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Salt screening and characterization for poorly soluble, weak basic compounds: case study albendazole.

G S Paulekuhn¹, J B Dressman, C Saal

¹Ciba Vision/Alcon, Gross-Wallstadt, Germany.

|August 9, 2013

Summary

Selecting the right salt form is crucial for drug development. This study characterized four albendazole salts, identifying the mesylate as having superior physicochemical properties for pharmaceutical applications.

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Area of Science:

Pharmaceutical Sciences
Solid-State Chemistry
Drug Discovery

Background:

Salt screening is vital for enhancing drug candidate properties in preclinical development.
Poorly soluble, weak basic compounds are common in drug discovery, necessitating salt form optimization.

Purpose of the Study:

To prepare and characterize four albendazole salts (hydrochloride, mesylate, sulfate, tosylate).
To evaluate the impact of different salt forms on physicochemical properties, including solubility and dissolution.
To identify an optimal salt form for further pharmaceutical development.

Main Methods:

Salt preparation and characterization using techniques like NMR, ion chromatography, and vibrational spectroscopy.
Solid-state analysis via SEM, XRPD, particle size distribution (PSD), BET surface area, and solid-state NMR.
Thermal analysis (TGA, DSC), hygroscopicity assessment (DVS, KFT), and solubility/dissolution studies in aqueous media.

Main Results:

Distinct differences in physicochemical behavior were observed among the albendazole salt forms.
Hygroscopicity varied significantly, with the sulfate form being the most hygroscopic and mesylate the least.
Dissolution rates were pH-dependent and improved for all salt forms compared to the free base, with mesylate showing promising performance.

Conclusions:

Extensive physicochemical characterization is essential for selecting the most suitable salt form for pharmaceutical development.
The albendazole mesylate salt demonstrated significantly improved physicochemical properties.
This study highlights the importance of salt selection in optimizing drug candidates like poorly soluble, weak bases.