Abstract
Soon after the discovery of carbonic anhydrase (CA) (Meldrum and Roughton, 1932) it was shown by Mann and Keilin (1940) that certain sulfonamides were specific and potent inhibitors of this enzyme. Since then various arene-and heteroarene-sulfonamides have been synthesised and evaluated (Maren, 1967, 1974) as inhibitors of carbonic anhydrase for possible therapeutic use as anticonvulsants (Gray et al., 1957; Gray and Rauh, 1967), antiglaucoma agents (Becker, 1954; Friedenwald, 1949), cerebral vasodilators (Barnish et al., 1980; Cross et al., 1978), and diuretics Peters and Roch-Ramel, 1969).
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References
Antonaroli S, Bianco A, Brufani M, Cellai L, Lo Baido G, Potier E, Bonomi L, Perfetti S, Fiaschi AI, Segro G (1992) Acetazolamide-like carbonic anhydrase inhibitors with topical ocular hypotensive activity. J Med Chem 35: 2697–2703
Baird TT, Waheed A, Okuyama T, Sly W S, Fierke CA (1997) Catalysis and inhibition of human carbonic anhydrase IV. Biochemistry 36: 2669–2678
Baldwin JJ, Ponticello GS, Anderson PS, Christy ME, Murcko MA, Randall WC, Schwam H, Sugrue MF, Springer JP, Gautheron P, Grove J, Mallorga P, Viader M-P, McKeever BM, Navia MA (1989) Thienothiopyran-2-sulfonamides: Novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma. J Med Chem 32: 2510–2513
Barnish IT, Cross PE, Dickinson RP, Gadsby B, Parry MJ, Randall MJ, Sinclair IW (1980) Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 2. Imidazo[2,1-b]thiadiazole and imidazo[2,1-b]thiazolesulfonamides. J Med Chem 23: 117–121
Becker B (1954) Decrease in intraocular pressure in man by a carbonic anhydrase inhibitor, Diamox. Am J Ophthalmol 37: 13–15
Blackburn GM, Lilley TH, Milburn PJ (1984) Aqueous-solutions containing amino-acids and peptides. 19. The enthalpic coefficients for the interactions of N-acetylsarcosinamide with 2-(N-acetylamino)acyl amides at 25°C. J Solution Chem 13: 789–803
Blackburn GM, Lilley TH, Milburn PJ (1985) Aqueous-solutions containing amino-acids and peptides. 16. Solute solute interactions in solutions containing some N-acetyl-N´-methylamino acid-amides. J Chem Soc Faraday Trans 181: 2191–2205
Blackburn GM, Lilley TH, Milburn PJ (1985) Aqueous-solutions containing amino-acids and peptides. 21. The enthalpic coefficients at 298.15-K for the interaction of Nacetyl-L-prolinamide with some 2-(N-acetylamino) acylamides. Thermochimica Acta 289–297
Blackburn GM, Mann BE, Taylor BF, Worrall AF (1985) A nuclear-magnetic-resonance study of the binding of novel N-hydroxybenzenesulfonamide carbonic anhydrase inhibitors to native cadmium-III-substituted carbonic anhydrase. Eur J Biochem 153: 553–558
Blackburn GM, Trager SF, Zhang X-R (2000) J Med Chem in preparation
Boriack PA, Christianson DW, Kingery-Wood J, Whitesides GM (1995) Secondary interactions significantly removed from the sulfonamide binding pocket of carbonic anhydrase II influence inhibitor binding constants. J Med Chem 38: 2286–2291
Boriack-Sjodin PA, Heck RW, Laipis PJ, Silverman DN, Christianson DW (1995) Structure determination of murine mitochondrial carbonic anhydrase V at 2.45-Å resolution: Implications for catalytic proton transfer and inhibitor design. Proc Nati Acad Sci USA 92: 10949–10953
Borras J, Cristea T, Supuran CT (1996) Complexes with biologically-active ligands. 5. Zn(II) and Cd(II) coordination-compounds of hydrazine and heterocyclic sulfonamides as inhibitors of the zinc enzyme carbonic anhydrase. Main Group Metal Chem 19: 339–345
Brechue WF, Maren TH (1993) Carbonic anhydrase inhibitory activity and ocular pharmacology of organic sulfamates. J Pharmacol Exp Ther 264: 670–675
