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Sorafenib and its tosylate salt: a multikinase inhibitor for treating cancer

K Ravikumar1, B Sridhar, A K S Bhujanga Rao

  • 1Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sshiya@yahoo.com

Acta Crystallographica. Section C, Crystal Structure Communications
|January 6, 2011
PubMed

Insights

Sorafenib, a cancer drug, was crystallized as a free base and a tosylate salt. Its solid-state conformation varies depending on the crystalline environment, differing from enzyme-bound forms.

Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Solid-State Chemistry

Background:

  • Sorafenib is a targeted therapy drug crucial for treating various cancers by inhibiting tumor angiogenesis.
  • Understanding the solid-state properties of drugs like sorafenib is essential for formulation and efficacy.

Purpose of the Study:

  • To investigate and characterize the crystal structures of sorafenib free base and its tosylate salt.
  • To analyze the conformational variations of sorafenib in different crystalline environments.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structures.
  • Analysis of hydrogen bonding and intermolecular interactions within the crystal lattices.

Main Results:

  • Sorafenib was successfully crystallized as both a free base (I) and a tosylate salt (II).
  • The molecule adopted an extended conformation in both crystal forms.
  • Significant differences in the conformation of the pyridine-2-carboxamide group and terminal rings were observed compared to enzyme-bound sorafenib.
  • Distinct hydrogen bonding patterns were identified: zigzag chains in the free base and fused rings in the tosylate salt.

Conclusions:

  • The solid-state conformation of sorafenib is sensitive to its crystalline environment.
  • These structural insights are vital for understanding sorafenib's physical properties and potential for drug formulation.

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