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From a binary salt to salt co‐crystals of antibacterial agent lomefloxacin with improved solubility and bioavailability
Author(s) -
Zhang ZhiHui,
Zhang Qi,
Zhang QingQing,
Chen Chen,
He MingYang,
Chen Qun,
Song GuoQiang,
Xuan XiaoPeng,
Huang XianFeng
Publication year - 2015
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520615011191
Subject(s) - lomefloxacin , hydrogen bond , solubility , ternary operation , salt (chemistry) , supramolecular chemistry , chemistry , stacking , crystallography , molecule , inorganic chemistry , materials science , crystal structure , organic chemistry , norfloxacin , biochemistry , ciprofloxacin , computer science , programming language , antibiotics
The cocrystallization of lomefloxacin (Lf) with barbituric acid (HBA) and/or isophthalic acid (H 2 ip) leads to novel binary and ternary salts via hydrogen‐bonding recognition. X‐ray single‐crystal diffraction analyses show that zwitterionic lomefloxacin can adjust itself to fulfill a different supramolecular array in either binary salts or ternary salt co‐crystals, formulated as [HLf]·[Hip]·H 2 O (1), [HLf]·[BA]·[HBA]·H 2 O (2) and [HLf]·[BA]·[H 2 ip]·CH 3 OH·H 2 O (3). These pharmaceutical agents present uniform charge‐assisted hydrogen‐bonding networks between HLf cations and acidic coformers with the lattice capturing water molecules. Structural comparison of (2) and (3) indicated that a delicate balance of geometries and hydrogen‐bonding partners is required for stacking to favor the formation of ternary salt co‐crystals. Cocrystallization was able to overcome the water insolubility of lomefloxacin. Both the salt co‐crystals display enhanced solubility and better pharmaceutical applicability.