50357-46-5Relevant articles and documents
Preparation and characterisation of hexamidine salts
Parisi, Nicola,Matts, Paul J.,Lever, Rebecca,Hadgraft, Jonathan,Lane, Majella E.
, p. 404 - 411 (2015)
Hexamidine diisethionate (HEX D) has been used in the personal care industry and in a number of over-the-counter (OTC) drug products as an antimicrobial agent since the 1950's. Recently, the compound has also been investigated for its beneficial effects on skin health. Surprisingly, there is only limited information describing the physicochemical properties of this compound in the literature. The objective of this work was therefore to conduct a comprehensive programme of characterisation of HEX D as well as its dihydrochloride salt (HEX H). HEX H was prepared from HEX D by a simple acid addition reaction. Both salts were characterised using Nuclear Magnetic Resonance (NMR), Differential scanning calorimetry (DSC), and Thermogravimetric analysis (TGA). A new high performance liquid chromatographic method was developed and validated for both compounds. The pH in aqueous solution as well as respective distribution coefficients between octanol and pH 7.4 buffer were also determined. Finally, solubility and short term stability studies were conducted in a range of solvents. NMR analysis confirmed the preparation of HEX H from HEX D. Thermal analysis indicated the melting points of HEX D and HEX H were 225 °C and 266 °C respectively. HPLC analysis confirmed the purity of both salts. Log D values at pH 7.4 were -0.74 for HEX D and -0.70 for HEX H respectively. The physicochemical properties of two HEX salts have been established using a range of analytical approaches. Detailed solubility and stability data have also been collated. This information will be useful in the design of novel formulations for targeted delivery of these compounds to the skin.
