Benzolamide

• CAT Number: I023259
• CAS Number: 3368-13-6
• Molecular Formula: C8H8N4O4S3
• Molecular Weight: 320.36
• Purity: 98%
• Synonyms: Benzolamide; CL 11366; CL-11366; CL11366; W 1803; W-1803; W1803.
• Target: Carbonic Anhydrase
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: 4°C, protect from light
• IUPAC Name: 1,3,4-Thiadiazole-2-sulfonamide, 5-((phenylsulfonyl)amino)-
• InChI: InChI=1S/C8H8N4O4S3/c9-18(13,14)8-11-10-7(17-8)12-19(15,16)6-4-2-1-3-5-6/h1-5H,(H,10,12)(H2,9,13,14)
• InChIKey: PWDGTQXZLNDOKS-UHFFFAOYSA-N
• SMILES: O=S(C1=NN=C(NS(=O)(C2=CC=CC=C2)=O)S1)(N)=O

Benzolamide (Cat No.:I023259) is a medication classified as a carbonic anhydrase inhibitor. It is primarily used to treat glaucoma, a condition characterized by increased intraocular pressure. By inhibiting the carbonic anhydrase enzyme, Benzolamide reduces the production of aqueous humor in the eye, thereby lowering pressure. This medication is available in oral or ophthalmic formulations and is often prescribed as an adjunctive treatment alongside other medications for glaucoma management.

Reference

1: González Arbeláez LF, Ciocci Pardo A, Swenson ER, Álvarez BV, Mosca SM, Fantinelli JC. Cardioprotection of benzolamide in a regional ischemia model: Role of eNOS/NO. Exp Mol Pathol. 2018 Oct 9;105(3):345-351. doi: 10.1016/j.yexmp.2018.10.003. [Epub ahead of print] PubMed PMID: 30308197.
2: Ciocci Pardo A, Díaz RG, González Arbeláez LF, Pérez NG, Swenson ER, Mosca SM, Alvarez BV. Benzolamide perpetuates acidic conditions during reperfusion and reduces myocardial ischemia-reperfusion injury. J Appl Physiol (1985). 2018 Aug 1;125(2):340-352. doi: 10.1152/japplphysiol.00957.2017. Epub 2017 Dec 21. PubMed PMID: 29357509.
3: Collier DJ, Wolff CB, Hedges AM, Nathan J, Flower RJ, Milledge JS, Swenson ER. Benzolamide improves oxygenation and reduces acute mountain sickness during a high-altitude trek and has fewer side effects than acetazolamide at sea level. Pharmacol Res Perspect. 2016 May 19;4(3):e00203. doi: 10.1002/prp2.203. eCollection 2016 Jun. PubMed PMID: 27433337; PubMed Central PMCID: PMC4876137.
4: Cecchi A, Winum JY, Innocenti A, Vullo D, Montero JL, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5775-80. PubMed PMID: 15501039.
5: Supuran CT, Scozzafava A. Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. J Enzyme Inhib Med Chem. 2004 Jun;19(3):269-73. PubMed PMID: 15499999.
6: Hempleman SC, Rodriguez TA, Bhagat YA, Begay RS. Benzolamide, acetazolamide, and signal transduction in avian intrapulmonary chemoreceptors. Am J Physiol Regul Integr Comp Physiol. 2000 Dec;279(6):R1988-95. PubMed PMID: 11080061.
7: Gottfried JA, Chesler M. Benzolamide inhibits low-threshold calcium currents in hippocampal pyramidal neurons. J Neurophysiol. 1995 Dec;74(6):2774-7. PubMed PMID: 8747235.
8: 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 Nov 1;488 ( Pt 3):767-77. PubMed PMID: 8576866; PubMed Central PMCID: PMC1156742.
9: Johanson CE. Differential effects of acetazolamide, benzolamide and systemic acidosis on hydrogen and bicarbonate gradients across the apical and basolateral membranes of the choroid plexus. J Pharmacol Exp Ther. 1984 Dec;231(3):502-11. PubMed PMID: 6094788.
10: Tucker BJ, Blantz RC. Studies on the mechanism of reduction in glomerular filtration rate after benzolamide. Pflugers Arch. 1980 Dec;388(3):211-6. PubMed PMID: 7193847.
11: Gennari FJ, Johns C, Caflisch CR. Effect of benzolamide on pH in the proximal tubules and peritubular capillaries of the rat kidney. Pflugers Arch. 1980 Aug;387(1):69-72. PubMed PMID: 6774315.
12: DuBose TD Jr, Pucacco LR, Seldin DW, Carter NW, Kokko JP. Microelectrode determination of pH and PCO2 in rat proximal tubule after benzolamide: evidence for hydrogen ion secretion. Kidney Int. 1979 Jun;15(6):624-9. PubMed PMID: 37362.
13: Hanson MA, Nye PC, Rao PS, Torrance RW. Effects of acetazolamide and benzolamide on the response of the carotid chemoreceptors to CQ2 [proceedings]. J Physiol. 1978 Nov;284:165P-166P. PubMed PMID: 731509.
14: Tucker BJ, Steiner RW, Gushwa LC, Blantz RC. Studies on the tubulo-glomerular feedback system in the rat. The mechanism of reduction in filtration rate with benzolamide. J Clin Invest. 1978 Nov;62(5):993-1004. PubMed PMID: 711863; PubMed Central PMCID: PMC371858.
15: Lang F, Quehenberger P, Greger R, Oberleithner H. Effect of benzolamide on luminal pH in proximal convoluted tubules of the rat kidney. Pflugers Arch. 1978 Jun 21;375(1):39-43. PubMed PMID: 28514.
16: Liddell NE, Maren TH. CO2 retention as a basis for increased toxicity of salicylate with acetazolamide: avoidance of increased toxicity with benzolamide. J Pharmacol Exp Ther. 1975 Oct;195(1):1-7. PubMed PMID: 241836.
17: Travis DM, Rolf LL, Berdick KA. Respiratory failure in oxygen-induced lung disease. A study of survival, development of hypoxemia, and response to benzolamide. Am Rev Respir Dis. 1972 Nov;106(5):740-51. PubMed PMID: 5078873.
18: Maren TH, Ellison AC. The teratological effect of benzolamide, a new carbonic anhydrase inhibitor. Johns Hopkins Med J. 1972 Feb;130(2):116-23. PubMed PMID: 5059470.
19: Kunau RT Jr. The influence of the carbonic anhydrase inhibitor, benzolamide (CL-11,366), on the reabsorption of chloride, sodium, and bicarbonate in the proximal tubule of the rat. J Clin Invest. 1972 Feb;51(2):294-306. PubMed PMID: 4621543; PubMed Central PMCID: PMC302127.
20: Broder LE, Oppelt WW. Effect of benzolamide on cerebrospinal fluid formation. J Pharmacol Exp Ther. 1969 Oct;169(2):271-6. PubMed PMID: 5824608.