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Molecular interactions in remdesivir-cyclodextrin systems.

Bianka Várnai1, Milo Malanga2, Tamás Sohajda2

  • 1Semmelweis University, Department of Pharmacognosy, Üllői út. 26, H-1085 Budapest, Hungary.

Journal of Pharmaceutical and Biomedical Analysis
|December 2, 2021
PubMed
Summary
This summary is machine-generated.

This study details the molecular interactions between Remdesivir (REM) and cyclodextrin (CD) derivatives, crucial for formulating COVID-19 therapies. Sulfobutylether-β-cyclodextrin (SBEβCD) significantly enhances REM

Keywords:
ComplexationNMRStability constantSulfobutylated-cyclodextrinVeklurypK(a) value

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Area of Science:

  • Pharmaceutical Sciences
  • Supramolecular Chemistry
  • Drug Formulation

Background:

  • Remdesivir (REM), an antiviral for COVID-19, exhibits poor water solubility, necessitating specialized formulation strategies.
  • Veklury™ (REM) formulation utilizes sulfobutylether-β-cyclodextrin (SBEβCD) as a solubilizing excipient under acidic conditions (pH 2).
  • Understanding the molecular interactions between REM and cyclodextrins (CDs) is vital for optimizing drug formulation and stability.

Purpose of the Study:

  • To elucidate the molecular-level interactions between Remdesivir (REM) and various cyclodextrin (CD) derivatives, including SBEβCD.
  • To experimentally determine the pKa of REM, a critical factor influencing its complexation with charged CDs.
  • To characterize the stability, stoichiometry, and structural aspects of REM-CD inclusion complexes.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy was extensively employed to study REM-CD systems.
  • UV-pH titration was used to experimentally determine the pKa of Remdesivir.
  • Proton NMR (¹H NMR) titrations and Job's method were utilized to quantify complex stability and stoichiometry.

Main Results:

  • The pKa of REM was determined to be 3.56, indicating a positive charge at the formulation pH of 2.0.
  • Complexes with β-cyclodextrin derivatives were significantly more stable (one order of magnitude) than those with γ-cyclodextrin derivatives.
  • Sulfobutylation of β-cyclodextrin (SBEβCD) substantially increased complex stability, with specific isomers showing high stability (logK = 4.35).

Conclusions:

  • The study provides the first comprehensive analysis of REM-CD complexation, revealing key structural determinants of stability.
  • The findings enable the rational design of novel CD derivatives with tailored properties for improved REM formulation, production, and analysis.
  • Understanding REM-CD interactions is crucial for developing effective and stable COVID-19 antiviral therapies.