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Question 49

The structure shown below is of which well-known drug molecule?

image

The drug $$\mathrm{Cimetidine\ (Tagamet)}$$ was designed to prevent interaction of histamine with the receptors present in the stomach wall.

Cimetidine contains a modified imidazole ring similar to histamine.

Specifically, it contains a $$\mathrm{5\text{-}methylimidazole}$$ ring, which helps the molecule bind to the $$\mathrm{H_2}$$ receptor.

The side chain contains a sulfur atom, forming a $$\mathrm{Thioether}$$ linkage.

This longer chain helps the drug interact with additional binding sites on the receptor.

The most important structural modification is replacement of the strongly basic primary amine group of histamine with a $$\mathrm{Cyanoguanidine}$$ group.

Unlike the primary amine, the cyanoguanidine group remains largely neutral at physiological pH.

By this, Cimetidine binds strongly to the receptor without activating it and blocks the action of histamine.

Thus, D is the right option.

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