benzolamide

Summary

Summary: Selective renal carbonic anhydrase inhibitor. It may also be of use in certain cases of respiratory failure.

Top Publications

  1. Wetzel P, Hasse A, Papadopoulos S, Voipio J, Kaila K, Gros G. Extracellular carbonic anhydrase activity facilitates lactic acid transport in rat skeletal muscle fibres. J Physiol. 2001;531:743-56 pubmed
    ..2. Muscle fibres were exposed to 20 mM sodium lactate in the absence and presence of the CA inhibitors benzolamide (BZ), acetazolamide (AZ), chlorzolamide (CZ) and ethoxzolamide (EZ)...
  2. Makani S, Chesler M. Endogenous alkaline transients boost postsynaptic NMDA receptor responses in hippocampal CA1 pyramidal neurons. J Neurosci. 2007;27:7438-46 pubmed
    ..blocker methoxyverapamil hydrochloride but was absent in the presence of the carbonic anhydrase inhibitor benzolamide or when the exogenous enzyme was heat inactivated...
  3. Höhne C, Pickerodt P, Francis R, Boemke W, Swenson E. Pulmonary vasodilation by acetazolamide during hypoxia is unrelated to carbonic anhydrase inhibition. Am J Physiol Lung Cell Mol Physiol. 2007;292:L178-84 pubmed
    ..kg(-1).h(-1)), 3) oral acetazolamide (5 mg/kg), 4) benzolamide, a membrane-impermeant inhibitor, and 5) ethoxzolamide, a membrane-permeant inhibitor...
  4. Eminoğlu A, Vullo D, Aşık A, Çolak D, Çanakçı S, Beldüz A, et al. Sulfonamide inhibition studies of the β-carbonic anhydrase from the newly discovered bacterium Enterobacter sp. B13. Bioorg Med Chem Lett. 2016;26:1821-6 pubmed publisher
    ..7-96.5nM). Clinically used agents such as methazolamide, ethoxzolamide, dorzolamide, brinzolamide, benzolamide, zonisamide, sulthiame, sulpiride, topiramate and valdecoxib were slightly less effective inhibitors (KIs in ..
  5. Miracle C, Rieg T, Blantz R, Vallon V, Thomson S. Combined effects of carbonic anhydrase inhibitor and adenosine A1 receptor antagonist on hemodynamic and tubular function in the kidney. Kidney Blood Press Res. 2007;30:388-99 pubmed
    ..3 mg/kg i.v.) would prevent CAI (benzolamide 5 mg/kg i.v...
  6. Del Prete S, Vullo D, Di Fonzo P, Osman S, Alothman Z, Donald W, et al. Sulfonamide inhibition profile of the ?-carbonic anhydrase identified in the genome of the pathogenic bacterium Burkholderia pseudomallei the etiological agent responsible of melioidosis. Bioorg Med Chem Lett. 2017;27:490-495 pubmed publisher
    ..The inhibition constant value for this enzyme for 39 sulfonamide inhibitors was obtained. Acetazolamide, benzolamide and metanilamide were the most effective (KIs of 149-653nM) inhibitors of BpsCA? activity, whereas ..
  7. Sun X, Li J, Cui M, Bonanno J. Role of carbonic anhydrase IV in corneal endothelial HCO3- transport. Invest Ophthalmol Vis Sci. 2008;49:1048-55 pubmed publisher
    ..Apical CAIV was inhibited by benzolamide or siRNA knockdown of CAIV...
  8. Tong C, Chesler M. Modulation of spreading depression by changes in extracellular pH. J Neurophysiol. 2000;84:2449-57 pubmed
    ..In addition, a carbonic anhydrase inhibitor (benzolamide) was used to decrease buffering of the alkaline shift to investigate its role in the modulation of SD...