Brezeanu M, Olar R, Meghea A, Stanica N, Supuran CT (1996) 1,3,4-Thiadiazole derivatives. 5. Heteropolynuclear complexes of 2-amino-5-mercapto-1,3,4-thiadiazole. Rev Roum Chim 41: 103–107
Brezeanu M, Olar R, Supuran CT, Stanica N, Stoicescu M (1996) 1,3,4-Thiadiazole derivatives. 6. Polynuclear complexes of 2-amino-5-mercapto-1,3,4-thiadiazole with Co(II) and Ni(II). Rev Roum Chim 41: 681–685
Cappalonga Bunn AM, Alexander RS, Christianson DW (1994) Mapping protein-peptide affinity: Binding peptidylsulfonamide inhibitors to human carbonic anhydrase II. J Am Chem Soc 116: 5063–5068
Chen RF, Kernohan JC (1967) Combination of bovine carbonic anhydrase with a fluorescent sulfonamide. J Biol Chem 242: 5813–5823
Coleman JE (1975) Chemical reactions of sulfonamides with carbonic anhydrase. Ann Rev Pharmacol 15: 221–242
Colucci DF, Buyske PA (1965) The biotransformation of a sulfonamide to a mercaptan and to mercapturic acid and glucuronide conjugates. Biochem Pharmacol 14: 457–466
Conroy CW, Schwam H, Maren TH (1984) The nonenzymatic displacement of the sulfamoyl group from different classes of aromatic compounds by glutathione and cysteine. Drug Metab Dispos 12: 614–618
Cross PE, Gadsby B, Holland GF, McLamore WM (1978) Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 1. Substituted benzenesulfonamides. J Med Chem 21: 845–850
Debenedetti PG, Iarossi D, Menziani MC, Frasinetti C, Benedetti A (1988) Multinuclear NMR and vibrational spectroscopy studies of the substituent effects in benzenesulfonamide inhibitors of the enzyme carbonic anhydrase. J Mol Structure 175: 37–42
Diestelhorst M, Béchetoille A, Lippa EA, Brunner-Ferber F, Krieglstein GK (1989) Invest Ophthalmol Visual Sci 30: 23
Dugad LB, Gerig JT (1988) NMR-studies of carbonic anhydrase-4-fluorobenzenesulfonamide complexes. Biochemistry 27: 4310–4316
Dugad LB, Cooley CR, Gerig JT (1989) NMR-studies of carbonic anhydrase-fluorinated benzenesulfonamide complexes. Biochemistry 28: 3955–3960
Eller MG, Schoenwald RD, Dixson JA, Segarra T, Barfknecht CF (1985) Topical carbonicanhydrase inhibitors. 3. Optimization model for corneal penetration of ethoxzolamide analogs. J Pharm Sci 74, 2: 155–160
Engstrand C, Jonsson B-H, Lindskog S (1995) Catalytic and inhibitor-binding properties of some active-site mutants of human carbonic-anhydrase-I. Eur JBiochem 229: 696–702
Epstein DL, Grant WM (1977) Arch Ophthalmol 95: 1378–1382
Eriksson AE, Kylsten PM, Jones TA, Liljas A (1988) Crystallographic studies of inhibitor binding sites in human carbonic anhydrase II: A pentacoordinated binding of SCN– ion to the zinc at high pH. Proteins, Structure, Function and Genetics 4: 283–293
Foss RH (1955) Local application of Diamox: An experimental study of its effect on the intraocular pressure. Am J Ophthalmol 39: 336–339
Friedenwald JS (1949) The formation of the intraocular fluid. Am J Ophthalmol 32: 9–27
Gao J, Qiao S, Whitesides GM (1995) Increasing binding constants of ligands to carbonic anhydrase by using “greasy tails”. J Med Chem 38: 2292–2301
Graham SL, Hoffman JM, Gautheron P, Michelson SR, Scholz TH, Schwam H, Shepard KL, Smith AM, Smith RL, Sondey JM et al. (1990) Topically active carbonic anhydrase inhibitors. 3. Benzofuran-and indole-2-sulfonamides. J Med Chem 33: 749–754
Graham SL, Shepard KL, Anderson PS, Baldwin JJ, Best DB, Christy ME, Freedman MB, Gautheron P, Habecker CN, Hoffman JM et al (1989) Topically active carbonic anhydrase inhibitors. 2. Benzo[b]thiophenesulfonamide derivatives with ocular hypotensive activity. J Med Chem 32: 2548–2554
