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Chemical Compound Review

Ethamide     6-ethoxybenzothiazole-2- sulfonamide

Synonyms: Cardrase, Mingoral, Redupresin, Etoxzolamide, Glaucotensil, ...
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Disease relevance of Ethamide


High impact information on Ethamide

  • We measured the concentration of CA by titration with a sulfonamide inhibitor, ethoxzolamide, obtaining an average value of 3.8 mumol/mg of microsomal membrane protein [4].
  • Injected CA accelerated the CO2/HCO3(-)-induced acidification severalfold, which was blocked by ethoxyzolamide and was independent of MCT1 expression [5].
  • Inhibition of NHE activity by amiloride inhibits regeneration of alkaline microdomains after cytoplasmic acidification, whereas the inhibition of CAII activity with ethoxyzolamide inhibits acidification of dendrites [6].
  • Glucokinase is contraindicated by the inverse relationship between hepatic glycogenesis and ATP availability in the ethoxyzolamide-treated preparations [7].
  • Treatment of algae with the CA inhibitors acetazolamide and ethoxyzolamide decreased photosynthetic oxygen evolution along the stalk but not at the rhizoid, indicating that CA facilitates inorganic carbon uptake in the apical portions of the alga [8].

Biological context of Ethamide

  • Even at the highest ethoxzolamide concentration used (10(-6) M), no effect was observed either on the amplitude of the compound nerve action potential or on the conduction velocity of group I fibres in the ischiadic nerve, suggesting that ethoxzolamide did not affect the mechanisms responsible for spike generation or conduction in the motor fibres [9].
  • This newly synthesized derivative of ethoxyzolamide has demonstrated clinical efficacy for use as an ophthalmic drug to lower intraocular pressure [10].
  • After preincubation of platelet rich plasma with 10(-6) M ethoxzolamide the velocity of platelet aggregation was reduced by about 40% [11].
  • In the extraocular muscles, ETZ did not alter twitch kinetics [12].
  • EZ reduced the light-saturated photosynthesis, the saturation radiance and the affinity of inorganic carbon for photosynthesis, raised inorganic carbon compensation point and enhanced the inhibition of photosynthesis by high O(2) and light [13].

Anatomical context of Ethamide


Associations of Ethamide with other chemical compounds


Gene context of Ethamide

  • Analysis of the kinetic properties of this carbonic anhydrase yielded a Km value of 1.0 mM, a catalytic-centre activity kcat. of 130000 s-1 and an inhibition constant Ki towards ethoxzolamide of 0.3 nM [23].
  • Indeed, both the very good hCA IV inhibitors (acetazolamide and ethoxzolamide) as well as the quite weak hCA IV inhibitors (methazolamide, dorzolamide, or dichlorophanamide) are effective in lowering IOP when administered either systemically or topically [24].
  • Maximal induced depolarization occurred at a psi mc of +50 mV whereas ethoxzolamide exerted minimal effect on psi mc when the ERP was approached either by voltage clamping the apical membrane or by the addition of amiloride [25].
  • Electrometric assays for CA activity revealed that whole cell extracts containing the recombinant protein significantly enhanced the rate of conversion of CO2 to HCO3- and that 98% of this catalytic activity was inhibited by ethoxyzolamide, a well-characterized CA inhibitor [26].
  • Similar to pdcd4, carbonic anhydrase inhibitor ethoxyzolamide reduces growth of several endocrine tumor cell lines [27].

