Stabilization technology of glass structures is of great interest in the field of pharmaceutical science, as it may prevent poorly soluble candidate compounds from dropping out of the pipeline. Cooling rate from the melt has been recognized as one parameter to alter the energy state of the glass; however, the relationship between the physicochemical properties of glass and stabilization efficiency of the cooling rate has not been clarified yet. We have investigated the effect of cooling rate on the thermodynamic parameters of 13 pharmaceutical glasses, to find features of the compounds that are closely related to the stabilization efficiency. We have also analyzed the structural differences between slowly cooled and annealed glasses based on Fourier-transform infrared spectra and relaxation enthalpy. Although the degree of stabilization was lower for slowly cooled glasses compared to that for vapor-deposited ones, slow cooling was found to be a prominent method for producing stable glass and is applicable to bulk materials. In this observation, a strong correlation between fragility and the number of rotatable bonds was also found.