Gray WD, Rauh CE (1967) The anticonvulsant action of inhibitors of carbonic anhydrase; site and mode of action in rats and mice. J Pharmacol Exp Ther 156: 383–396
Gray WD, Maren TH, Sisson GM, Smith FH (1957) Carbonic anhydrase inhibition (VII) Carbonic anhydrase inhibition and anticonvulsant effect. J Pharmacol Exp Ther 121: 160
Hageman GS, Zhu XL, Waheed A, Sly WS (1991) Localization of carbonic anhydrase IV in a specific capillary bed of the human eye. Proc Natl Acad Sci USA 88: 216–220
Hansch C, McClarin J, Klein TE, Langridge RA (1985) Quantitative structure-activity relationship and molecular graphics study of carbonic anhydrase inhibitors. Mol Pharmacol 27: 493–498
Hansen P, Magid E (1966) Studies on a method of measuring carbonic anhydrase activity. Scand J Clin Lab Invest 18: 21–32
Hartman GD, Halczenko W, Smith RL, Sugrue MF, Mallorga P, Michelson SR, Randall WC, Schwam H, Sondey JM (1992) 4-Substituted thiophene-and furan-2-sulfonamides as topical carbonic anhydrase inhibitors. J Med Chem 35: 3822–3831
Henry RP, Cameron JA (1982) The distribution and partial characterization of carbonic anhydrase in selected aquatic and terrestrial Decapod crustaceans. J Exp Zool 221: 309–321
Ippolito JA, Christianson DW (1992) The contribution of halogen atoms to protein-ligand interactions. Int J Biol Macromol 14: 193–197
Itada N, Forster RE (1977) Carbonic anhydrase activity in intact red blood cells measured with 18O exchange. J Biol Chem 252: 3881–3890
Jain A, Huang SG, Whitesides GM (1994) Lack of effect of the length of oligoglycine-and oligo(ethylene glycol)-derived para-substituents on the affinity of benzenesulfonamides for carbonic anhydrase II in solution. J Am Chem Soc 116: 5057–5062
Jain A, Huang SG, Whitesides GM (1990) Rational drug design - the determination of active-site depth in solution by H-1-NMR spin-echo spectroscopy of carbonic anhydrase-sulfonamide complexes. Amer Chem Soc Abstr 200: 144-Orgn
Jain A, Whitesides GM, Alexander RS, Christianson DW (1994) Identification of two hydrophobic patches in the active-site cavity of human carbonic anhydrase II by solution-phase and solid-state studies and their use in the development of tight-binding inhibitors. J Med Chem 37: 2100–2105
Jarvet J, Olivson A, Mets U, Pooga M, Aguraiuja R, Lippmaa E (1989) C-13 and N-15 NMR and time-resolved fluorescence depolarization study of bovine carbonic anhydrase-4-methyl benzenesulfonamide complexes. Eur J Biochem 186: 287–290
Jayaweera GDS, MacNeil SA, Trager SF, Blackburn GM (1991) Synthesis of 2-substituted1,3,4-thiadiazole-5-sulfonamides as novel water-soluble inhibitors of carbonic anhydrase. Bioorg Med Chem Letters 1: 407–410
Jitianu A, Ilies MA, Scozzafava A, Supuran CT (1997) Complexes with biologically active ligands. 8. Synthesis and carbonic anhydrase inhibitory activity of 5-benzoylamido-and 5-(3-nitrobenzoylamido)-1,3,4-thiadiazole-2-sulfonamide and their metal complexes. Main Group Metal Chem 20: 151–156
Kanamori K, Roberts JD (1983) Nitrogen-15 nuclear magnetic resonance study of benzene sulfonamide and cyanate binding to carbonic anhydrase. Biochemistry 22: 2658–2664
Kannan KK, Vaara I, Notstrand B, Lövgren S, Borell A, Fridborg K, Petef M (1977) Structure and function of carbonic anhydrase: comparative studies of sulfonamide binding to human erythrocyte carbonic anhydrases B and C. In: GCK Roberts (ed): Proc Symp Drug Action Molecular Level, MacMillan, London, 73–91
Khalifah RG (1971) The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 246: 2561–2573
King RW, Burgen ASV (1976) Kinetic aspects of structure-activity relations: The binding of sulfonamides by carbonic anhydrase. Proc R Soc London 193: 107–125
