Wednesday, September 14, 2011

Enantiomer in Thalidomide Causes Birth Defects

http://pubs.acs.org/cen/coverstory/83/8325/8325thalidomide.html

Thalidomide was a drug used from 1957 to 1961 to reduce nausea and insomnia in pregnant women. It was later discovered that women who took this medication during pregnancy were giving birth to babies with severe deformities. Now, there is clinical interest in the drug for treatment in conditions such as leprosy due to its anti-inflammatory effects. Female patients who are prescribed thalidomide are frequently tested for pregnancy while using the drug. It also has antiangiogenic and immunomodulatory properties  that can be effective against certain cancers, such as multiple myeloma. 

                                                 The Enantiomers of Thalidomide


Thalidomide had been available as a racemate, which has both "left and right-handed" enantiomers of the molecule. Enantiomers may have very different biological functions, but in thalidomide, the enantiomers undergo "rapid chiral inversion". Thus, even if only the "good" enantiomer was present, it would have converted to the "bad" enantiomer, still resulting in birth defects.



      A Birth Defect Caused by Thalidomide

2 comments:

  1. Thalidomide is known to be a powerful teratogenic drug, which causes serious abnormal embryo or fetal development. Even one dose of thalidomide during pregnancy can cause major thalidomide birth defects.

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