Top Document: Sci.chem FAQ - Part 6 of 7 Previous Document: 27. Fuel Chemistry Next Document: 29. Adhesive Chemistry See reader questions & answers on this topic! - Help others by sharing your knowledge 28.1 Does Thalidomide racemise in humans?. Thalidomide ( N-phthaloyl-alpha-aminoglutarimide ) is well known as an enantiomeric sedative-hypnotic drug that caused tragic birth defects in the early 1960s. It has often been claimed that the defects were caused by the presence of the other isomer in the production batches, and if the pure enantiomer had been sold, then the tragic defects would have been avoided. Unfortunately, thalidomide is optically unstable in solution; the pure isomers of thalidomide racemise by the opening of the phthalimide ring, with half-lives of 4-5 hours in buffer at pH 7.4, and less than 10 minutes in the blood. Thus shortly after administration of either enantiomer, the other enantiomer will be present in significant quantities [1]. Some recent work has revealed that thalidomide inhibits the production of tumour necrosis factor alpha. Elevated levels of TNF-alpha are associated with several inflammatory conditions. This has led to the development of analogues that are chirally stable in reconstituted human plasma, and which are undergoing development as anti-inflammatory drugs [2]. User Contributions:Top Document: Sci.chem FAQ - Part 6 of 7 Previous Document: 27. Fuel Chemistry Next Document: 29. Adhesive Chemistry Part1 - Part2 - Part3 - Part4 - Part5 - Part6 - Part7 - Single Page [ Usenet FAQs | Web FAQs | Documents | RFC Index ] Send corrections/additions to the FAQ Maintainer: B.Hamilton@irl.cri.nz
Last Update March 27 2014 @ 02:12 PM
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