Chiral Inversion of the Second Generation IMiD CC-4047 (ACTIMID ) in Human Plasma and Phosphate-Buffered Saline

Chirality. 2003 May 5;15(4):348-51. doi: 10.1002/chir.10221.


CC-4047 is a racemic second-generation immunomodulatory drug currently in clinical development for various oncologic indications. It has potent effects on key cytokines including tumor necrosis factor-alpha, interleukin (IL-10), and interferon (IFN-gamma). The S-isomer of CC-4047 has been reported to be the more potent enantiomer of the racemate. In this article we report on the rapid racemization of the S-isomer of CC-4047 in human plasma and phosphate-buffered saline. These results support the further development of the racemate instead of the S-isomer.

MeSH terms

  • Adjuvants, Immunologic / blood*
  • Adjuvants, Immunologic / chemistry*
  • Adjuvants, Immunologic / pharmacokinetics
  • Antineoplastic Agents / blood
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics
  • Humans
  • In Vitro Techniques
  • Neoplasms / drug therapy
  • Sodium Chloride
  • Stereoisomerism
  • Thalidomide / analogs & derivatives
  • Thalidomide / blood*
  • Thalidomide / chemistry*
  • Thalidomide / pharmacokinetics


  • Adjuvants, Immunologic
  • Antineoplastic Agents
  • Sodium Chloride
  • Thalidomide
  • pomalidomide