Transdermal Delivery of Metformin Utilizing Ionic Liquid Technology: Insight Into the Relationship Between Counterion Structures and Properties

Pharm Res. 2022 Oct;39(10):2459-2474. doi: 10.1007/s11095-022-03394-9. Epub 2022 Sep 28.

Abstract

Purpose: The purpose of the present study was to explore the feasibility of transdermal delivery of metformin, a commonly used oral antidiabetic drug, by ionic liquid (IL) technology.

Methods: Metformin hydrochloride (MetHCl) was first transformed into three kinds of ILs with different counterions. The physicochemical properties of the obtained ILs were characterized in depth. The simulation of stable configuration and calculation of interaction energies were conducted based on density functional theory (DFT). Skin-PAMPA was used to evaluate the intrinsic transdermal permeation properties. The cytotoxicity assay of these ILs was conducted using HaCaT cells to evaluate the toxicity to skin. These metformin ILs were then formulated into transdermal patch, and the transdermal potential was further evaluated using in vitro dissolution test and skin permeation assay. Finally, the pharmacokinetic profiles of these metformin IL-containing patches were determined.

Results: Among all the three Met ILs, metformin dihexyl sulfosuccinate (MetDH) with proper overall physiochemical and biological properties demonstrated the highest relative bioavailability. Metformin docusate (MetD) with the highest lipophilicity and intrinsic transdermal permeability exhibited the most significant sustained release profile in vivo. Both MetDH and MetD were the promising candidates for further clinical investigations.

Conclusions: Overall, the properties of ILs were closely related to the structures of counterion. IL technology provided the opportunities to finely tune the solid-state and biological properties of Metformin and facilitated the successful delivery by transdermal route.

Keywords: counterion structure; delivery system; ionic liquids; metformin; skin permeability; transdermal drug.

MeSH terms

  • Administration, Cutaneous
  • Delayed-Action Preparations
  • Dioctyl Sulfosuccinic Acid / metabolism
  • Hypoglycemic Agents / metabolism
  • Ionic Liquids* / chemistry
  • Ionic Liquids* / metabolism
  • Metformin*
  • Skin / metabolism
  • Skin Absorption
  • Transdermal Patch

Substances

  • Delayed-Action Preparations
  • Hypoglycemic Agents
  • Ionic Liquids
  • Dioctyl Sulfosuccinic Acid
  • Metformin