Enantiotropically related albendazole polymorphs

Journal of Pharmaceutical Sciences
M B PranzoR Bettini

Abstract

In the present study we report the solid-state properties of albendazole (ABZ) re-crystallized from different solvents for comparison with the commercially available form. Crystalline phases were characterized as to thermal behavior, X-ray diffractometry, both on powder and single crystal, and solubility in methanol or 0.1 N HCl. The relevant thermodynamic parameters were calculated from solubility measurements at different temperatures. The re-crystallization of ABZ both from methanol and N,N-dimethylformamide afforded a new stable polymorph form (Form II) enantiotropically related to the commercially available ABZ (Form I), the latter being the metastable form at ambient temperature. Both forms proved to be physically quite stable, likely due to a high-energy barrier for the activation of the interconversion. ABZ in the solid state represents a rather complex system in which the molecular structural differences that could be associated with the polymorphism are of at least four possible types, or combinations of these: (a) tautomeric; (b) different conformations of either or both of the side-chains attached to the bicyclic ring system; (c) the occurrence of molecular disorder or its absence; (d) no essential difference in mol...Continue Reading

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Citations

Aug 28, 2012·Pharmaceutical Research·Blair Kathryn BrettmannBernhardt L Trout
Feb 22, 2012·Journal of Pharmaceutical Sciences·Pratik UpadhyayArvind K Bansal
Oct 13, 2011·Journal of Pharmaceutical Sciences·Harry G Brittain
Jan 16, 2016·International Journal of Pharmaceutics·Laura Martinez-MarcosGavin W Halbert
Jun 28, 2014·International Journal of Pharmaceutics·Franco PattarinoLorella Giovannelli
Apr 7, 2015·Carbohydrate Polymers·M João G FerreiraTeresa G Nunes
Aug 5, 2016·Journal of Pharmaceutical Sciences·Henrik PalmelundThomas Rades
Jul 19, 2016·Journal of Pharmaceutical and Biomedical Analysis·Natalia L CalvoTeodoro S Kaufman
Aug 23, 2012·Organic & Biomolecular Chemistry·Jennifer R HiscockNeil J Wells
Jan 29, 2019·Artificial Cells, Nanomedicine, and Biotechnology·Faheem MaqboolJames R Falconer
Dec 30, 2014·Journal of Microencapsulation·Lisa ElviriRuggero Bettini
Jan 26, 2021·Drug Development and Industrial Pharmacy·Monica R P RaoTejal Gangwal
Nov 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Roxana RacoviceanuCodruţa Şoica

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