Full spectroscopic characterization of two crystal pseudopolymorphic forms of the antiandrogen cortexolone 17α-propionate for topic application

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. [Display omitted] •A detailed investigation on the structur...

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Published in:	Steroids Vol. 128; pp. 95 - 104
Main Authors:	Ferraboschi, Patrizia, Chiara Sala, Maria, Stradi, Riccardo, Ragonesi, Laura, Gagliardi, Clarissa, Lanzarotti, Paolo, Ragg, Enzio M., Mori, Matteo, Meneghetti, Fiorella
Format:	Journal Article
Language:	English
Published:	United States Elsevier Inc 01-12-2017
Subjects:	Administration, Topical Androgen Antagonists - chemistry Androgen Antagonists - therapeutic use Cortodoxone - analogs & derivatives Cortodoxone - chemistry Cortodoxone - therapeutic use Crystallization Humans Magnetic Resonance Spectroscopy Propionates - chemistry Propionates - therapeutic use Skin Diseases - drug therapy Solid-state NMR spectroscopy Solvopolymorphism Steroidal hormone X-Ray Diffraction X-ray diffractometry Solvopolymorphism Solid-state NMR spectroscopy Steroidal hormone X-ray diffractometry
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Summary:	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. [Display omitted] •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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0039-128X 1878-5867
DOI:	10.1016/j.steroids.2017.09.003