Bumetanide--the way to its chemical structure

• Published in: Journal of clinical pharmacology Vol. 21; no. 11; p. 531
• Main Author: Feit, P W
• Format: Journal Article
• Language: English
• Published: England 01.11.1981
• Subjects: Benzothiadiazines; Bumetanide - chemical synthesis; Carbonic Anhydrase Inhibitors - chemical synthesis; Chemical Phenomena; Chemistry; Diuretics - chemical synthesis; Diuretics - pharmacology; Furosemide - chemical synthesis; Humans; Sodium Chloride Symporter Inhibitors - chemical synthesis; Structure-Activity Relationship
• ISSN: 0091-2700
• DOI: 10.1002/j.1552-4604.1981.tb05661.x

The steps in the evolution of sulfamoyl diuretics in current clinical use are outlined. The development was initiated by the chance observation of a clinical side effect of sulfanilamide, which became the first sulfamoyl group (-SO2NH2)-bearing compound used for diuretic treatment of patients. Ensuing chemical synthesis over the past three decades led to the development of three types of sulfamoyl diuretics:carbonic anhydrase inhibitors, thiazides, and the loop or high-ceiling saluretic agents represented by furosemide and bumetanide. The structural relationship of furosemide to sulfanilamide and the thiazide-type diuretics and, for bumetanide, the more specific structure for loop diuretic activity are discussed.