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Isomerism

Stereochemistry, drug action and receptor sites

  • 3 things to know
  • Unit A2 1

Overview

Recall questions on what makes a receptor site stereospecific, why activity depends on which enantiomer is used, why the inactive one is not always harmless, thalidomide and why supplying one enantiomer would not have helped, why an ordinary synthesis gives a racemate, chiral catalysts, and both sides of the regulatory argument.

What you need to know

Answer each one before you reveal it.

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Key term

What is a stereospecific receptor site, how do the enantiomers of a chiral drug usually differ, and what did thalidomide show?

Key term

Explain what is meant by a stereospecific receptor site.

Key term

Explain why the activity of a drug can depend on which enantiomer is used.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Explain what is meant by a stereospecific receptor site.

    Model answer

    A stereospecific receptor site has a shape that accepts only one particular three-dimensional arrangement of a molecule and rejects its mirror image.

  2. 2

    Explain why the activity of a drug can depend on which enantiomer is used.

    Model answer

    The receptor site in the body is itself chiral, so only the enantiomer with the matching arrangement of groups can bind to it and produce the intended effect.

  3. 3

    Describe the most common relationship between the two enantiomers of a chiral drug.

    Model answer

    One enantiomer usually produces the desired therapeutic effect while the other is much less active or entirely inactive.

  4. 4

    Explain why the inactive enantiomer in a racemic drug is not always harmless.

    Model answer

    The other enantiomer may fit a different receptor and cause unwanted side effects or toxicity rather than simply doing nothing.

  5. 5

    Name the drug whose two enantiomers had drastically different biological effects and describe them.

    Model answer

    Thalidomide has one enantiomer that acts as a sedative and another that causes severe damage to a developing fetus.

  6. 6

    Explain why supplying only the safe enantiomer of thalidomide would not have solved the problem.

    Model answer

    The two forms interconvert in the body, so a pure single enantiomer would still produce a mixture once it had been taken.

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