Entropy depicts distribution or partitioning of a localized surface energy noted as potential energy partitioned in different patterns within the giant molecules like intramolecular hydrogen bonding. Energy partition is calculated using Boltzmann energy concept as S = kB ln W, S entropy, kb Boltzmann constant, W partitioning factor.
I don't follow the body of your question, but in response to the title. The interaction of a dendrimer with a drug may cause confinement of the drug within the dendrimer, forcing it into a smaller number of conformations, therefore inducing an entropic penalty. And the dendrimer is less able to move while interacting with the drug, also giving an entropic penalty.
There are also likely to be solvent effects, for example if water is displaced from the dendrimer by the drug, into the bulk solvent, this might well be entropically favourable.
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