Oversulfated chondroitin sulfate: impact of a heparin impurity, associated with adverse clinical events, on low-molecular-weight heparin preparation

J Med Chem. 2008 Sep 25;51(18):5498-501. doi: 10.1021/jm800785t.


Heparin, a widely used anticoagulant, is being rapidly displaced by low-molecular-weight heparins. Recently, certain lots of heparin have been associated with anaphylactoid-type reactions resulting from contamination with oversulfated chondroitin sulfate. This impurity has also contaminated low-molecular-weight heparins obtained by chemical and enzymatic depolymerization of heparin. The sensitivity of oversulfated chondroitin sulfate to five different depolymerization processes similar to ones used in preparing low-molecular-weight heparins is reported.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anticoagulants / adverse effects
  • Anticoagulants / chemistry*
  • Chondroitin Sulfates / adverse effects*
  • Chondroitin Sulfates / isolation & purification*
  • Heparin, Low-Molecular-Weight / adverse effects
  • Heparin, Low-Molecular-Weight / chemistry*
  • Magnetic Resonance Spectroscopy
  • Polymers


  • Anticoagulants
  • Heparin, Low-Molecular-Weight
  • Polymers
  • Chondroitin Sulfates