title: Bumetanide--the way to its chemical structure.
abstract: 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.
mesh_terms: D001581:Benzothiadiazines; D002034:Bumetanide / Q000138:chemical synthesis*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D004232:Diuretics / Q000138:chemical synthesis* / Q000494:pharmacology; D005665:Furosemide / Q000138:chemical synthesis; D006801:Humans; D049993:Sodium Chloride Symporter Inhibitors / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
chemical_list: D001581:Benzothiadiazines; D002257:Carbonic Anhydrase Inhibitors; D004232:Diuretics; D049993:Sodium Chloride Symporter Inhibitors; D002034:Bumetanide; D005665:Furosemide