Antibiotics Overview
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Questions and Answers

What is the primary focus of the efforts to improve penicillins?

  • Increasing the sensitivity of the β-lactam ring to acid hydrolysis
  • Minimizing the antibacterial activity
  • Broadening the spectrum of allergic reactions
  • Enhancing pharmacokinetic and microbiological properties (correct)
  • How does varying the acyl side group (R) affect the carbonyl oxygen's nucleophilicity?

  • It decreases the nucleophilicity of the carbonyl oxygen (correct)
  • It completely inhibits the nucleophilicity of the carbonyl oxygen
  • It keeps the nucleophilicity unchanged
  • It enhances the nucleophilicity of the carbonyl oxygen
  • Which of the following penicillins is known for better acid stability and oral activity?

  • Benzylpenicillin
  • Amoxicillin
  • Penicillin G
  • α-aminobenzylpenicillin (ampicillin) (correct)
  • What is a significant drawback of α-aminobenzylpenicillin (ampicillin)?

    <p>It is sensitive to β-lactamases</p> Signup and view all the answers

    Which structural modification is NOT mentioned as an acyl side group for penicillins?

    <p>Cl</p> Signup and view all the answers

    What property does the ammonium group in α-aminobenzylpenicillin contribute?

    <p>Acts as an electron-withdrawing group</p> Signup and view all the answers

    Which of the following penicillins is significantly more stable in acid solutions compared to benzylpenicillin?

    <p>Oxacillin</p> Signup and view all the answers

    How does the presence of electronegative oxygen affect the nucleophilicity of the carbonyl oxygen in penicillins?

    <p>It decreases nucleophilicity</p> Signup and view all the answers

    Which bacteria are generally susceptible to amoxicillin and ampicillin?

    <p>Escherichia and Klebsiella</p> Signup and view all the answers

    Which characteristic makes ampicillin and amoxicillin less effective?

    <p>Production of b-lactamases</p> Signup and view all the answers

    What is a disadvantage of the broad-spectrum activity of ampicillin and amoxicillin?

    <p>They disrupt gut flora</p> Signup and view all the answers

    Which statement is true about the absorption of amoxicillin and ampicillin?

    <p>They have poor absorption through the gut wall</p> Signup and view all the answers

    Which modification is suggested to extend the spectrum of activity for penicillin derivatives?

    <p>Incorporate an acidic substituent</p> Signup and view all the answers

    What is the main structure present in penicillin that is fused with the thiazolidine ring?

    <p>Beta-lactam ring</p> Signup and view all the answers

    Which of the following correctly describes the angle between the beta-lactam ring and the thiazolidine ring in penicillin G?

    <p>117°</p> Signup and view all the answers

    Which component is crucial in the formation of semi-synthetic penicillins?

    <p>6-Aminopenicillanic acid</p> Signup and view all the answers

    What is a significant limitation in using the fermentation method for producing penicillins?

    <p>It is tedious and time-consuming.</p> Signup and view all the answers

    What is clavulanic acid primarily known for?

    <p>Acting as a beta-lactamase inhibitor</p> Signup and view all the answers

    Which of the following penicillins is the first orally active penicillin?

    <p>Penicillin V</p> Signup and view all the answers

    In the structure of penicillin, which two amino acids can be found in the peptidic composition of the penam ring?

    <p>Cysteine and Valine</p> Signup and view all the answers

    Which growth medium is a by-product of corn wet-milling and important for culturing Penicillium?

    <p>Corn steep liquor</p> Signup and view all the answers

    What is the first step in making the side chain more reactive?

    <p>Activate the side chain</p> Signup and view all the answers

    Which nitrogen reaction cannot occur due to the electron pair orientation?

    <p>Beta-lactam nitrogen</p> Signup and view all the answers

    Which compound is mentioned as the product of the reaction involving the amide side chain?

    <p>6-aminopenicillanic acid (6APA)</p> Signup and view all the answers

    In the context of semisynthetic penicillins, which part serves as the framework?

    <p>Bicyclic penicillin nucleus</p> Signup and view all the answers

    What is the effect of introducing a lone pair from nitrogen in reactions involving PCl5?

    <p>Facilitates substitution reactions</p> Signup and view all the answers

    What nomenclature describes penicillins according to the Chemical Abstracts system?

