The integration of solid-form informatics into solid-form selection

J Pharm Pharmacol. 2015 Jun;67(6):857-68. doi: 10.1111/jphp.12394. Epub 2015 Apr 18.

Abstract

Objectives: To demonstrate how the use of structural informatics during drug development assists with the assessment of the risk of polymorphism and the selection of a commercial solid form.

Methods: The application of structural chemistry knowledge derived from the hundreds of thousands of crystal structures contained in the Cambridge Structural Database to drug candidates is described. Examples given show the comparison of intermolecular geometries to database-derived statistics, the use of Full Interaction Maps to assess polymorph stability and the calculation of hydrogen bond propensities to provide assurance of a stable solid form. The software tools used are included in the Cambridge Structural Database System and the Solid Form Module of Mercury.

Key findings: The early identification of an unusual supramolecular motif in the development phase of maraviroc led to further experimental work to find the most stable polymorph. Analyses of two polymorphs of a pain candidate drug demonstrated how consideration of molecular conformation and intermolecular interactions were used for the assessment of relative stability. Informatics analysis confirmed that the solid form of crizotinib, a monomorphic system, had a low risk of polymorphism.

Conclusions: The application of informatics-based assessment of new chemical entities complements experimental studies and provides a deeper understanding of the qualities of the structure. The information provided by structural analyses is incorporated into the assessment of risk. Informatics techniques are quick to apply and are straightforward to use, allowing an assessment of progressing drug candidates.

Keywords: Cambridge Structural Database; quality-by-design; solid-form informatics; solid-form selection.

MeSH terms

  • Analgesics / chemistry
  • Chemistry, Pharmaceutical*
  • Crizotinib
  • Crystallization
  • Cyclohexanes / chemistry
  • Databases, Factual
  • Drug Stability
  • Humans
  • Hydrogen Bonding
  • Informatics*
  • Maraviroc
  • Molecular Conformation
  • Pharmaceutical Preparations / chemistry*
  • Pyrazoles / chemistry
  • Pyridines / chemistry
  • Technology, Pharmaceutical*
  • Triazoles / chemistry

Substances

  • Analgesics
  • Cyclohexanes
  • Pharmaceutical Preparations
  • Pyrazoles
  • Pyridines
  • Triazoles
  • Crizotinib
  • Maraviroc