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Solutions For An Introduction to Medicinal Chemistry Chapter 14 Problem 2Q

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Solution 1

Penicillin is a group of antibiotics, which include different types of penicillin such as benzathine penicillin, penicillin V, penicillin G, and procaine penicillin. Each of the types has different targets in the body. Penicillin is one of the first antibiotics used to treat bacterial infections. They are very effective however; many bacteria species have developed resistance to it.

Penicillin contains a β-lactam (beta lactam) ring, which has certain amino groups in it. Penicillin gets easily degraded in a concentrated aqueous solution. This happens because of the intramolecular attack of the amino groups located in the side chain of the β-lactam ring.

The β-lactam ring has nitrogen, which is blocked when the drug hetacillin is added to the aqueous solution. Hetacillin is a prodrug. Hetacillin, then slowly decomposes into two products, ampicillin and acetone. Thus, the ampicillin can be taken up and absorbed by the target.

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Solutions For Problems in Chapter 14