Distinct Conformations of Mirabegron Determined by MicroED

Adv Sci (Weinh). 2023 Dec;10(34):e2304476. doi: 10.1002/advs.202304476. Epub 2023 Oct 17.

Abstract

Mirabegron, commonly known as "Myrbetriq", has been widely prescribed as a medicine for overactive bladder syndrome for over a decade. However, the structure of the drug and what conformational changes it may undergo upon binding its receptor remain unknown. In this study, the authors employed microcrystal electron diffraction (MicroED) to reveal its elusive three-dimensional (3D) structure. They find that the drug adopts two distinct conformational states (conformers) within the asymmetric unit. Analysis of hydrogen bonding and packing demonstrated that the hydrophilic groups are embedded within the crystal lattice, resulting in a hydrophobic surface and low water solubility. Structural comparison revealed the presence of trans- and cis- forms in conformers 1 and 2, respectively. Comparison of the structures of Mirabegron alone with that of the drug bound to its receptor, the beta 3 adrenergic receptor (β3AR) suggests that the drug undergoes major conformational change to fit in the receptor agonist binding site. This research highlights the efficacy of MicroED in determining the unknown and polymorphic structures of active pharmaceutical ingredients (APIs) directly from powders.

Keywords: active pharmaceutical ingredient; conformer; crystallography; microcrystal electron diffraction (microed); mirabegron.

MeSH terms

  • Acetanilides
  • Adrenergic beta-3 Receptor Agonists / pharmacology
  • Electrons
  • Humans
  • Urinary Bladder, Overactive* / drug therapy

Substances

  • mirabegron
  • Adrenergic beta-3 Receptor Agonists
  • Acetanilides