Krebs JF, Fierke CA (1993) Determinants of catalytic activity and stability of carbonic anhydrase II as revealed by random mutagenesis. J Biol Chem 268: 948–954
Kumari P (1984) The synthesis of novel inhibitors for carbonic anhydrase. M.Sc. Thesis,Sheffield University
Leo A, Hansch CW, Elkins D (1971) Partition coefficients and their uses. Chem Rev 71:525
Lichter PR, Newman LP, Wheeler NC, Beall OV (1978) Tolerance to carbonic anhydrase inhibitors. Am J Ophthalmol 85: 495–502
Liebman KC, Alford D, Boudet RA (1961) Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther 131: 271–274
Lippa EA, Carlson L-E, Ehinger B, Eriksson L-O, Finnstrom K, Holmin C, Nilsson S-EG, Nyman K, Raitta C, Ringvold A et al (1992) Dose response and duration of action of dorzolamide, a topical carbonic anhydrase inhibitor. Arch Ophthalmol 110: 495–499
Lippa EA, von Denffer HA, Hofmann HM, Brunner-Ferber FL (1988) Local tolerance and activity of MK-927, a novel topical carbonic anhydrase inhibitor. Arch Opthalmol 106: 1694–1696
Luca C, Barboiu M, Supuran CT (1991) Carbonic-anhydrase inhibitors. 7. Stability-constants of complex inhibitors and their mechanism of action. Rev Roum Chim 36: 1169–1173
Mann T, Keilin D (1940) Sulfanilamide as a specific inhibitor of carbonic anhydrase. Nature 146: 164–165
Manole G, Maior O, Supuran CT (1993) Carbonic-anhydrase inhibitors. 17. Complexes of heterocyclic sulfonamides with Ru(II), Rh(III) and Au(III) are very strong dual inhibitors of isozymes-I and isozymes-II. Rev Roum Chim 38: 475–479
Maren TH (1960) A simplified micromethod for the determination of carbonic anhydrase and its inhibitors. J Pharmacol Exp Ther 130: 26–29
Maren TH (1967) Carbonic anhydrase: Chemistry, physiology, and inhibition. Physiol Rev 47: 595–781
Maren TH (1974) HCO –3 formation in aqueous humour. Mechanism and relation to the treatment of glaucoma. Invest Ophthalmol 13: 479–484
Maren TH (1976) Relations between structure and biological activity of sulfonamides. Ann Rev Pharm Toxicol 16: 309–327
Maren TH (1987) Carbonic anhydrase: General perspectives and advances in glaucoma research. Drug Dev Res 10: 255–276
Maren TH, Bar-Ilan A (1987) The effect of 6-OH benzo[b]thiophene-2-sulfonamide, a new topical carbonic anhydrase inhibitor, on intraocular pressure in rabbits. Invest Ophthalmol Visual Sci 28: 268
Maren TH, Bar-Ilan A, Conroy CW, Brechue WF (1990) Chemical and pharmacological properties of MK-927, a sulfonamide carbonic anhydrase inhibitor that lowers intraocular pressure by the topical route. Exp Eye Res 50: 27–36
Maren TH, Haywood JR, Chapman SK, Zimmerman TZ (1977) The pharmacology of methazolamide in relation to the treatment of glaucoma. Invest Ophthalmol Visual Sci 16: 730–742
Maren TH, Jankowska L, Sanyal G, Edelhauser HF (1983) The transcorneal permeability of sulfonamide carbonic anhydrase inhibitors and their effect on aqueous humour secretion. Exp Eye Res 36: 457–480
McIntosh JE (1968) Assay of carbonic anhydrase by titration at constant pH. Biochem J 109: 203–207
Meldrum NU, Roughton FJW (1933) Carbonic anhydrase: Its preparation and properties. J Physiol 80: 113–142
Miller WH, Dessert AM, Roblin RO Jr (1950) Heterocyclic sulfonamides as carbonic anhydrase inhibitors. J Am Chem Soc 72: 4893–4896
Nair SK, Krebs JF, Christianson DW, Fierke CA (1995) Structural basis of inhibitor affinity to variants of human carbonic anhydrase II. Biochemistry 34: 3981–3984
Okuyama T, Sato S, Zhu XL, Waheed A, Sly WS (1992) Human carbonic anhydrase-IV-cDNA cloning, sequence comparison, and expansion in COS cell membranes. Proc Nail Acad Sci USA 89: 1315–1319
