The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents

Current Topics in Medicinal Chemistry

Volumn 7, Issue 9, 2007, Pages 849-854

  Mincione, Francesco ^a   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a Ospedale di Pescia   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 THIAZOLE 2 SULFONAMIDE DERIVATIVE; 2 HYDROXYPROPYL BETA CYCLODEXTRIN; ACETAZOLAMIDE; ANTIGLAUCOMA AGENT; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BRINZOLAMIDE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; DORZOLAMIDE; LATANOPROST; METHAZOLAMIDE; PROSTAGLANDIN; SULFONAMIDE; TIMOLOL; UNCLASSIFIED DRUG; UNOPROSTONE ISOPROPYL ESTER;

ANOREXIA; AQUEOUS HUMOR FLOW; BITTER TASTE; BLURRED VISION; BURNING SENSATION; COMBINATION CHEMOTHERAPY; CONTACT ALLERGY; DEMENTIA; DEPRESSION; DIABETIC RETINOPATHY; DISEASE ASSOCIATION; DRUG EFFICACY; DRUG MECHANISM; DRUG PENETRATION; DRUG POTENTIATION; DRUG SOLUBILITY; EYE DISEASE; FATIGUE; GASTROINTESTINAL IRRITATION; GLAUCOMA; HUMAN; INTRAOCULAR HYPERTENSION; INTRAOCULAR PRESSURE; LIBIDO DISORDER; MALAISE; METABOLIC ACIDOSIS; MONOTHERAPY; MYOPIA; NEPHROLITHIASIS; NONHUMAN; PARESTHESIA; PRURITUS; RETINA EDEMA; RETINA ISCHEMIA; RETINA MACULA DEGENERATION; RETINA MACULA EDEMA; RETINITIS PIGMENTOSA; REVIEW; SIDE EFFECT; SKIN TINGLING; TASTE DISORDER; VISUAL ACUITY; WEIGHT REDUCTION;

CARBONIC ANHYDRASE INHIBITORS; EYE DISEASES; GLAUCOMA; HUMANS; MOLECULAR STRUCTURE; SULFONAMIDES;

EID: 34249739237     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802607780636735     Document Type: Review

References (51)