  9. Deng A, Wead L, Blantz R. Temporal adaptation of tubuloglomerular feedback: effects of COX-2. Kidney Int. 2004;66:2348-53 pubmed
    ..Kidney blood flow (RBF) and glomerular filtration rate (GFR) were measured before and during benzolamide (BNZ) infusion in control Wistar rats and rats concurrently receiving COX-2 inhibitors...
  10. Svichar N, Waheed A, Sly W, Hennings J, Hübner C, Chesler M. Carbonic anhydrases CA4 and CA14 both enhance AE3-mediated Cl--HCO3- exchange in hippocampal neurons. J Neurosci. 2009;29:3252-8 pubmed publisher
    ..alkalinization was enhanced when the extracellular CAs were inhibited by the poorly permeant CA blocker, benzolamide, or by inhibitory antibodies specific for either CA4 or CA14...

Detail Information

Publications62

  1. Wetzel P, Hasse A, Papadopoulos S, Voipio J, Kaila K, Gros G. Extracellular carbonic anhydrase activity facilitates lactic acid transport in rat skeletal muscle fibres. J Physiol. 2001;531:743-56 pubmed
    ..2. Muscle fibres were exposed to 20 mM sodium lactate in the absence and presence of the CA inhibitors benzolamide (BZ), acetazolamide (AZ), chlorzolamide (CZ) and ethoxzolamide (EZ)...
  2. Makani S, Chesler M. Endogenous alkaline transients boost postsynaptic NMDA receptor responses in hippocampal CA1 pyramidal neurons. J Neurosci. 2007;27:7438-46 pubmed
    ..blocker methoxyverapamil hydrochloride but was absent in the presence of the carbonic anhydrase inhibitor benzolamide or when the exogenous enzyme was heat inactivated...
  3. Höhne C, Pickerodt P, Francis R, Boemke W, Swenson E. Pulmonary vasodilation by acetazolamide during hypoxia is unrelated to carbonic anhydrase inhibition. Am J Physiol Lung Cell Mol Physiol. 2007;292:L178-84 pubmed
    ..kg(-1).h(-1)), 3) oral acetazolamide (5 mg/kg), 4) benzolamide, a membrane-impermeant inhibitor, and 5) ethoxzolamide, a membrane-permeant inhibitor...
  4. Eminoğlu A, Vullo D, Aşık A, Çolak D, Çanakçı S, Beldüz A, et al. Sulfonamide inhibition studies of the β-carbonic anhydrase from the newly discovered bacterium Enterobacter sp. B13. Bioorg Med Chem Lett. 2016;26:1821-6 pubmed publisher
    ..7-96.5nM). Clinically used agents such as methazolamide, ethoxzolamide, dorzolamide, brinzolamide, benzolamide, zonisamide, sulthiame, sulpiride, topiramate and valdecoxib were slightly less effective inhibitors (KIs in ..
  5. Miracle C, Rieg T, Blantz R, Vallon V, Thomson S. Combined effects of carbonic anhydrase inhibitor and adenosine A1 receptor antagonist on hemodynamic and tubular function in the kidney. Kidney Blood Press Res. 2007;30:388-99 pubmed
    ..3 mg/kg i.v.) would prevent CAI (benzolamide 5 mg/kg i.v...
  6. Del Prete S, Vullo D, Di Fonzo P, Osman S, Alothman Z, Donald W, et al. Sulfonamide inhibition profile of the ?-carbonic anhydrase identified in the genome of the pathogenic bacterium Burkholderia pseudomallei the etiological agent responsible of melioidosis. Bioorg Med Chem Lett. 2017;27:490-495 pubmed publisher
    ..The inhibition constant value for this enzyme for 39 sulfonamide inhibitors was obtained. Acetazolamide, benzolamide and metanilamide were the most effective (KIs of 149-653nM) inhibitors of BpsCA? activity, whereas ..
  7. Sun X, Li J, Cui M, Bonanno J. Role of carbonic anhydrase IV in corneal endothelial HCO3- transport. Invest Ophthalmol Vis Sci. 2008;49:1048-55 pubmed publisher
    ..Apical CAIV was inhibited by benzolamide or siRNA knockdown of CAIV...
