Synthesis and Characterization of Long-Acting Darunavir Prodrugs

Mol Pharm. 2020 Jan 6;17(1):155-166. doi: 10.1021/acs.molpharmaceut.9b00871. Epub 2019 Dec 3.

Abstract

Antiretroviral therapy (ART) has improved the quality of life in patients infected with HIV-1. However, complete viral suppression within anatomical compartments remains unattainable. This is complicated by adverse side effects and poor adherence to lifelong therapy leading to the emergence of viral drug resistance. Thus, there is an immediate need for cellular and tissue-targeted long-acting (LA) ART formulations. Herein, we describe two LA prodrug formulations of darunavir (DRV), a potent antiretroviral protease inhibitor. Two classes of DRV prodrugs, M1DRV and M2DRV, were synthesized as lipophilic and hydrophobic prodrugs and stabilized into aqueous suspensions designated NM1DRV and NM2DRV. The formulations demonstrated enhanced intracellular prodrug levels with sustained drug retention and antiretroviral activities for 15 and 30 days compared to native DRV formulation in human monocyte-derived macrophages. Pharmacokinetics tests of NM1DRV and NM2DRV administered to mice demonstrated sustained drug levels in blood and tissues for 30 days. These data, taken together, support the idea that LA DRV with sustained antiretroviral responses through prodrug nanoformulations is achievable.

Keywords: LASER ART; darunavir; long acting; prodrugs; protease inhibitors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CD4-Positive T-Lymphocytes / drug effects
  • CD4-Positive T-Lymphocytes / virology
  • Cell Survival / drug effects
  • Chromatography, Liquid
  • Darunavir / administration & dosage*
  • Darunavir / chemical synthesis
  • Darunavir / chemistry
  • Darunavir / pharmacokinetics
  • Drug Resistance, Viral / drug effects
  • HIV Protease Inhibitors / administration & dosage*
  • HIV Protease Inhibitors / pharmacokinetics
  • HIV-1 / drug effects
  • HIV-1 / enzymology
  • Humans
  • Macrophages / drug effects
  • Macrophages / ultrastructure
  • Macrophages / virology
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Microscopy, Electron
  • Prodrugs / administration & dosage*
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacokinetics
  • Rats
  • Tandem Mass Spectrometry

Substances

  • HIV Protease Inhibitors
  • Prodrugs
  • Darunavir