Synthesis and physicochemical properties of sulfamate derivatives as topical antiglaucoma agents.
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.
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A.H. Robins Company, Richmond, Virginia 23261-6609.
Nolan
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JC
Maren
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Welstead
W J
WJ
Gripshover
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Shamblee
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D000287:Administration, Topical; D000818:Animals; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D005901:Glaucoma / Q000188:drug therapy*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D007429:Intraocular Pressure / Q000187:drug effects; D011817:Rabbits; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D002257:Carbonic Anhydrase Inhibitors; D007093:Imidazoles; D013451:Sulfonic Acids