L23 - Application of Lectures in Drug Synthesis

• What is salbutamol?


  beta 2 agonist (bronchodilator) used for asthma/COPD

  
• How is an ester formed?

  
  

  (eg salbutamol synthesis)

  carboxylic acid, alcohol, acid catalyst

  
  

  (Eg salicylic acid + ethanol)

  
• How can an acyl group be added?

  Friedel-Crafts Acylation:

  
  

  AlCl3 (Lewis Acid catalyst) reacts with acyl chloride to form an electrohile, which can then attack aromatic ring

  
• What is drug metabolism?

  - chemical process to convert drug molecules into compounds that are easier to convert/excrete
• Where does drug metabolism mainly occur?

  
  

  What does it do to drugs?

  - liver

  
  

  - makes drugs more polar (drugs are normally lipophilic to aid absorption)
• What happens in phase 1 metabolism?

  
  

  What reagents are used to undertake these?

  Oxidation - cytochrome P450

  
  

  Reduction - NADPH

  
  

  Hydrolysis
• What's involved in phase 2 metabolism?

  Enzymatic conjugation reactions to turn drug into drug-conjugates or metabolite-conjugates
• What is conjugation?


  attachment of an ionic group to a drug/metabolite to increase polarity