[Campbell Biology P.114] Thalidomide is a drug whose beneficial enantiomer can be synthesize... | Practice Question

Thalidomide is a drug whose beneficial enantiomer can be synthesized and administered, but over time, both the beneficial and harmful enantiomers are detected in the body. Which of the following is the most plausible explanation for the presence of the harmful enantiomer in a patient's body?

  • A: The beneficial enantiomer undergoes spontaneous racemization into the harmful form in the body.
  • B: The body metabolizes the beneficial enantiomer into a new harmful compound, which is also an enantiomer.
  • C: The patient consumes the harmful enantiomer unknowingly through their diet.
  • D: The drug formulation initially contains a small amount of the harmful enantiomer as an impurity.

Explanation

The most plausible explanation for the detection of the harmful enantiomer after administering only the beneficial one is that the beneficial enantiomer undergoes racemization within the body. This is a known characteristic of thalidomide, where it can interconvert between its enantiomeric forms under physiological conditions.