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Solutions For An Introduction to Medicinal Chemistry Chapter 14 Problem 1Q

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Solution 1

Methenamine is a prodrug, which is found in stable and inactive form in the body. It decomposes slowly at an acidic pH producing formaldehyde, which is toxic to most of the bacteria. Methenamine acts as an anti- infective agent. It is stable and inactive at pH range of 5-6. It degrades in stomach due to acidic environment of the stomach. It becomes active after the degradation and is responsible for mechanism of action in urine.

In the acidic environment, Methenamine is converted into antibacterial agent known as formaldehyde. The requirement of pH range for this conversion is less than 5. Normally Methenamine is formulated in a pill form which protects it from the high alkaline environment. This pill then dissolves in acidic medium and gets converted into formaldehyde.

This reaction is usually done for preventing urinary infections. The product of the reaction that is formaldehyde kills the bacteria of the urine and urinary tract. Thus, maintain a bacteria free environment in the urinary tract.

Figure: Reaction showing the conversion of Methenamine to formaldehyde.

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Solutions For Problems in Chapter 14