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Related Concept Videos

Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism01:21

Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism

Polymorphism refers to the existence of a drug substance in multiple crystalline forms, known as polymorphs. Recently, this term has been expanded to include solvates (forms containing a solvent), amorphous forms (non-crystalline forms), and desolvated solvates (forms from which the solvent has been removed).
Some polymorphic crystals possess lower aqueous solubility than their amorphous counterparts, leading to incomplete absorption. For instance, the oral suspension of Chloramphenicol, which...
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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
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Changes in polymorphic forms can significantly influence the bioavailability of poorly soluble drugs. Although the FDA defines pharmaceutical equivalence based on having the same active ingredient, dosage form, and route of administration, it does not automatically disqualify products with different polymorphic forms. This means two products with different polymorphs can still be deemed pharmaceutically equivalent. However, polymorphic differences can affect properties like wettability,...
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Unlike ionic or small covalent molecules, polymers do not form crystalline solids due to the diffusion limitations of their long-chain structures. However, polymers contain microscopic crystalline domains separated by amorphous domains.
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Application and Methodology of the Non-destructive 19F Time-domain NMR Technique to Measure the Content in Fluorine-containing Drug Products
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Nonamorphism in flufenamic acid and a new record for a polymorphic compound with solved structures.

Vilmalí López-Mejías1, Jeff W Kampf, Adam J Matzger

  • 1Department of Chemistry and the Macromolecular Science and Engineering Program, University of Michigan-Ann Arbor, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.

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|June 14, 2012
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Flufenamic acid (FFA), a non-steroidal anti-inflammatory drug (NSAID), exhibits unprecedented polymorphism. Researchers successfully synthesized nine distinct crystalline forms, confirming FFA as octamorphic and highlighting the complex factors influencing its phase selection.

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Area of Science:

  • Materials Science
  • Crystallography
  • Pharmaceutical Science

Background:

  • Polymorphism, the ability of a solid material to exist in multiple crystalline forms, significantly impacts drug properties.
  • Flufenamic acid (FFA), a non-steroidal anti-inflammatory drug (NSAID), was previously known to have limited crystalline forms.
  • Understanding FFA's polymorphism is crucial for its pharmaceutical development and efficacy.

Purpose of the Study:

  • To investigate and characterize the extensive polymorphism of flufenamic acid (FFA).
  • To explore novel methods for accessing and elucidating different crystalline forms of FFA.
  • To understand the kinetic factors governing FFA's crystallization and phase selection.

Main Methods:

  • Utilized polymer-induced heteronucleation (PIHn) to induce crystallization.
  • Employed solid-solid transformation techniques at low temperatures.
  • Performed structural elucidation of the obtained crystalline forms using advanced analytical techniques.

Main Results:

  • Successfully accessed nine distinct polymorphs of flufenamic acid (FFA).
  • Confirmed FFA as octamorphic, with six newly characterized forms in addition to two previously known.
  • Observed the co-occurrence of multiple polymorphs under a single PIHn condition, indicating complex crystallization kinetics.

Conclusions:

  • Flufenamic acid (FFA) displays remarkable and unprecedented polymorphism.
  • Polymer-induced heteronucleation (PIHn) is an effective strategy for accessing diverse FFA polymorphs.
  • The phase selection of FFA is governed by a complex interplay of kinetic factors during crystallization.