[Structure-activity relationships in the diuretic xipamide (4-chloro-5-sulfamoyl-2', 6' -salicyloxylidide)].
The synthesis of various derivatives of 4-chlorosalicylic acid substituted in position 5 is described.  The evaluation of their diuretic potency on the rat showed 4-chloro-5-sulfamoyl-2,6-salicyloxylidide (BE 1293, xipamide, Aquaphor) as the most effective one.  The normal urinary volume is increased tenfold by a oral dose of 100 mg/kg body weight.  All changes in the molecular structure of xipamide, even acetylation, the introduction of a second sulfamoyl group or the exchange of the sulfonic group for the carbonyl group, lead to a decrease in activity.
D000107:Acetylation; D000818:Animals; D004231:Diuresis / Q000187:drug effects; D004232:Diuretics / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D008745:Methylation; D051381:Rats; D012457:Salicylamides / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013449:Sulfonamides; D014992:Xylenes / Q000032:analysis / Q000138:chemical synthesis / Q000494:pharmacology
D004232:Diuretics; D012457:Salicylamides; D013449:Sulfonamides; D014992:Xylenes
Struktur-Wirkungsbeziehungen beim Diuretikum Xipamid (4-Chlor-5-sulfamoyl-2',6'-salicyloxylidid)