Analytical, diagnostic and therapeutic context of Ethamide


  1. Pulmonary vasodilation by acetazolamide during hypoxia is unrelated to carbonic anhydrase inhibition. H??hne, C., Pickerodt, P.A., Francis, R.C., Boemke, W., Swenson, E.R. Am. J. Physiol. Lung Cell Mol. Physiol. (2007) [Pubmed]
  2. Treatment of duodenal ulcers with ethoxzolamide, an inhibitor of gastric mucosa carbonic anhydrase. Puscas, I., Buzas, G. International journal of clinical pharmacology, therapy, and toxicology. (1986) [Pubmed]
  3. Treatment of secondary recurrent and early latent syphilis with penicillin and ethamide: clinical and experimental evaluation. Mordovtsev, V.N., Bednova, V.N., Nazarova, A.J. Dermatologische Monatschrift. (1987) [Pubmed]
  4. Carbonic anhydrase in the membrane of the endoplasmic reticulum of male rat liver. Ono, Y., Ridderstråle, Y., Forster, R.E., Chu, Z.G., Dodgson, S.J. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  5. Transport activity of MCT1 expressed in Xenopus oocytes is increased by interaction with carbonic anhydrase. Becker, H.M., Hirnet, D., Fecher-Trost, C., Sültemeyer, D., Deitmer, J.W. J. Biol. Chem. (2005) [Pubmed]
  6. pH microdomains in oligodendrocytes. Ro, H.A., Carson, J.H. J. Biol. Chem. (2004) [Pubmed]
  7. Glycogenesis from glucose and ureagenesis in isolated perfused rat livers. Influence of ammonium ion, norvaline, and ethoxyzolamide. Bode, A.M., Foster, J.D., Nordlie, R.C. J. Biol. Chem. (1994) [Pubmed]
  8. Asymmetric subcellular mRNA distribution correlates with carbonic anhydrase activity in Acetabularia acetabulum. Serikawa, K.A., Porterfield, D.M., Mandoli, D.F. Plant Physiol. (2001) [Pubmed]
  9. Effects of inhibiting carbonic anhydrase on isometric contraction of frog skeletal muscle. Scheid, P., Siffert, W. J. Physiol. (Lond.) (1985) [Pubmed]
  10. Stability studies of topical carbonic anhydrase inhibitor 6-hydroxyethoxy-2-benzothiazole sulfonamide. Chiang, C.H., Hsieh, C.H., Lu, D.W., Kao, K.D. Journal of pharmaceutical sciences. (1992) [Pubmed]
  11. The effect of carbonic anhydrase inhibition on the velocity of thrombin-stimulated platelet aggregation under physiological conditions. Siffert, W., Fox, G., Gros, G. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  12. Carbonic anhydrase isoform expression and functional role in rodent extraocular muscle. Andrade, F.H., Hatala, D.A., McMullen, C.A. Pflugers Arch. (2004) [Pubmed]
  13. Roles of carbonic anhydrase in photosynthesis of Skeletonema costatum. Chen, X.W., Gao, K.S. Zhi Wu Sheng Li Yu Fen Zi Sheng Wu Xue Xue Bao (2004) [Pubmed]
  14. Carbonic anhydrase C in white-skeletal-muscle tissue. Siffert, W., Gros, G. Biochem. J. (1982) [Pubmed]
  15. The effect of carbonic anhydrase inhibitors on the anionic composition of sheep's parotid saliva. With an appendix on uncatalysed carbon dioxide-water kinetics by P. T. McTigue. Blair-West, J.R., Fernley, R.T., Nelson, J.F., Wintour, E.M., Wright, R.D. J. Physiol. (Lond.) (1980) [Pubmed]
  16. Intestinal bicarbonate secretion in Amphiuma measured by pH stat in vitro: relationship with metabolism and transport of sodium and chloride ions. Imon, M.A., White, J.F. J. Physiol. (Lond.) (1981) [Pubmed]
  17. A new chloroplast envelope carbonic anhydrase activity is induced during acclimation to low inorganic carbon concentrations in Chlamydomonas reinhardtii. Villarejo, A., Rolland, N., Martínez, F., Sültemeyer, D.F. Planta (2001) [Pubmed]
  18. Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol. Wang, B., Samanani, N., Roth, S.H., Archer, D.P. Anesthesiology (2003) [Pubmed]
  19. CO2-stimulated NaCl absorption in the mouse renal cortical thick ascending limb of Henle. Evidence for synchronous Na +/H+ and Cl-/HCO3- exchange in apical plasma membranes. Friedman, P.A., Andreoli, T.E. J. Gen. Physiol. (1982) [Pubmed]
  20. 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]
  21. Inhibition of muscle carbonic anhydrase slows the Ca(2+) transient in rat skeletal muscle fibers. Wetzel, P., Kleinke, T., Papadopoulos, S., Gros, G. Am. J. Physiol., Cell Physiol. (2002) [Pubmed]
  22. Light-induced stimulation of carbonic anhydrase activity in pea thylakoids. Moskvin, O.V., Ivanov, B.N., Ignatova, L.K., Kollmeier, M.A. FEBS Lett. (2000) [Pubmed]
  23. Carbonic anhydrase in human platelets. Siffert, W., Gros, G. Biochem. J. (1984) [Pubmed]
  24. Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Innocenti, A., Firnges, M.A., Antel, J., Wurl, M., Scozzafava, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  25. Electrogenic active proton pump in Rana esculenta skin and its role in sodium ion transport. Ehrenfeld, J., Garcia-Romeu, F., Harvey, B.J. J. Physiol. (Lond.) (1985) [Pubmed]
  26. Cloning, characterization and expression of carbonic anhydrase from the cyanobacterium Synechocystis PCC6803. So, A.K., Espie, G.S. Plant Mol. Biol. (1998) [Pubmed]
  27. Pdcd4 inhibits growth of tumor cells by suppression of carbonic anhydrase type II. Lankat-Buttgereit, B., Gregel, C., Knolle, A., Hasilik, A., Arnold, R., Göke, R. Mol. Cell. Endocrinol. (2004) [Pubmed]
  28. Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. Perez Velazquez, J.L. Eur. J. Neurosci. (2003) [Pubmed]
  29. Relations among IOP reduction, ocular disposition and pharmacology of the carbonic anhydrase inhibitor ethoxzolamide. Maren, T.H., Brechue, W.F., Bar-Ilan, A. Exp. Eye Res. (1992) [Pubmed]
  30. Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus. White, A.M., Platt, B. Experimental brain research. Experimentelle Hirnforschung. Expérimentation cérébrale. (2001) [Pubmed]
  31. Determination of ethoxzolamide in the iris/ciliary body of the rabbit eye by high-performance liquid chromatography: comparison of tissue levels following intravenous and topical administrations. Eller, M.G., Schoenwald, R.D. Journal of pharmaceutical sciences. (1984) [Pubmed]
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