1. Friedenwald, J.S. The formation of the intraocular fluid. Am. J. Ophthalmol. 1949, 32, 9-27.
2. Kinsey, V.E. Comparative chemistry of of aqueous humor in posterior and anterior chambers of rabbit eye. Arch. Ophthalmol. 1953, 50, 401-417.
3. Kinsey, V.E.; Barany, E. The rate flow of aqueous humor. II. Derivation of rate of flow and its physiologic significance. Am. J. Ophthalmol. 1949, 32, 189-202.
4. Wistrand, P.J. Carbonic anhydrase in the anterior uvea of the rabbit. Acta Physiol. Scand. 1951, 24, 144-148.
5. Becker, B. The mechanism of the fall in intraocular pressure by the carbonic anhydrase inhibitor Diamox. Am. J. Ophthalmol. 1955, 39, 177-183.
6. Kinsey, V.E.; Reddy, D.V.N. Turnover of total carbon dioxide in aqueous humors and the effect thereon of acetazolamide. Arch. Ophthalmol. 1959, 62, 78-83.
7. Sugrue, M.F. The pharmacology of antiglaucoma drugs. Pharmacol. Ther. 1989, 43, 91-138.
8. Bartlett, J.D.; Jaanus, S.D. Clinical ocular pharmacology, Butterworth, Boston, 1989; pp. 254-263.
9. Maren, T.H. Carbonic anhydrase: Chemistry, physiology and inhibition. Physiol. Rev. 1967, 47, 595-781.
10. Soltau, J.B.; Zimmerman, T.J. Changing paradigms in the medical treatment of glaucoma. Surv. Ophthalmol. 2002, 47, S2-S5.
11. Hoyng, P.F.J.; Kitazawa, Y. Medical treatment of normal tension glaucoma. Surv. Ophthalmol. 2002, 47, S116-S124.
12. Maren, T.H. The development of topical carbonic anhydrase inhibitors. J. Glaucoma 1995, 4, 49-62.
13. Supuran, C.T.; Scozzafava, A. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin. Ther. Pat. 2000, 10, 575-600.
14. Supuran, C.T.; Scozzafava, A. Carbonic anhydrase inhibitors. Curr. Med. Chem.- Immunol.; End. Metab. Agents, 2001, 1, 61-97.
15. Mincione, F.; Starnotti, M.; Masini, E.; Bacciottini, L.; Scrivanti, C.; Casini, A.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: Design of thioureido sulfonamides with potent isozyme II and XII inhibitory properties and intraocular pressure lowering activity in a rabbit model of glaucoma. Bioorg. Med. Chem. Lett. 2005, 15, 3821-7.
16. Supuran, C.T.; Scozzafava, A. Applications of carbonic anhydrase inhibitors and activators in therapy. Expert Opin. Ther. Pat. 2002, 12, 217-242.
17. Supuran, C.T.; Scozzafava, A.; Casini, A. Carbonic anhydrase inhibitors. Med. Res. Rev. 2003, 23, 146-189.
18. Sugrue, M.F. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Progr. Ret. Eye Res. 2000, 19, 87-112.
19. Innocenti, A.; Firnges, M.A.; Antel, J.; Wurl, M.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Bioorg. Med. Chem. Lett. 2005, 15, 1149-54.
20. Wistrand, P.J.; Lindqvist, A. Design of carbonic anhydrase inhibitors and the relationship between the pharmacodynamics and pharmacokinetics of acetazolamide. In Carbonic Anhydrase - From Biochemistry and Genetics to Physiology and Clinical Medicine. Botrè F.; Gros G.; Storey B.T. Eds.; VCH, Weinheim, 1991; pp. 352-378.
21. Maren, T.H.; Jankowska, L.; Sanyal, G.; Edelhauser, H.F. The transcorneal permeability of sulfonamide carbonic anhydrase innhibitors and their effect on aqueous humor secretion. Exp. Eye Res. 1983, 36, 457-480.
22. Kaur, I.P.; Smitha, R.; Aggarwal, D.; Kapil, M. Acetazolamide: Future perspectives in topical glaucoma therapeutics. Intern. J. Pharm. 2002, 248, 1-14.
23. Maus, T.L.; Larsson, L.I.; McLaren, J.W.; Brubaker, R.F. Comparison of dorzolamide and acetazolamide as suppresors of aqueous humor flow in humans. Arch. Ophthalmol. 1997, 115, 45-49.
24. Silver, L.H. Dose-response evaluation of the ocular hypotensive effect of brinzolamide ophthalmic suspension (Azopt). Brinzolamide dose-response study group. Surv. Ophthalmol. 2000, 44 (Suppl. 2), 147-153.
25. Supuran, C.T.; Scozzafava, A.; Casini, A. Development of sulfonamide carbonic anhydrase inhibitors (CAIs). In Carbonic anhydrase - Its Inhibitors and Activators, C.T. Supuran, A. Scozzafava, J. Conway Eds.; CRC Press, Boca Raton (FL), 2004; pp. 67-147.
26. Aalto-Korte, K. Contact allergy to dorzolamide eyedrops. Contact Dermatitis 1998, 39, 206.
27. Carlsen, J.; Durcan, J.; Swartz, M.; Crandall A. Nephrolithiasis with dorzolamide. Arch. Ophthalmol. 1999, 117, 1087-1088.
28. Thoe Schwartzenberg, G.W.; Trope, G.E. Anorexia, depression and dementia induced by dorzolamide eyedrops (Trusopt). Can. J. Ophthalmol. 1999, 34, 93-94.
29. Konowal, A.; Morrison, J.C.; Brown, S.V.; Cooke, D.L.; Maguire, L.J.; Verdier, D.V. Irreversible corneal decompensation in patients treated with topical dorzolamide. Am. J. Ophthalmol. 1999, 127, 403-406.