  8. Tong C, Chesler M. Modulation of spreading depression by changes in extracellular pH. J Neurophysiol. 2000;84:2449-57 pubmed
    ..In addition, a carbonic anhydrase inhibitor (benzolamide) was used to decrease buffering of the alkaline shift to investigate its role in the modulation of SD...
  9. Deng A, Wead L, Blantz R. Temporal adaptation of tubuloglomerular feedback: effects of COX-2. Kidney Int. 2004;66:2348-53 pubmed
    ..Kidney blood flow (RBF) and glomerular filtration rate (GFR) were measured before and during benzolamide (BNZ) infusion in control Wistar rats and rats concurrently receiving COX-2 inhibitors...
  10. Svichar N, Waheed A, Sly W, Hennings J, Hübner C, Chesler M. Carbonic anhydrases CA4 and CA14 both enhance AE3-mediated Cl--HCO3- exchange in hippocampal neurons. J Neurosci. 2009;29:3252-8 pubmed publisher
    ..alkalinization was enhanced when the extracellular CAs were inhibited by the poorly permeant CA blocker, benzolamide, or by inhibitory antibodies specific for either CA4 or CA14...
  11. Teppema L, Berkenbosch A, Degoede J, Olievier C. Carbonic anhydrase and control of breathing: different effects of benzolamide and methazolamide in the anaesthetized cat. J Physiol. 1995;488 ( Pt 3):767-77 pubmed
    ..of inhibition of erythrocyte carbonic anhydrase on the ventilatory response to CO2 was studied by administering benzolamide (70 mg kg-1, i.v...
  12. Lamsa K, Kaila K. Ionic mechanisms of spontaneous GABAergic events in rat hippocampal slices exposed to 4-aminopyridine. J Neurophysiol. 1997;78:2582-91 pubmed
    ..Exposure to inhibitors of carbonic anhydrase, benzolamide (BA; 10 micro M) or ethoxyzolamide (EZA; 50 mu M) fully blocked the alkaline pHo transients and turned them ..
  13. Cincinelli A, Martellini T, Vullo D, Supuran C. Anion and sulfonamide inhibition studies of an α-carbonic anhydrase from the Antarctic hemoglobinless fish Chionodraco hamatus. Bioorg Med Chem Lett. 2015;25:5485-9 pubmed publisher
    ..Many clinically used drugs, such as acetazolamide, methazolamide, dorzolamide, brinzolamide, topiramate and benzolamide were low nanomolar inhibitors, with KIs in the range of 39.1-77.6 nM...
  14. Chandrashekar J, Yarmolinsky D, von Buchholtz L, Oka Y, Sly W, Ryba N, et al. The taste of carbonation. Science. 2009;326:443-5 pubmed publisher
    ..Together, these studies reveal the basis of the taste of carbonation as well as the contribution of taste cells in the orosensory response to CO2. ..
  15. Paalasmaa P, Kaila K. Role of voltage-gated calcium channels in the generation of activity-induced extracellular pH transients in the rat hippocampal slice. J Neurophysiol. 1996;75:2354-60 pubmed
    ..The present results indicate that much (in s. pyramidale perhaps all) of the pH-changing influx of Ca2+ is mediated by voltage-gated Ca2+ channels. ..
  16. Svichar N, Esquenazi S, Waheed A, Sly W, Chesler M. Functional demonstration of surface carbonic anhydrase IV activity on rat astrocytes. Glia. 2006;53:241-7 pubmed
    ..Prior work showed that the intracellular lactate-induced acidification (LIA) of astrocytes is diminished by benzolamide, a poorly permeant, nonspecific CA inhibitor...
