Thalidomide
Background
Thalidomide has long been known as an example of a drug "gone bad". Originally prescribed as a sedative in the late 1950's, it was later found to cause birth defects. Approximately 12,000 children were born with some form of defect due to damage caused by this drug. Approval of this drug was quickly revoked.
Today, researchers are again interested in thalidomide and derivatives as a treatment to reduce inflammation in patients with leprosy, to treat tumors in cancer patients, and in treatment of HIV. For more information on Thalidomide, see the University of Bristol's Molecule of the Month web site.
Thalidomide is an optically active molecule with one stereogenic center. It is believed that the "S" form is therapeutically beneficial while the "R" form can cause undesirable side effects. Unfortunately, in solution, the two forms interconvert, so a racemic mixture is obtained. Current research efforts focus on synthesis of similar compounds where this interconversion is hindered.
 |
 |
| "R" isomer | "S" isomer |