Fundamentals of Medicinal Chemistry

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A.5 Transfer through membranes


Substances are transported through membranes by osmosis, filtration, passive

diffusion, facilitated diffusion, active transport, endocytosis and exocytosis.

Passive diffusionis the major route for the transport of drugs across membranes.

It occurs down a concentration gradient from a high to a low concentration. In

passive diffusion the drug dissolves into the lipid membrane from the aqueous

medium, diffuses across the membrane and dissolves out of the membrane into

the aqueous medium. Since the interiors of membranes are nonpolar, passive

diffusion is most effective for uncharged nonpolar species. Charged and highly

polar species are not easily transported through a membrane by passive diffu-

sion. However, a potential drug must have sufficient polar character to pene-

trate the hydrophilic surface of the membrane. Consequently, the structures of

potential drugs must contain a balanced ratio of lipid solubilizing regions to

water solubilizing regions if a sufficient concentration of the compound is to

cross a membrane by passive diffusion.

Active transport is also an important route for the transfer of drugs through a

membrane by a so calledcarrier protein. The solute combines with a specific

protein in the membrane, causing this protein to change its conformation. This

change results in the transport of the solute from one side of the membrane to the

other, where it is released into the aqueous medium. The rate of active transport is

dependenton the concentration of the solute at the absorption sites. It follows first

order kinetics at concentrations less than those required to saturate the available

carriers but changes to zero order at concentrations above the saturation point.

Consequently, increasing a drug’s concentration above the saturation limit in the

extracellular fluid does not increase the rate at which the drug is delivered to its

active site. Active transport usually operates from a low concentration to a high

concentration, which requires the cell to expend large quantities of energy.

Carrier proteins are highly selective, transporting solutes with specific chemical

structures. As they are normally involved in the transport of many naturally

occurring compounds they will often transport drugs with structures related to

these natural products. This type of structural relationship can be use in the

approach to the design of new drugs.

Facilated diffusion also involves the use of a carrier protein. It differs from

active transport in that it occurs from a high to a low concentration and so does

not require energy to be supplied by the cell. However, falicilated diffusion

appears to play a minor role in the transport of drugs through membranes.

APPENDIX 5 TRANSFER THROUGH MEMBRANES 249

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