  17. Deng A, Hammes J, Thomson S. Hemodynamics of early tubuloglomerular feedback resetting during reduced proximal reabsorption. Kidney Int. 2002;62:2136-43 pubmed
    Carbonic anhydrase inhibition with benzolamide reduces proximal reabsorption and activates tubuloglomerular feedback (TGF)...
  18. Hempleman S, Rodriguez T, Bhagat Y, Begay R. Benzolamide, acetazolamide, and signal transduction in avian intrapulmonary chemoreceptors. Am J Physiol Regul Integr Comp Physiol. 2000;279:R1988-95 pubmed
    ..CA inhibitor that is membrane permeable (iv acetazolamide) with one that is relatively membrane impermeable (iv benzolamide)...
  19. Vullo D, Del Prete S, Di Fonzo P, Carginale V, Donald W, Supuran C, et al. Comparison of the Sulfonamide Inhibition Profiles of the ?- and ?-Carbonic Anhydrases from the Pathogenic Bacterium Burkholderia pseudomallei. Molecules. 2017;22: pubmed publisher
    ..The best inhibition was observed with benzene-1,3-disulfonamides-benzolamide and its analogs acetazolamide and methazolamide-which showed KI in the range of 185-745 nM...
  20. Schneider H, Alt M, Klier M, Spiess A, Andes F, Waheed A, et al. GPI-anchored carbonic anhydrase IV displays both intra- and extracellular activity in cRNA-injected oocytes and in mouse neurons. Proc Natl Acad Sci U S A. 2013;110:1494-9 pubmed publisher
    ..Extra- and intracellular catalytic activity of CA IV could be pharmacologically dissected using benzolamide, the CA inhibitor, which is relatively slowly membrane-permeable...
  21. Tong C, Brion L, Suarez C, Chesler M. Interstitial carbonic anhydrase (CA) activity in brain is attributable to membrane-bound CA type IV. J Neurosci. 2000;20:8247-53 pubmed
    ..The effect of benzolamide (a poorly permeant CA inhibitor) on evoked pH(o) shifts was diminished greatly in the PI-PLC-treated tissue, ..
  22. Gottfried J, Chesler M. Endogenous H+ modulation of NMDA receptor-mediated EPSCs revealed by carbonic anhydrase inhibition in rat hippocampus. J Physiol. 1994;478 Pt 3:373-8 pubmed
    ..Here we amplify these pH shifts using benzolamide (a carbonic anhydrase inhibitor) and describe concomitant effects on EPSCs in whole-cell clamped CA1 neurones ..
  23. Shimoda L, Luke T, Sylvester J, Shih H, Jain A, Swenson E. Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition. Am J Physiol Lung Cell Mol Physiol. 2007;292:L1002-12 pubmed
    ..Using fluorescent microscopy, we tested the effect of AZ as well as two other potent CA inhibitors, benzolamide and ethoxzolamide, which exhibit low and high membrane permeability, respectively, on hypoxia-induced responses ..
  24. Vargas L, Pinilla O, Díaz R, Sepúlveda D, Swenson E, Perez N, et al. Carbonic anhydrase inhibitors reduce cardiac dysfunction after sustained coronary artery ligation in rats. Cardiovasc Pathol. 2016;25:468-477 pubmed publisher
    Two potent carbonic anhydrase (CA) inhibitors with widely differing membrane permeability, poorly diffusible benzolamide (BZ), and highly diffusible ethoxzolamide (ETZ) were assessed to determine whether they can reduce cardiac ..
  25. Wolfensberger T, Chiang R, Takeuchi A, Marmor M. Inhibition of membrane-bound carbonic anhydrase enhances subretinal fluid absorption and retinal adhesiveness. Graefes Arch Clin Exp Ophthalmol. 2000;238:76-80 pubmed
    ..This study investigates how benzolamide, a carbonic anhydrase inhibitor which does not readily penetrate cell membranes, modulates retinal pigment ..
