Fundamentals of Medicinal Chemistry

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orally administered drugs. Most orally administered drugs are absorbed

through the membranes of the GI tract. The rate of absorption will depend

mainly on the rate of dissolution of the dosage form, that is, the rate at which

the drug solid dosage forms passes into solution, the pH of the medium con-

taining the drug (see Section 2.7.1), the lipid–aqueous medium partition coeffi-

cient of the drug and the surface area of the absorbing region of the GI tract.

Drugs absorbed from the GI tract must pass through the GI tract membrane,

liver and other organs in order to reach the general circulation system. A

fraction of the drug will be lost by metabolism and excretion as it follows this

route to the circulatory system. These losses are referred to as thefirst pass effect

orfirst pass metabolism. Since the main areas of excretion and metabolism in the

systematic circulatory system are the enzyme-rich liver and lungs, the term is

usually taken to refer to the elimination of a drug by these two organs. However,

since the liver is the first organ the drug passes through after absorption from

the GI tract and it is also the principal area of metabolism, the effect of the lungs

is often ignored, and the term first pass metabolism is frequently used as though

it involved only the liver.

The physiology of drug absorption from the GI tract has a direct effect on the

bioavailability(F) of a drug. Bioavailability is defined as the fraction of the dose

of a drug that enters the general circulatory system, that is:


amount of drug that enters the general circulatory system

dose administered

(8:22)

Since the area under the plasma concentration–time curve (AUC) for a drug

is a measure of the total amount of a drug reaching the general circulatory

system, the bioavailability of a drug may also be defined in terms of the AUC

as:

F¼AUC=dose (8:23)

If all the dose of a drug reached the circulatory system, the bioavailability as

defined by Equation (8.22) would have a value of unity 1. Therefore, ifEis the

extraction for first pass metabolism,

F¼ 1 E (8:24)

and so, for orally administered drugs, Equation (8.24) approximates to:

F¼ 1 EH (8:25)

172 PHARMACOKINETICS

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