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The two solid state forms of the topically active antiandrogen cortexolone-17α-propionate useful in the treatment of skin disorders were fully characterized by several spectroscopic methods for monitoring and controlling pseudopolymorphism.A detailed investigation on the structural origin of Cortexolone-17α-propionate pseudopolymorphism is still missing.A combination of different spectroscopic data comparing the anhydrous and the hydrated forms are reported.Chemical, physical and spectral outcomes are useful starting point to develop a production process strictly standardized.Solid State NMR discriminates between the two pseudopolymorphs and might be applied for quantitative analysis.Cortexolone-17α-propionate (CP) is a topically active antiandrogen useful in the treatment of skin disorders. In the solid state, three anhydrous forms of this drug (CPI, CPII and CPIII) occur, together with one hydrated crystal (CPW). The single crystal structure of the monohydrated phase, CPW, compared with that of the anhydrous form CPIII, shows a markedly different solid state behavior. These latter pseudopolymorphic forms have also been fully characterized by spectroscopic methods.