  26. Goldfarb D, Sly W, Waheed A, Charney A. Acid-base effects on electrolyte transport in CA II-deficient mouse colon. Am J Physiol Gastrointest Liver Physiol. 2000;278:G409-15 pubmed
    ..Membrane-permeant methazolamide, but not impermeant benzolamide, at 0.1 mM prevented the effects of pH...
  27. Akiba Y, Ghayouri S, Takeuchi T, Mizumori M, Guth P, Engel E, et al. Carbonic anhydrases and mucosal vanilloid receptors help mediate the hyperemic response to luminal CO2 in rat duodenum. Gastroenterology. 2006;131:142-52 pubmed
    ..The permeant carbonic anhydrase (CA) inhibitor methazolamide, relatively impermeant CA inhibitor benzolamide, vanilloid receptor antagonist capsazepine, or sodium-hydrogen exchanger 1 (NHE-1) inhibitor dimethyl amiloride ..
  28. Swenson E, Robertson H, Hlastala M. Effects of carbonic anhydrase inhibition on ventilation-perfusion matching in the dog lung. J Clin Invest. 1993;92:702-9 pubmed
    ..as a control for duration of anesthesia, (b) 4% CO2 inhalation to mimic systemic CO2 retention, (c) 1 mg/kg benzolamide (a selective renal CA inhibitor) or 0...
  29. Supuran C, Scozzafava A. Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. J Enzyme Inhib Med Chem. 2004;19:269-73 pubmed
    b>Benzolamide, an orphan drug belonging to the pharmacological class of sulfonamide carbonic anhydrase (CA, EC 4.2.1...
  30. Vullo D, Bhatt A, Mahon B, McKenna R, Supuran C. Sulfonamide inhibition studies of the α-carbonic anhydrase from the gammaproteobacterium Thiomicrospira crunogena XCL-2, TcruCA. Bioorg Med Chem Lett. 2016;26:401-405 pubmed publisher
    ..including acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, brinzolamide, benzolamide and benzenesulfonamides incorporating 4-hydroxyalkyl moieties...
  31. Leniger T, Wiemann M, Bingmann D, Widman G, Hufnagel A, Bonnet U. Carbonic anhydrase inhibitor sulthiame reduces intracellular pH and epileptiform activity of hippocampal CA3 neurons. Epilepsia. 2002;43:469-74 pubmed
    ..activity (induced by 50 microM 4-aminopyridine) were compared with those of the CA inhibitors acetazolamide and benzolamide. In the majority of neurons, sulthiame (1.0-1.5 mM; n = 8) as well as the membrane permeant acetazolamide (0...
  32. Kreitzer M, Swygart D, Osborn M, Skinner B, Heer C, Kaufman R, et al. Extracellular H+ fluxes from tiger salamander Müller (glial) cells measured using self referencing H+-selective microelectrodes. J Neurophysiol. 2017;:jn.00409.2017 pubmed publisher
    ..The carbonic anhydrase antagonist benzolamide potentiated the potassium-induced extracellular acidification, while 300 ?M DIDS, 300 ?M SITS and 30 ?M S0859 ..
  33. Akiba Y, Mizumori M, Kuo M, Ham M, Guth P, Engel E, et al. CO2 chemosensing in rat oesophagus. Gut. 2008;57:1654-64 pubmed publisher
    ..the cell-permeant carbonic anhydrase (CA) inhibitor methazolamide (MTZ, 1 mM), the cell-impermeant CA inhibitor benzolamide (BNZ, 0.1 mM), the transient receptor potential vanilloid 1 (TRPV1) antagonist capsazepine (CPZ, 0...
  34. Chen J, Chesler M. Modulation of extracellular pH by glutamate and GABA in rat hippocampal slices. J Neurophysiol. 1992;67:29-36 pubmed
    ..5. Superfusion of 10(-5)-10(-3) M acetazolamide acidified the baseline by 0.05-0.10 pH units and amplified the Schaffer collateral- and glutamate-evoked alkaline shifts.(ABSTRACT TRUNCATED AT 250 WORDS) ..