Peters G, Roch-Ramel F (1969) Diuretics In: H Herken (ed): Handbook of Experimental Pharmacology, Springer, Heidelberg, 257
Philpot FJ, Philpot J (1936) A modified calorimetric estimation of carbonic anhydrase. Biochem J 30: 2191–2193
Pocker Y, Beug MW (1972) Kinetic studies of bovine carbonic anhydrase catalyzed hydrolyses ofp-substituted phenyl esters. Biochemistry 11: 698–707
Ponticello GS, Freedman MB, Habecker CN, Lyle PA, Schwam H, Varga SL, Christy ME, Randall WC, Baldwin JJ (1987) Thienothiopyran-2-sulfonamides: A novel class of water-soluble carbonic anhydrase inhibitors. J Med Chem 30: 591–597
Poulton DJ, Baldwin HW (1967) Oxygen exchange between carbonate and bicarbonate ions and water. I. Exchange in the absence of added catalysts. Can J Chem 45: 1045–1050
Prugh JD, Hartman GD, Mallorga PJ, McKeever BM, Michelson SR, Murcko MA, Schwam H, Smith RL, Sondey JM, Springer JP, Sugrue MF (1991) New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-Substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted thieno[3,2-b]thiophene-2-sulfonamides. J Med Chem 34: 1805–1818
Putnam ML, Schoenwald RD, Duffel MW, Barfknecht CF, Segarra TM, Campbell DA (1987) Ocular disposition of aminozolamide in the rabbit eye. Invest Ophthalmol Visual Sci 28: 1373–1382
Rossi KA, Merz Jr, KM, Smith GM, Baldwin JJ (1995) Application of the free energy perturbation method to human carbonic anhydrase II inhibitors. J Med Chem 38: 2061–2069
Trager SF, Blackburn GM (1990) U.S. Pat. 4,975,446, December 4th
Trager SF, Blackburn GM (1991) U.S. Pat 4,985,417, January 15th
Schoenwald RD, Eller MG, Dixson JA, Barfknecht CF (1984) Topical carbonic anhydrase inhibitors. J Med Chem 27: 810–812
Schwam H, Michelson SR, deSolms SJ, Deprat P, Gautheron P, Shepard KL, Smith RL, Sugrue MF (1988) Carbonic anhydrase inhibitors (CAIs): Correlation between reactivity with reduced glutathione (GSH) and induction of contact sensitivity in the guinea pig. Abstr., 8th Int. Cong. Eye Res. 116
Sigal GB, Whitesides GM (1996) Benzenesulfonamide-peptide conjugates as probes for secondary binding sites near the active site of carbonic anhydrase. Bioorg Med Chem Letters 6, 5: 559–564
Silverman DN (1982) Carbonic anhydrase: Oxygen-18 exchange catalyzed by an enzyme with rate-contributing proton-transfer steps. Methods Enzymol 87: 732–752
Silverman DN, Lindskog S (1988) The catalytic mechanism of carbonic anhydrase: Implications of a rate-limiting protolysis of water. Acc Chem Res 21: 30–36
Sugrue MF, Gautheron P, Grove J, Mallorga P, Schwam H, Viader P, Baldwin JJ, Ponticello GS (1988) MK-927: A topically effective ocular hypotensive carbonic anhydrase (CA) inhibitor in rabbits. Invest Ophthalmol Visual Sci 29: 81
Sugrue MF, Gautheron P, Mallorga P, Nolan TE, Graham SL, Scwam H, Shepard KL, Smith RL (1990) L-662,583 is a topically effective ocular hypotensive carbonic anhydrase inhibitor in experimental animals. Br J Pharmacol 99: 59–64
Sugrue MF, Gautheron P, Schmitt C, Viader MP, Conquet P, Smith RL, Share NN, Stone CA (1985) On the pharmacology of L-645–151: A topically effective ocular hypotensive carbonic anhydrase inhibitor. J Pharmacol Exp Ther 232: 534–540
Sugrue MF, Mallorga P, Schwam H, Baldwin JJ, Ponticello GS (1989) Invest Ophthalmol Visual Sci 30: 99
Sugrue MF, Mallorga P, Schwam H, Baldwin JJ, Ponticello GS (1990) A comparison of L671,152 and MK-927, two topically effective ocular hypotensive carbonic anhydrase inhibitors, in experimental animals. Current Eye Res 9: 607–615
Supuran CT (1993) Carbonic-anhydrase inhibitors. 16. Complex inhibitors containing metal-ions in high oxidation-states (V(IV)-Ce(IV)-Th(IV)-U(VI)). Rev Roum Chim 38: 229–236
