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Chemical Compound Review

methazolamide     (NZ)-N-(3-methyl-5-sulfamoyl- 1,3,4...

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Disease relevance of methazolamide


Psychiatry related information on methazolamide


High impact information on methazolamide


Chemical compound and disease context of methazolamide


Biological context of methazolamide


Anatomical context of methazolamide

  • Methazolamide yielded a more profound lowering in the CO2 content of the aqueous humor, a reflection of the significant decrease in plasma CO2 content [16].
  • Due to their salt-like character, the new type of inhibitors reported here, unlike the classical, clinically used compounds (such as acetazolamide, methazolamide, and ethoxzolamide), are unable to penetrate through biological membranes, as shown by ex vivo and in vivo perfusion experiments in rats [17].
  • Methazolamide was administered topically to eyes of 4-7-day-old chick embryos in shell-free culture [14].
  • 6. The changes in slope and intercept induced by methazolamide are discussed in relation to effects on neurones containing carbonic anhydrase, which may include central chemoreceptors [18].
  • 2. In the same animals the effect on the ventilatory response to CO2 of subsequent inhibition of central nervous system (CNS) carbonic anhydrase was studied by infusing methazolamide (20 mg kg-1), an inhibitor which rapidly penetrates into brain tissue [18].

Associations of methazolamide with other chemical compounds


Gene context of methazolamide

  • An interesting behavior was evidenced for some of the ortho-substituted arylsulfonylcarbamato-sulfonamides, which showed higher affinities for the isozyme hCA I, as compared to hCA II and bCA IV (generally hCA I is 10-1000 less sensitive to "normal" sulfonamide inhibitors, such as acetazolamide, methazolamide or dorzolamide, as compared to hCA II) [24].
  • Inhibition of CA (methazolamide, 25 mg/kg) led in all groups to equivalent increments of urine pH, urine flow, and HCO3-, Na+, and K+ excretion [25].
  • Some of these derivatives showed good inhibitory potency against two human CA isozymes involved in important physiological processes, CA I, and CA II, of the same order of magnitude as the clinically used drugs acetazolamide and methazolamide [26].
  • The inhibition of the newly discovered cytosolic carbonic anhydrase isozyme XIII (CA XIII) has been investigated with a series of aromatic and heterocyclic sulfonamides, including some of the clinically used derivatives, such as acetazolamide, methazolamide, dichlorophenamide, dorzolamide, and valdecoxib [27].
  • Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors [28].

