L23 - Metabolism And Drug Synthesis
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What is salbutamol?
B2 agonist - used to treat COPD - Chronic obstructive pulmonary disease
What are the steps in the synthesis of salbutamol?
• formation of an ester • friedel crafts acylation • enol as nucleophile • immine via condensation reaction • reduction
How does the formation of an ester occur for the formation of salbutamol?
Salicylic acid + EtOH, Acid = Ester
How does Friedel Crafts acylation occur for the formation of salbutamol?
Methyl salicylate + acyl chloride = desired product - methyl salicylate + ketone at the para,meta position
How does enol as a nucleophile occur for the formation of salbutamol?
Desired product + Br2 (via enol) = Br extensino to ketone
How does immine via condensation reaction occur for the formation of salbutamol?
+ NH2 (Sn2) - lp on N attacks C on C-Br
How does reduction occur for the formation of salbutamol?
LiAlH4, Et2O - ketone becomes secondary alcohol
What is the active enantiomer of salbutamol?
R
What is pharmacokinetics and the 4 areas?
The study of what the body does to a drug - absorption - distribution - metabolism - excretion
What is drug metabolism?
The chemical process to conert drugs into compounds that are easier to eliminate
What do metabolic enzymes make drugs in general?
More polar - Drug (lipophilic) -> metabolite (hydrophilic)
Where does most drug metabolism occur?
In the liver
What is phase 1?
• oxidation • reduction • hydrolysis
What is phase 2?
Make drug (conjugates/metabolite) conjugates Attach ionised group to increase polarity/aid excretion
What are examples of ionised groups that increase polarity/aid excretion?
• methyl • acetyl • glucoronidation • amino acids • glutathione