Absolute configuration and crystal packing for three chiral drugs prone to spontaneous resolution: Guaifenesin, methocarbamol and mephenesin

Solubility and Some Crystallization Properties of Conglomerate Forming Chiral Drug Guaifenesin in Water

“…All the diffraction patterns including samples with intermediate enantiomeric composition are superposed with the reference patterns and identical with the published diffraction patterns for rac ‐ 1 . The diffraction patterns also coincide with the theoretical one calculated according to single‐crystal X‐ray analysis data for guaifenesin . All these results reliably proof the formation of neither polymorphs nor crystal hydrates in the “diol 1 –water” system under the conditions studied.…”

“…Recently, based on the identity of the IR spectra of the racemic and scalemic crystalline samples, thermochemical studies, and X‐ray diffraction analysis, the conglomerate nature of rac ‐ 1 has been established . Also a separation procedure based on entrainment (i.e., preferential crystallization) of slightly enantiomerically enriched aqueous solution was introduced .…”

From racemic compounds through metastable to stable racemic conglomerates: crystallization features of chiral halogen and cyano monosubstituted phenyl glycerol ethers

“…This is indeed the case for X-ray studied conglomerates guaifenesin (1, R = CH 3 O) and mephenesin (1, R = CH 3 ). 8 Nevertheless, from other experience it follows that some stable conglomerate-forming compounds keep the conglomerate nature even after severe transformations of the hydroxyl-bearing fragments. Thus having no free OH groups, guaifenesin precursor 1,2-epoxy-3-(2-methoxyphenoxy)-propane 2, 9 and having a rather different set of hydrogen bond-forming fragments related to guaifenesin miorelaxant methocarbamol 3 8,10 both demonstrate the property of spontaneous resolution.…”

Ternary metal complexes of guaifenesin drug: Synthesis, spectroscopic characterization and in vitro anticancer activity of the metal complexes

“…Using these medicines in very young children might cause serious or possibly life threatening side effects. It is used to reduce chest congestion caused by the common cold, infections or allergies .It is quickly absorbed from the gastrointestinal tract, and is rapidly metabolized and excreted in the urine [3]. Guaifenesin is thought to act as an expectorant by increasing the volume and reducing the viscosity of secretions in the trachea and bronchi.…”