Furosemide,
abbreviated as FS, is a loop diuretic
drug with low solubility and permeability. Herein, three adducts derived
from FS and hexamethylenetetramine (HTEM), amantadine (AMD) and isonicotinic acid hydrazide
(INZ), including two salts (FS–HTEM and FS–AMD) and one
cocrystal (FS–INZ), have been readily
obtained. Single-crystal X-ray diffraction of three adducts revealed
similar layered structures but involving different hydrogen bonding
networks. The solubility of two salts is higher than the cocrystal,
and FS–HTEM has the highest solubility
among three adducts. The solubility of FS adducts is
influenced by anion–cation interactions, coformer, and hydrogen
bonds. The formation of carboxylic acid dimer and sulfonic acid dimer
in FS disfavors the solvation of the FS adducts.