The drug Ramiprilat is an ACE inhibitor and is therefore used in the treatment o

Question

The drug Ramiprilat is an ACE inhibitor and is therefore used in the treatment ot high blood pressure. Based on your knowledge of log P values (1.5) as well as on Ramiprilat's chemcial structure, would you expect the compound to have good or poor oral bioavailablity? Explain. At physiological pH (7.4) would you expect Ramiprilat to be in its neutral or ionized form? Explain. Ramiprilat is known to have a very short duration of action and as such it needs to be frequently administered. One method of allowing for a more prolonged duration of action is to administer the drug as a Prodrug .which is converted in vivo to the active Ramiprilat. Suggest a structure of a potential prodrug along with a reaction to synthesize it and explain why your compound would allow for a slower and longer duration of action for the drug.

Explanation / Answer

(a): With a log P value or (octanol/water partition) coefficient value of 1.5, the oral bioavailability percentage will be less than 50 %. Hence it should have a poor oral bioavailability value.

(b): Since the pKa value of ramiprilat is around 3.2 which is less than 7.4. Hence at physiological pH value of 7.4, ramiprilat will be in neutral form.

(c):

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