Organic vapor sorption method of isostructural solvates and polymorph of tenofovir disoproxil fumarate

Jangmi Lee, Stephan X M Boerrigter, Young Woo Jung, Youngjoo Byun, Soon Hong Yuk, Stephen R. Byrn, Eun Hee Lee

Research output: Contribution to journalArticle

Abstract

Tenofovir disoproxil fumarate (TDF) is a prodrug of tenofovir that belongs to a class of antiretroviral drugs, a nucleotide reverse transcriptase inhibitor. An acetonitrile solvate of TDF I, another new solvated form of TDF, was prepared and solid state characterization of its form was conducted using powder X-ray diffraction, FT-IR spectroscopy, and organic vapor sorption isotherm. During the characterization work, it was discovered that (1) TDF I can form solvates and polymorph with a wide variety of organic solvents as well as water and (2) to different extents, these solvates undergoes anisotropic lattice contraction/expansion during desolvation/solvation process suggesting the formation of isostructural solvates of TDF. Solvents used in this study include ethanol, isopropyl alcohol, acetonitrile, cyclohexane, toluene, and water. Four new solvates using ethanol, isopropyl alcohol, acetonitrile, and toluene vapor and one polymorph using water vapor were discovered. Their solid state characterizations were conducted using powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and Fourier transform infrared spectroscopy. A variety of isostructural solvates and a polymorph of TDF was produced by an organic vapor sorption method, showing varying physicochemical properties. This study demonstrates an alternative crystallization method to obtain isostructural solvates.

Original languageEnglish (US)
Pages (from-to)253-262
Number of pages10
JournalEuropean Journal of Pharmaceutical Sciences
Volume50
Issue number3-4
DOIs
StatePublished - 2013
Externally publishedYes

Fingerprint

Tenofovir
2-Propanol
Toluene
X-Ray Diffraction
Powders
Ethanol
Reverse Transcriptase Inhibitors
Water
Differential Scanning Calorimetry
Steam
Prodrugs
Fourier Transform Infrared Spectroscopy
Crystallization
Spectrum Analysis

Keywords

  • Isostructural desolvate
  • Isostructural solvate
  • Solid-state characterization
  • Tenofovir disoproxil fumarate

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

Organic vapor sorption method of isostructural solvates and polymorph of tenofovir disoproxil fumarate. / Lee, Jangmi; Boerrigter, Stephan X M; Jung, Young Woo; Byun, Youngjoo; Yuk, Soon Hong; Byrn, Stephen R.; Lee, Eun Hee.

In: European Journal of Pharmaceutical Sciences, Vol. 50, No. 3-4, 2013, p. 253-262.

Research output: Contribution to journalArticle

Lee, Jangmi ; Boerrigter, Stephan X M ; Jung, Young Woo ; Byun, Youngjoo ; Yuk, Soon Hong ; Byrn, Stephen R. ; Lee, Eun Hee. / Organic vapor sorption method of isostructural solvates and polymorph of tenofovir disoproxil fumarate. In: European Journal of Pharmaceutical Sciences. 2013 ; Vol. 50, No. 3-4. pp. 253-262.
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