what characteristics?
    Essential for activity and enhances acid stability
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    What can R3 be?
    H or a Methoxy group
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    An alpha-methoxy group at R3 has what effect on the molecule?
    Creates a cephamycin and confers broad resistance to B-lactamases
Card Set:
Chem Basis CPN structures 2
2014-01-26 20:25:31
Chem Basis CPN structures

Chem Basis CPN structures 2
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