Chem Basis CPN structures 2

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Chem Basis CPN structures 2
2014-01-26 15:25:31
Chem Basis CPN structures

Chem Basis CPN structures 2
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    What is this drug?

  2. What is this drug?

  3. 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

  4. (True/False) incorporating the C alpha into a ring structure will enhance activity.
    False, it inactivates the structure

  5. R2 has what effect on CPN activity?
    Determines acid/base stability

  6.  An acetoxymethyl R2 has what effect on the molecule?
    Makes the structure: acid labile (no PO) and 20% inactivated by hepatic and renal esterases

  7.  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)

  8. which of these compound scan you give orally if the alpha carbon has a polar substituent?
    The one with NH2 (carbamoxymethyl)

  9.  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

  10.  This compound is acid labile, though less than acetoxymethyl, how can you make it orally available?
    Add a polar substituent to the alpha carbon

  11.  What is this group called?
    Pyridinium methyl

  12. What is this group called?

  13. What is this group called?

  14. This group imparts what characteristics on the CPN?
    Vulnerable to base-catalyzed degredation and H20 catalyzed degredation, which increases w/ increasing pH

  15. 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)

  16. What characteristics does this group at R2 impart on the CPN?
    Inactive (lactone)

  17. Which CPN has this R2 group?

  18. What is this group and which CPN has this R2 group?
    Cefamandole, cefotetan, cefmetazole, moxalactam and cefoperazone ( group is called Methyltetrazolethiol, MTT)

  19. 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)

  20. does this substituent (MTT) have any benefits?
    Yes, increases antimicrobial activity

  21. Highly polar R2 groups like these have what enhance activity?
    Enhanced G- activity

  22. 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.

  23. (True/False) A carbamoxymethyl with a polar group for R' and a prodrug form provide for oral activity.

  24. The CPN C3-4 double bond has what characteristics?
    Essential for activity and enhances acid stability

  25. What can R3 be?
    H or a Methoxy group

  26. An alpha-methoxy group at R3 has what effect on the molecule?
    Creates a cephamycin and confers broad resistance to B-lactamases