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Solutions For An Introduction to Medicinal Chemistry Chapter 19 Problem 9Q

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Solution 1

Any substance that is responsible for killing or inhibiting the growth of a microorganism is called as antimicrobial agents. It poses no harm to the host. These antimicrobials can be natural, synthetic or semi-synthetic. They are effective against the gram-positive as well as the gram-negative bacteria.

Bacampicillin is considered as the pro-drug of ampicillin. It is an ester called ethoxycarbonyloxyethyl eater. It can be converted to ampicillin on complete hydrolysis. There are many esterases present in the in the intestinal walls that are responsible for hydrolysis of becampicillin into ampicillin. The mechanism of conversion is shown as follows:

Figure: Mechanism of conversion of bacampicillin into ampicillin.

Ampicillin has a less bioavailability as compared to the bacampicillin. Therefore, the parent drug is produced by the pro-drug upon hydrolysis. The oral intake of ampicillin may cause diarrhea. Hence, it is produced on the absorption of becampicillin or pivampicillin. The byproducts produced are ethanol, carbon dioxide and water.

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Solutions For Problems in Chapter 19