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Chemistry

How Chirality Influences the Pharmacokinetics of Thalidomide Analogues

Quick fact

Even though the (R)-enantiomer of thalidomide is responsible for the sedative effects while the (S)-enantiomer is teratogenic, the drug rapidly racemizes in the body, so the harmful form is always present. Moreover, the body can metabolize each enantiomer differently, altering their pharmacokinetic profiles and toxicity.

Why this is interesting

Imagine a drug that is safe for one hand but toxic for the other—yet you cannot separate them. That is the challenge of chiral drugs like thalidomide: its two mirror-image forms behave differently in the body, and they even convert into each other. How does this chemical subtlety influence how the drug is absorbed, distributed, metabolized, and excreted?