Design and molecular insights of drug-active metabolite based co-amorphous formulation: A case study of toltrazuril-ponazuril co-amorphous

Int J Pharm. 2022 Mar 5:615:121475. doi: 10.1016/j.ijpharm.2022.121475. Epub 2022 Jan 15.

Abstract

Co-amorphous supersaturated drug delivery systems are emerging as an alternative strategy to improve the water solubility of BCS II drugs. Typically, the supersaturation and stability of co-amorphous systems largely depend on the type of employed co-former. This study aims to assess the potential for active metabolites of drugs as co-former in drug-drug co-amorphous formulations. Toltrazuril (Tol) was chosen as the model drug, to which ponazuril (Pon) was added as co-former. Considering the importance of intermolecular interactions in co-amorphous systems, we performed highlighted investigations including molecular dynamics simulation and quantum mechanics calculations. The results indicated that Tol and Pon molecules were connected by N-H···O = C hydrogen bonds in the form of a complementary pairing of amide groups. Further, the solubility/dissolution and solid-state stability of the co-amorphous system were investigated. We found that co-amorphous Tol-Pon was stable for at least one month at 40 °C/75% RH, while amorphous materials underwent recrystallization within 10 days. Moreover, both drugs in the co-amorphous system exhibited enhanced "spring parachute effect" during the dissolution process. This could be attributed to the noticeably increased solid-state stabilization as well as inhibition of Pon on the crystallization of Tol from a supersaturated state. In general, our study provides some useful information and molecular insights to guide the development of drug-active metabolite-based co-amorphous formulations.

Keywords: Co-amorphization; Dissolution; Hydrogen bonding; Molecular simulation; Stability; Toltrazuril.

MeSH terms

  • Drug Stability
  • Pharmaceutical Preparations*
  • Solubility
  • Triazines

Substances

  • Pharmaceutical Preparations
  • Triazines
  • ponazuril
  • toltrazuril