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Related Experiment Videos

Ritonavir: an extraordinary example of conformational polymorphism.

J Bauer1, S Spanton, R Henry

  • 1Pharmaceutical Products Division, Abbott Laboratories, North Chicago, Illinois 60045, USA. john.f.bauer@abbott.com

Pharmaceutical Research
|July 28, 2001
PubMed
Summary
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Ritonavir exhibited conformational polymorphism, leading to supply issues due to a less soluble crystal form. Understanding these polymorphs is crucial for drug stability and formulation.

Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Pharmaceutical science

Background:

  • Norvir (ritonavir) semi-solid capsule supply was jeopardized by a new, less soluble crystal form.
  • Understanding ritonavir's solid-state properties is critical for pharmaceutical manufacturing and drug efficacy.

Purpose of the Study:

  • To characterize the two polymorphs of ritonavir.
  • To elucidate the structures and hydrogen bonding networks of each crystal form.
  • To investigate the cause of the sudden appearance of a less soluble polymorph.

Main Methods:

  • Solid-state Nuclear Magnetic Resonance (NMR) spectroscopy
  • Near Infrared (NIR) Spectroscopy
  • Powder X-ray Diffraction (PXRD)
  • Single crystal X-ray diffraction

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    • Main Results:

    • Detailed characterization and structure determination of ritonavir polymorphs.
    • Identification of an unusual conformation in form II, leading to a robust hydrogen bonding network.
    • Investigation into the heterogeneous nucleation mechanism of form II.

    Conclusions:

    • Ritonavir displays conformational polymorphism with two distinct crystal lattices possessing differing solubilities.
    • Form II, with a "cis" conformation, represents a more stable packing but is difficult to nucleate.
    • The sudden emergence of form II was attributed to a combination of high supersaturation and heterogeneous nucleation, likely by a degradation product.