    <p>5-acylamino-2,2-dimethylpenam-3-carboxylic acids</p> Signup and view all the answers

    Which reagent is mentioned as being used in conjunction with the reaction of the side chain?

    <p>PCl5</p> Signup and view all the answers

    Why is the amide nitrogen in a penicillin side chain selective for reactions?

    <p>It is more basic than the β-lactam nitrogen</p> Signup and view all the answers

    Which reaction condition limits the reactivity of β-lactam nitrogen?

    <p>Electron pair orientation</p> Signup and view all the answers

    Which of the following statements about 6-APA is correct?

    <p>It is a key intermediate in penicillin synthesis</p> Signup and view all the answers

    What is a characteristic of oxacillin compared to cloxacillin?

    <p>Oxacillin binds more to plasma proteins than cloxacillin.</p> Signup and view all the answers

    Which of the following factors limit the range of activity of antibiotics?

    <p>Presence of b-lactamases</p> Signup and view all the answers

    How does increasing hydrophilic character in the side chains affect Gram-negative bacteria?

    <p>It significantly increases the activity against Gram-negative bacteria.</p> Signup and view all the answers

    What is the primary reason that certain antibiotics are orally inactive?

    <p>Acid sensitivity due to the absence of electron-withdrawing groups.</p> Signup and view all the answers

    What is a common feature of flucloxacillin compared to oxacillin?

    <p>Flucloxacillin is less affected by plasma protein binding.</p> Signup and view all the answers

    What is the impact of introducing a polar group at the α-position of the side chain in penicillin G?

    <p>Confers activity against Gram-negative bacilli.</p> Signup and view all the answers

    What role does hydrophobicity play in the activity of antibiotics against Gram-positive and Gram-negative bacteria?

    <p>Hydrophobic chains improve Gram-positive activity but reduce Gram-negative activity.</p> Signup and view all the answers

    Which of the following statements about b-lactamases is true?

    <p>They can be transferred between bacterial strains.</p> Signup and view all the answers

    What is the primary role of penicillin in bacterial cell wall synthesis?

    <p>To inhibit the final crosslinking stage of cell wall synthesis</p> Signup and view all the answers

    What is formed when penicillin reacts with the transpeptidase enzyme?

    <p>An irreversible covalent bond</p> Signup and view all the answers

    What structural component does penicillin resemble to inhibit transpeptidase?

    <p>L-Ala-g-D-Glu portion of the pentapeptide chain</p> Signup and view all the answers

    What effect does the inhibition of transpeptidase have on bacterial cells?

    <p>Cells swell, then burst due to water influx</p> Signup and view all the answers

    What are the components involved in the bond formation during bacterial cell wall synthesis?

    <p>NAM, NAG, L-Ala, D-Glu, and L-Lys</p> Signup and view all the answers

    Which of the following statements is incorrect regarding penicillin's mechanism of action?

    <p>It enhances the integrity of the bacterial cell wall</p> Signup and view all the answers

    Which of the following amino acids is NOT directly involved in the process of bacterial cell wall synthesis?

    <p>L-Thr</p> Signup and view all the answers

    What happens to bacterial cells after the inhibition of the transpeptidase enzyme?

    <p>They experience cell lysis due to weakened walls</p> Signup and view all the answers

    What is the chemical nature of the bond that penicillin forms with the transpeptidase enzyme?

    <p>Covalent bond</p> Signup and view all the answers

    Which two sugars are fundamental components of the bacterial cell wall structure?

    <p>N-Acetylglucosamine and N-Acetylmuramic acid</p> Signup and view all the answers

    Study Notes

    Antibiotics

    • Antibiotics are substances produced by microorganisms that inhibit the growth or destruction of other microorganisms.
    • Waksman, in 1942, proposed a definition of antibiotics as substances produced by microorganisms capable of inhibiting the growth and destroying other microorganisms (e.g., bacteria, mycobacteria, fungi, protozoa, or viruses).
    • In 1947, Benedict and Langlykke defined antibiotics as chemical compounds derived from living organisms that inhibit life processes in microorganisms. This definition is broader, encompassing a wider range of sources including higher plants and mammals.
    • Modern antibiotics include naturally occurring compounds and those synthesized.

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    Description

    This quiz explores the definition, history, and classification of antibiotics, focusing on their origin and mechanisms of action. You will learn about early definitions proposed by scientists and the evolution of antibiotics from natural to synthetic compounds. Test your understanding of these crucial medicinal substances.

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