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

Hee Jun Park, Min Soo Kim, Jeong Soo Kim, Wonkyung Cho, Junsung Park, Kwang Ho Cha, Young Shin Kang, Sung Joo Hwang

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Solid-state 13 C nuclear magnetic resonance ( 13 C- 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 13 C-SSNMR. 1 H T 1 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.

Original languageEnglish
Pages (from-to)1243-1247
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number9
DOIs
Publication statusPublished - 2010 Sep 1

Fingerprint

Molecular Conformation
Fluconazole
Polymorphism
Conformations
Dissolution
Carbon
Nuclear magnetic resonance
Propane
Triazoles
Chemical shift
Fourier Analysis
Relaxation time
Solubility
Raman scattering
Fourier transforms
Magnetic Resonance Spectroscopy
Infrared radiation
Recovery
Atoms
Experiments

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Park, Hee Jun ; Kim, Min Soo ; Kim, Jeong Soo ; Cho, Wonkyung ; Park, Junsung ; Cha, Kwang Ho ; Kang, Young Shin ; Hwang, Sung Joo. / Solid-state carbon NMR characterization and investigation of intrinsic dissolution behavior of fluconazole polymorphs, anhydrate forms I and II. In: Chemical and Pharmaceutical Bulletin. 2010 ; Vol. 58, No. 9. pp. 1243-1247.
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Solid-state carbon NMR characterization and investigation of intrinsic dissolution behavior of fluconazole polymorphs, anhydrate forms I and II. / Park, Hee Jun; Kim, Min Soo; Kim, Jeong Soo; Cho, Wonkyung; Park, Junsung; Cha, Kwang Ho; Kang, Young Shin; Hwang, Sung Joo.

In: Chemical and Pharmaceutical Bulletin, Vol. 58, No. 9, 01.09.2010, p. 1243-1247.

Research output: Contribution to journalArticle

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AU - Park, Hee Jun

AU - Kim, Min Soo

AU - Kim, Jeong Soo

AU - Cho, Wonkyung

AU - Park, Junsung

AU - Cha, Kwang Ho

AU - Kang, Young Shin

AU - Hwang, Sung Joo

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AB - Solid-state 13 C nuclear magnetic resonance ( 13 C- 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 13 C-SSNMR. 1 H T 1 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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