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19 Cards in this Set

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What are the 3 subclasses of ACE inhibitors?
Sulfhydryl
Dicarboxylate
Phosphonate
Name the representative drug for each subclass and its distinct structural characteristic
Sulfhydryl - Captopril - Sulfur group
Dicarboxylate - Enalapril - Ester group
Phosphonate - Fosinopril - Phosphate
The Sulfhydryl group in Captopril is important for ACE inhibition, but also produces 2 side effects. What are they?
Skin Rash
Taste Disturbance
In the development of Enalapril (Dicarboxylate), what was the goal?
Develop a compound that lacked the sulfhydryl group of Captopril
Why is Enalapril needed orally?
Enapril is the prodrug of Enaprilate.
Enapril is esterified and doesn't form the zwitterion with the secondary amine which decreases intestinal uptake. Esterases convert Enapril (OCH3) to Enaprilate (OH) to carry out ACE inhibitory function.
What is the other important Dicarboxylate ACE inhibitor to know?
Lisinopril
What are the only 2 ACE inhibitors that are not prodrugs?
Captopril and Lisinopril
Sulfhydryl groups can form dimers. What effect would this have on the drug action?
It would shorten the duration of action.
How you get an orally available prodrug?
By esterifying the carboxylate or phosphonate group.
Captopril and Fosinopril are what type of drugs?
Acidic drugs
All other ACE inhibitors are amphoteric
In Enalapril, the amine group is adjacent to an ester. What effect does this have on the molecule?
It makes it less basic and primarily unionized at physiological pH.
When the amine group is next to a carboxylic acid, it is more basic and more readily ionizable.
What feature of ACE inhibitors make them more lipophilic?
Hydrophobic bicyclic rings more so than proline.
Lisinopril is the most hydrophilic of the ACE inhibitors. However, unlike Enalaprilate, it is orally active. Why is this?
In forms a di-zwitterion in the duodenum so the ion groups internally bind. The molecule can pass through the lipid bilayer with a net neutral charge.
Describe the metabolism of Lisinopril and Enalapril.
They are excreted unchanged.
How are all other ACE inhibitors altered to be excreted?
Via hepatic esterases
How is Captopril metabolized?
It dimerizes or is conjugated
What is the most widespread Angiotensin antagonist? How do these drugs work?
Losartan
They block the active site on the angiotensin receptor.
Eprosartan is another Angiotensin antagonist. How does it work?
It mimics the C-terminal end of angiotensin II.
Losartan is metabolized to another compound which is an angiotensin antagonist. What is this compound?
EXP-3174
Much better inhibitor than Losartan
Occurs via CYP 2C9