Carbonic anhydrase inhibitors: topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide.
Article Details
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Casini A, Scozzafava A, Mincione F, Menabuoni L, Starnotti M, Supuran CT
Carbonic anhydrase inhibitors: topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide.
Bioorg Med Chem Lett. 2003 Sep 1;13(17):2867-73.
- PubMed ID
- 14611846 [ View in PubMed]
- Abstract
Reaction of 3- and 4-carboxybenzenesulfonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulfonamide/5-imino-4-methyl-delta(2)-1,3,4-thiadiazo line-2-sulfonamide afforded two series of benzolamide analogues to which the carboxyl moiety has been derivatized as esters or amides, in order to reduce their very polar character. The new derivatives showed low nanomolar affinity for three carbonic anhydrase (CA) isozymes, CA I, II and IV, and were effective as topical antiglaucoma agents in normotensive rabbits. Efficacy of several of the new sulfonamides reported was better than that of the standard drugs dorzolamide and brinzolamide, whereas their duration of action was prolonged as compared to that of the clinically used drugs.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) 5-[(phenylsulfonyl)amino]-1,3,4-thiadiazole-2-sulfonamide Carbonic anhydrase 2 Ki (nM) 9 N/A N/A Details Acetazolamide Carbonic anhydrase 1 Ki (nM) 200 N/A N/A Details Acetazolamide Carbonic anhydrase 2 Ki (nM) 7 N/A N/A Details Brinzolamide Carbonic anhydrase 2 Ki (nM) 3 N/A N/A Details Dorzolamide Carbonic anhydrase 1 Ki (nM) 50000 N/A N/A Details Dorzolamide Carbonic anhydrase 2 Ki (nM) 9 N/A N/A Details Ethoxzolamide Carbonic anhydrase 1 Ki (nM) 25 N/A N/A Details Ethoxzolamide Carbonic anhydrase 2 Ki (nM) 8 N/A N/A Details