Supuran CT (1996) Carbonic-anhydrase inhibitors. 25. Thienothiopyran sulfonamides - A novel class of complexing agents for the preparation of dual enzyme-inhibitors. Rev Roum Chim 41: 495–499
Supuran CT (1996) Carbonic-anhydrase inhibitors. 26. Preparation and inhibitory properties of coordination-compounds 1,3,4-thiadiazole-2,5-disulfonamide. Rev Roum Chim 41: 653–659
Supuran CT, Almajan GL (1995) Carbonic-anhydrase inhibitors. 34. Synthesis and biological-activity of coordination-compounds of 5-pivaloylamido-1,3,4-thiadiazole-2-sulfonamide with divalent metal-ions. Main Group Metal Chem 18: 347–351
Supuran CT, Andruh M (1994) Carbonic-anhydrase inhibitors. 18. Coordination-compounds of heterocyclic sulfonamides with main-group trivalent cations are potent isozyme-II inhibitors. Rev Roum Chim 39: 1229–1234
Supuran CT, Scozzafava A (1997) Novel aromatic/heterocyclic sulfonamides and their metal complexes as inhibitors of carbonic anhydrase isozyme I, II and IV. J Enz Inhib 12: 37–51
Supuran CT, Andruh M, Puscas I (1990) Carbonic-anhydrase inhibitors. 1. Metal-complexes of sulfonamides—A novel class of carbonic-anhydrase inhibitors. Rev Roum Chim 35: 393–399
Supuran CT, Manole G, Andruh M (1993) Carbonic-anhydrase inhibitors. 11. Coordination-compounds of heterocyclic sulfonamides with lanthanides are potent inhibitors of isozyme-I and isozyme-II. J Inorg Biochem 49: 97–103
Supuran CT, Manole G, Manzatu I (1992) Carbonic-anhydrase inhibitors. 12. Lanthanide complexes with acetazolamide as dual inhibitors. Rev Roum Chim 37: 739–744
Tashian RE (1989) The carbonic anhydrases: Widening perspectives on their evolution, expression and function. Bioessays 10: 186–192
Vedani A, Meyer Jr ER (1984) Structure-activity relationships of sulfonamide drugs and human carbonic anhydrase C: Modelling of inhibitor molecules into the receptor site of the enzyme with an interactive computer graphics display. J Pharm Sci 73: 352–358
Venta PJ, Montgomery JC, Tashian RE (1987) Molecular genetics of carbonic anhydrase isozymes. In: MC Rattazzi, JG Scandalios, GS Whitt (eds): Isozymes: Current Topics in Biological and Medical Research, Liss AR, New York, 59–72
Vidgren J, Liljas A, Walker NPC (1990) Refined structure of acetazolamide complex of human carbonic anhydrases II at 1.9 Å. Int Biol Macromol 12: 342–344
Wang R-F, Serle JB, Podos SM, Severin CH, Sugrue MF (1989) Invest Ophthalmol Visual Sci 30: 99
Werner EB, Gerber DS, Yodor YJ (1987) Effect of a typical carbonic anhydrase inhibitor, 6-hydroxybenzo[b]thiophene-2-sulfonamide on Intraocular pressure in normotensive subjects. Can J Ophthalmol 22: 316–319
Wilkerson M, Cyrlin M, Lippa EA, Esposito D, Deasy D, Panebianco D, Fazio R, Yablonski M, Shields MB (1993) Four week safety and efficacy study of dorzolamide, a novel, active topical carbonic anhydrase inhibitor. Arch Ophthalmol 111: 1343–1350
Woltersdorf Jr OW, Schwam H, Bicking JB, Brown SL, deSolms SJ, Fishman DR, Graham SL, Gautheron PD, Hoffman JM, Larson RD et al (1989) Topically active carbonic anhydrase inhibitors. 1. O-Acyl derivatives of 6-hydroxybenzothiazole-2-sulfonamide J Med Chem 32: 2486–2492
Zhang X-R (1995) Studies on water-soluble sulfonamide inhibitors of carbonic anhydrase. Ph.D. Thesis, Sheffield University
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Mansoor, U.F., Zhang, XR., Blackburn, G.M. (2000). The design of new carbonic anhydrase inhibitors. In: Chegwidden, W.R., Carter, N.D., Edwards, Y.H. (eds) The Carbonic Anhydrases. EXS 90, vol 90. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-8446-4_22
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