Solid-state carbon NMR characterization and investigation of intrinsic dissolution behavior of fluconazole polymorphs, anhydrate forms 1 and 2

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  • Park Hee Jun
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Kim Min-Soo
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Kim Jeong-Soo
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Cho Wonkyung
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Park Junsung
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Cha Kwang-Ho
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Kang Young-Shin
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University
  • Hwang Sung-Joo
    Center for Nanotechnology-Based New Drug Dosage Form, College of Pharmacy, Chungnam National University

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  • Solid-State Carbon NMR Characterization and Investigation of Intrinsic Dissolution Behavior of Fluconazole Polymorphs, Anhydrate Forms I and II

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Solid-state 13C nuclear magnetic resonance (13C-SSNMR) revealed significant differences in the chemical shift of specific carbon atoms between two fluconazole polymorphs, reflecting a change in molecular conformation. A single resonance signal without splitting was observed in the spectrum of anhydrate form II, while the spectrum of anhydrate form I showed signals with splitting, indicating the presence of two dissimilar molecular conformations in the unit cell of anhydrate form I. The Fourier transform infrared (FT-IR) and Raman spectra associated with the triazole group, the 2,4-difluorobenzyl group, and the propane backbone provided also evidence of structural differences between forms I and II accompanying with 13C-SSNMR. 1H T1 relaxation times, measured using saturation recovery experiments, showed that the metastable anhydrate form II was more mobile than the stable form I. The solubility and intrinsic dissolution tests showed that the anhydrate form II was more soluble and dissolved faster than the anhydrate form I.

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