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The aims of this study were to examine the phase behavior of itraconazole–phenol mixtures and assess the feasibility of topical formulations of itraconazole using eutectic mixture systems. Itraconazole–phenol eutectic mixtures were characterized using differential scanning calorimetry, Fourier transform infrared spectroscopy, 1H-nuclear magnetic resonance, and powder X-ray diffractometry. The skin permeation rates of itraconazole–phenol eutectic formulations were determined using Franz diffusion cells fitted with excised hairless mouse skins. Itraconazole can form eutectic compounds with phenol, and the hydrogen-bonding interactions between the carbonyl group in the itraconazole and hydroxyl group in phenol play a major role in itraconazole–phenol eutectic formation. Despite its high molecular weight and hydrophobicity, the drug (i.e., itraconazole) can be permeated through excised hairless mouse skins from itraconazole–phenol eutectic formulations. The findings of this study emphasize the capabilities of the topical application of itraconazole via external preparations.