Biopharmaceutical explanation for the topical activity of 6-hydroxyethoxy-2-benzothiazolesulfonamide in the rabbit eye

J Ocul Pharmacol. 1992 Fall;8(3):247-65. doi: 10.1089/jop.1992.8.247.

Abstract

6-Hydroxyethoxy-2-benzothiazolesulfonamide (compound 1), 6-hydrogen-2-benzothiazolesulfonamide (compound 2) and ethoxzolamide (compound 3) are carbonic anhydrase inhibitors, of which only compound 1 is active in lowering intraocular pressure when administered to the rabbit eye. They were compared for potency by inhibiting carbonic anhydrase I (CAase I) using the pH stat procedure. No differences were detected. Binding affinity and number of binding sites were identical; only a single binding site was operative. 14C-labelled compound 1 was used to measure the presence of an ocular metabolite which ranged from 17 to 57% in cornea, iris/ciliary body and aqueous humor. By maintaining drug solutions on either the corneal or conjunctival/scleral surfaces of the eye of anesthetized rabbits for 120 minutes, steady state concentrations of compounds 1-3 were determined in cornea, aqueous humor and iris/ciliary body. It was concluded that compound 1 penetrated both routes equally well and also accumulated at the active site in considerably higher concentrations than compounds 2 and 3. Compounds 2 and 3 did not accumulate in the iris/ciliary body nor did compound 3 penetrate the conjunctival/scleral route very well, approximately 5-20 fold lower than from the corneal route.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Topical
  • Animals
  • Benzothiazoles
  • Carbonic Anhydrase Inhibitors / pharmacokinetics*
  • Chromatography, High Pressure Liquid
  • Ethoxzolamide / analogs & derivatives*
  • Ethoxzolamide / pharmacokinetics
  • Eye / metabolism*
  • Female
  • Male
  • Protein Binding
  • Rabbits
  • Sulfonamides / pharmacokinetics
  • Thiazoles / pharmacokinetics
  • Tissue Distribution

Substances

  • Benzothiazoles
  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Thiazoles
  • 2-benzothiazolesulfonamide
  • 6-hydroxyethoxzolamide
  • Ethoxzolamide