Rotigotine: Unexpected Polymorphism with Predictable Overall Monotropic Behavior

Journal of Pharmaceutical Sciences
Ivo B Rietveld, René Céolin

Abstract

Crystallization of polymorphs still has a touch of art, as even prior observations of polymorphs do not guarantee their crystallization. However, once crystals of various polymorphs have been obtained, their relative stabilities can be established with a straightforward thermodynamic approach even if the conclusion will depend on the quality of the experimental data. Rotigotine is an active pharmaceutical ingredient, which has suffered the same setback as Ritonavir: a sudden appearance of a more stable crystalline polymorph than the one used for the formulation. Although the cause of the defect in the formulation was quickly established, the interpretation of the phase behavior of rotigotine has been lacking in clarity. In the present paper, data published in the patents resulting from the discovery of the new polymorph have been used to establish the pressure-temperature phase diagram of the two known solid forms of rotigotine. The analysis clearly demonstrates that form II is the stable solid phase and form I is metastable in the entire pressure-temperature domain: form I is overall monotropic in relation to form II. Thus, it was a sensible decision of European Medicines Agency to ask for a reformulation, as the first formula...Continue Reading

References

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Nov 6, 2007·International Journal of Pharmaceutics·P BennemaH Meekes
Nov 4, 2008·Expert Opinion on Drug Delivery·K Ray Chaudhuri
Jul 21, 2009·Acta Crystallographica. Section B, Structural Science·Eric J ChanT Richard Welberry
May 23, 2013·Journal of Pharmaceutical Sciences·Marc-Antoine PerrinIvo B Rietveld
Sep 3, 2013·International Journal of Pharmaceutics·Inès GanaIvo B Rietveld
Sep 1, 2014·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Donald A McAfeeMajella E Lane

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Citations

Jul 6, 2016·International Journal of Pharmaceutics·Théo HenrietIvo B Rietveld
Jan 23, 2017·Journal of Pharmaceutical Sciences·Bram HarmsenTom Leyssens
Jul 25, 2018·Faraday Discussions·Jonas Nyman, Susan M Reutzel-Edens
Sep 12, 2018·Physical Chemistry Chemical Physics : PCCP·Béatrice NicolaïIvo B Rietveld
Mar 17, 2020·Current Pharmaceutical Design·Shadab MdNabil A Alhakamy
Oct 20, 2018·Proceedings. Mathematical, Physical, and Engineering Sciences·Sarah L Price
Oct 27, 2020·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Scott M WoodleyR Catlow
Dec 7, 2020·International Journal of Pharmaceutics·Ivo B RietveldJosep-Lluís Tamarit
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea ScarperiMarco Geppi
Jun 28, 2019·Chemical Reviews·Robin Taylor, Peter A Wood
Sep 4, 2020·The Journal of Physical Chemistry. a·Olga EgorovaGraeme M Day

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