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Solutions For An Introduction to Medicinal Chemistry Chapter 10 Problem 1Q

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Solution 1

Cyclodextrins are macrocyclic structures made up of carbohydrate building blocks. The interior of the cyclodextrins is relatively hydrophobic and can accommodate drug-sized molecules. Sugammadex is a cyclodextrin, which is designed to scavenge rocuronium, a steroidal neuromuscular agent.

Cyclodextrin scavenges this rocuronium to reduce its lifetime in the blood supply and thus it help for those patients who have undergone surgery by quicker recovery time. Carboxylate group in the sugammadex has an important role in allowing the drug access to the central cavity due to the following reasons:

1. Sugammadex consists of eight identical carbohydrate molecules, in which the hydroxyl and the carboxylate groups interact with water, which makes it water soluble.

2. The face of the carbohydrate rings forms the interior of the macrocyclic structure and thus becomes hydrophobic in nature.

3. Quaternary ammonium ions of the drug form an ionic interaction with the carboxylate group of the sugammadex and help in locking of the steroid into the cyclodextrins.

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