Cocrystallization of Trimethoprim and Solubility Enhancement via Salt Formation

Qixuan Zheng, Daniel K. Unruh, Kristin M. Hutchins

Research output: Contribution to journalArticlepeer-review

Abstract

Trimethoprim (TMP) is an active pharmaceutical ingredient with poor aqueous solubility. Here, we describe the cocrystallization of TMP with five co-formers, three bipyridines and two monopyridines. Cocrystallization of TMP with the bipyridines yields neutral cocrystals, and while both components are present in the lattice, they do not interact with each other via any strong intermolecular forces. Conversely, cocrystallization of TMP with the monopyridines yields salts, and included water or solvent molecules that play a key role in supramolecular assembly. Moreover, the salts exhibit significantly higher aqueous solubility than that of TMP. Two solids feature a compound on the Generally Recognized as Safe list, making them promising as ionic pharmaceutical cocrystals.

Original languageEnglish
Pages (from-to)1507-1517
Number of pages11
JournalCrystal Growth and Design
Volume21
Issue number3
DOIs
StatePublished - Mar 3 2021

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