fg55 Flashcards
(4 cards)
How can amide hydrolysis be detrimental to drug pharmacology? (Example: Penicillins)
Penicillins contain a β-lactam amide bond, which is hydrolyzed by β-lactamase enzymes in resistant bacteria. This inactivates the drug, reducing its antibacterial effectiveness.
What is the general reactivity order of carbonyl-containing functional groups?
Aldehyde > Ketone > Ester > Amide
Aldehydes are most reactive due to less steric hindrance and no electron-donating groups. Ketones are slightly less reactive due to steric hindrance. Esters are less reactive due to resonance stabilization and electron-donating effects. Amides are the least reactive due to strong resonance between the nitrogen and carbonyl oxygen.
Why are amides less reactive than esters?
Stronger resonance in amides makes the carbonyl carbon less electrophilic. Weaker leaving group (-NH₂ vs. -OR) makes hydrolysis less favorable.
How do hydrolysis differences between esters and amides affect drug action? (Example: Anaesthetics)
Ester-based anaesthetics (e.g., procaine) are hydrolyzed quickly, leading to a shorter duration of action. Amide-based anaesthetics (e.g., lidocaine) are hydrolyzed much slower, resulting in longer-lasting effects.