Analytical, diagnostic and therapeutic context of methazolamide


  1. Aplastic anemia and agranulocytosis in patients using methazolamide for glaucoma. Werblin, T.P., Pollack, I.P., Liss, R.A. JAMA (1979) [Pubmed]
  2. Methazolamide in acute mountain sickness. Forster, P. Lancet (1982) [Pubmed]
  3. Double-blind controlled study of methazolamide in the treatment of essential tremor. Busenbark, K., Pahwa, R., Hubble, J., Hopfensperger, K., Koller, W., Pogrebra, K. Neurology (1993) [Pubmed]
  4. Neutropenia with clozapine and methazolamide. Burke, W.J., Ranno, A.E. Journal of clinical psychopharmacology. (1994) [Pubmed]
  5. Methazolamide 1% in cyclodextrin solution lowers IOP in human ocular hypertension. Gudmundsdóttir, E., Stefánsson, E., Bjarnadóttir, G., Sigurjónsdóttir, J.F., Gudmundsdóttir, G., Masson, M., Loftsson, T. Invest. Ophthalmol. Vis. Sci. (2000) [Pubmed]
  6. Inhibition of the action of anticonvulsants by lithium treatment. Kadzielawa, K. Pharmacol. Biochem. Behav. (1979) [Pubmed]
  7. NaCl absorption in the rabbit ileum. Effect of acid-base variables. Charney, A.N., Egnor, R.W. Gastroenterology (1991) [Pubmed]
  8. Drug-protein interactions. Refined structures of three sulfonamide drug complexes of human carbonic anhydrase I enzyme. Chakravarty, S., Kannan, K.K. J. Mol. Biol. (1994) [Pubmed]
  9. Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. Nishimori, I., Minakuchi, T., Onishi, S., Vullo, D., Scozzafava, A., Supuran, C.T. J. Med. Chem. (2007) [Pubmed]
  10. The carbonic anhydrase inhibitors methazolamide and acetazolamide have different effects on the hypoxic ventilatory response in the anaesthetized cat. Teppema, L.J., Bijl, H., Mousavi Gourabi, B., Dahan, A. J. Physiol. (Lond.) (2006) [Pubmed]
  11. Focal CO2/H+ alters phrenic motor output response to chemical stimulation of cat pre-Botzinger complex in vivo. Solomon, I.C. J. Appl. Physiol. (2003) [Pubmed]
  12. Rebound of macular edema with continued use of methazolamide in patients with retinitis pigmentosa. Fishman, G.A., Glenn, A.M., Gilbert, L.D. Arch. Ophthalmol. (1993) [Pubmed]
  13. The anionic basis of fluid secretion by the rabbit mandibular salivary gland. Case, R.M., Hunter, M., Novak, I., Young, J.A. J. Physiol. (Lond.) (1984) [Pubmed]
  14. A role for carbonic anhydrase in early eye morphogenesis. Linser, P.J., Plunkett, J.A. Invest. Ophthalmol. Vis. Sci. (1989) [Pubmed]
  15. Effect of methazolamide on chronic macular edema in patients with retinitis pigmentosa. Fishman, G.A., Gilbert, L.D., Anderson, R.J., Marmor, M.F., Weleber, R.G., Viana, M.A. Ophthalmology (1994) [Pubmed]
  16. The effects of carbonic anhydrase inhibitors on aqueous humor chemistry and dynamics. Bar-Ilan, A., Pessah, N.I., Maren, T.H. Invest. Ophthalmol. Vis. Sci. (1984) [Pubmed]
  17. Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. Scozzafava, A., Briganti, F., Ilies, M.A., Supuran, C.T. J. Med. Chem. (2000) [Pubmed]
  18. Carbonic anhydrase and control of breathing: different effects of benzolamide and methazolamide in the anaesthetized cat. Teppema, L., Berkenbosch, A., DeGoede, J., Olievier, C. J. Physiol. (Lond.) (1995) [Pubmed]
  19. Epithelial carbonic anhydrases facilitate PCO2 and pH regulation in rat duodenal mucosa. Mizumori, M., Meyerowitz, J., Takeuchi, T., Lim, S., Lee, P., Supuran, C.T., Guth, P.H., Engel, E., Kaunitz, J.D., Akiba, Y. J. Physiol. (Lond.) (2006) [Pubmed]
  20. Investigations on the interaction of thyrotropin-releasing hormone (TRH) and MK-771 with central noradrenergic mechanisms. Lotti, V.J., Yarbrough, G.G., Clineschmidt, B.V. Psychopharmacology (Berl.) (1980) [Pubmed]
  21. Calcium metabolism in acidotic patients induced by carbonic anhydrase inhibitors: responses to citrate. Higashihara, E., Nutahara, K., Takeuchi, T., Shoji, N., Araie, M., Aso, Y. J. Urol. (1991) [Pubmed]
  22. Low-dose PGE2 mimics the duodenal secretory response to luminal acid in mice. Hirokawa, M., Furukawa, O., Guth, P.H., Engel, E., Kaunitz, J.D. Am. J. Physiol. Gastrointest. Liver Physiol. (2004) [Pubmed]
  23. The nonenzymatic displacement of the sulfamoyl group from different classes of aromatic compounds by glutathione and cysteine. Conroy, C.W., Schwam, H., Maren, T.H. Drug Metab. Dispos. (1984) [Pubmed]
  24. Carbonic anhydrase inhibitors: synthesis of Schiff bases of hydroxybenzaldehydes with aromatic sulfonamides and their reactions with arylsulfonyl isocyanates. Scozzafava, A., Banciu, M.D., Popescu, A., Supuran, C.T. J. Enzym. Inhib. (2000) [Pubmed]
  25. Localization and activity of renal carbonic anhydrase (CA) in CA-II deficient mice. Brechue, W.F., Kinne-Saffran, E., Kinne, R.K., Maren, T.H. Biochim. Biophys. Acta (1991) [Pubmed]
  26. Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. Ilies, M.A., Masereel, B., Rolin, S., Scozzafava, A., Câmpeanu, G., Cîmpeanu, V., Supuran, C.T. Bioorg. Med. Chem. (2004) [Pubmed]
  27. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design. Lehtonen, J.M., Parkkila, S., Vullo, D., Casini, A., Scozzafava, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  28. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors. Abbate, F., Casini, A., Scozzafava, A., Supuran, C.T. Journal of enzyme inhibition and medicinal chemistry. (2003) [Pubmed]
  29. Time course and disposition of methazolamide in human plasma and red blood cells. Bayne, W.F., Tao, F.T., Rogers, G., Chu, L.C., Theeuwes, F. Journal of pharmaceutical sciences. (1981) [Pubmed]
  30. Topical acetazolamide and methazolamide delivered by contact lenses. Friedman, Z., Allen, R.C., Raph, S.M. Arch. Ophthalmol. (1985) [Pubmed]
  31. Determination of methazolamide concentrations in human biological fluids using high performance liquid chromatography. Iyer, G.R., Taft, D.R. Journal of pharmaceutical and biomedical analysis. (1998) [Pubmed]
  32. The effect of topically administered carbonic anhydrase inhibitors on aqueous humor dynamics in rabbits. Stein, A., Pinke, R., Krupin, T., Glabb, E., Podos, S.M., Serle, J., Maren, T.H. Am. J. Ophthalmol. (1983) [Pubmed]
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