Synthesis and physicochemical properties of sulfamate derivatives as topical antiglaucoma agents

J Med Chem. 1992 Dec 25;35(26):4790-4. doi: 10.1021/jm00104a003.


Several imidazolylphenyl sulfamate and (imidazolylphenoxy)alkyl sulfamate derivatives were synthesized and evaluated as topically active carbonic anhydrase inhibitors. Water solubility, pKa, carbonic anhydrase inhibition, and partition coefficient for the compounds were measured. Sulfamic acid 2-[4-(1H-imidazol-1-yl)phenoxy]ethyl ester monohydrochloride (16) has the best combination of properties and showed excellent topical activity in lowering the intraocular pressure in New Zealand white rabbits.

MeSH terms

  • Administration, Topical
  • Animals
  • Carbonic Anhydrase Inhibitors / chemical synthesis*
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / therapeutic use
  • Glaucoma / drug therapy*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / therapeutic use
  • Intraocular Pressure / drug effects
  • Rabbits
  • Structure-Activity Relationship
  • Sulfonic Acids / chemical synthesis*
  • Sulfonic Acids / chemistry
  • Sulfonic Acids / pharmacology


  • Carbonic Anhydrase Inhibitors
  • Imidazoles
  • Sulfonic Acids