30. Borras J, Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincione G, Supuran CT Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/ heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: Is the tail more important than the ring ? Bioorg. Med. Chem. 1999, 7, 2397-2406.
31. Casini, A.; Scozzafava, A.; Mincione, F.; Menabuoni, L.; Ilies, M.A.; Supuran, C.T. Carbonic anhydrase inhibitors: Water soluble 4-sulfamoylphenylthioureas as topical intraocular pressure lowering agents with long lasting effects. J. Med. Chem. 2000, 43, 4884-4892.
32. Menabuoni, L.; Scozzafava, A.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C.T. Carbonic anhydrase inhibitors. Water-soluble, topically effective intraocular pressure lowering agents derived from isonicotinic acid and aromatic/heterocyclic sulfonamides: Is the tail more important than the ring ? J. Enz. Inhib. 1999, 14, 457-474
33. Mincione, G.; Menabuoni, L.; Briganti, F.; Scozzafava, A.; Mincione, F.; Supuran, C.T. Carbonic anhydrase inhibitors. Part 79. Synthesis and ocular pharmacology of topically acting sulfonamides incorporating GABA moieties in their molecule, with long-lasting intraocular pressure lowering properties. Eur. J. Pharm. Sci. 1999, 9, 185-199.
34. Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C.T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: Is the tail more important than the ring ? J. Med. Chem. 1999, 42, 2641-2650.
35. Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C.T. sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 1999, 42, 3690-3700.
36. Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C.T. Carbonic anhydrase inhibitors: Perfluoroalkyl/ aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure lowering agents with prolonged duration of action. J. Med. Chem. 2000, 43, 4542-4551.
37. Scozzafava, A.; Menabuoni, L.; Mincione, F.; Supuran, C.T. Carbonic anhydrase inhibitors. A general approach for the preparation of water soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long lasting, topical intraocular pressure lowering properties. J. Med. Chem. 2002, 45, 1466-1476.
38. Supuran, C.T.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G. Carbonic anhydrase inhibitors. Part 70. Synthesis and ocular pharmacology of a new class of water-soluble, topically effective intraocular pressure lowering agents derived from nicotinic acid and aromatic/heterocyclic sulfonamides. Eur. J. Med. Chem. 1999, 34, 799-808.
39. Wayman, L.; Larsson, L.I.; Maus, T.; Alm, A.; Brubaker, R. Comparison of dorzolamide and timolol as suppressors of aqueous humor flow in humans. Arch. Ophthalmol. 1997, 115, 1368-1371.
40. Alm, A. Prostaglandin derivates as ocular hypotensive agents. Progress Ret. Eye Res. 1998, 17, 291-312.
41. Larsson, L.I.; Alm, A. Aqueous humor flow in human eyes treated with dorzolamide and different doses of acetazolamide. Arch. Ophthalmol. 1998, 116, 19-24.
42. Vanlandingham, B.D.; Brubaker, R.F. Combined effect of dorzolamide and latanoprost on the rate of aqueous humor flow. Am. J. Ophthalmol. 1998, 126, 191-196.
43. Higginbotham, E.J.; Diestelhorst, M.; Pfeiffer, N.; Rouland, J.F.; Alm, A. The efficacy and safety of unfixed and fixed combinations of latanoprost and other antiglaucoma medications. Surv. Ophthalmol. 2002, 47, S133-S140.
44. Maestrelli, F.; Mura, P.; Casini, A.; Mincione, F.; Scozzafava, A.; Supuran, C.T. Cyclodextrin complexes of sulfonamide carbonic anhydrase inhibitors as long lasting topically acting antiglaucoma agents. J. Pharm. Sci. 2002, 91, 2211-2219.
45. Piltz-Seymour, J.R.; Grunwald, J.E.; Hariprasad, S.M.; DuPont, J. Optic nerve blood flow is diminished in eyes of primary open-angle glaucoma suspects. Am. J. Ophthalmol. 2001, 132, 63-69.
46. Cox, S.N.; Hay, E.; Bird, A.C. Treatment of chronic macular edema with acetazolamide. Arch. Ophthalmol. 1988, 106, 1190-1195.
47. Grover, S.; Fishman, G.A.; Fiscella, R.G.; Adelman, A.E. Efficacy of dorzolamide hydrochloride in the management of chronic cystoid macular edema in patients with retinitis pigmentosa. Retina 1997, 17, 222-231.
48. Sponsel, W.E.; Harrison, J.; Elliott, W.R.; Trigo, Y.; Kavanagh, J.; Harris, A. Dorzolamide hydrochloride and visual function in normal eyes. Am. J. Ophthalmol. 1997, 123, 759-766.
49. Barnes, G.E.; Li, B.; Dean, T.; Chandler, M.L. Increased optic nerve head blood flow after 1 week of twice daily brinzolamide treatment in Dutchbelted rabbits. Survey Ophthalmol. 2000, 44(Suppl. 2), 131-140.
50. Orzalesi, N.; Pierrottet, C.; Porta, A.; Aschero, M. Long-term treatment of retinitis pigmentosa with acetazolamide. A pilot study. Graefes Arch. Clin. Exp. Ophthalmol. 1993, 231, 254-256.
51. Gonzalez, C. Serous retinal detachment. Value of acetazolamide. J. Fr. Ophthalmol. 1992, 15, 529-536.