Stable-Form Screening: Overcoming Trace Impurities That Inhibit Solution-Mediated Phase Transformation to the Stable Polymorph of Sulfamerazine

Gong, Yuchuan; Collman, Benjamin M.; Mehrens, Shawn; Lu, Enxian; Miller, Jonathan M.; Blackburn, A. C.; Grant, David J.W.

doi:10.1002/jps.21139

Cited by 38 publications

(33 citation statements)

References 13 publications

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“…Additive-induced polymorph preparation is a widespread approach. For example, a metastable polymorph of the antibacterial drug sulfamerazine was selectively crystallized in the presence of structurally related sulfonamide drugs such as additives, e.g., sulfamethazine, sulfadiazine, and N 4 -acetylsulfamerazine [33]. It was noted that a trace amount of N 4 -acetylsulfamerazine as impurity prevented solutionmediated phase transformation from Form I to Form II even after suspension for 2 weeks in acetonitrile.…”

Section: Additive-induced Polymorph Nucleationmentioning

confidence: 98%

Polymorphism in Molecular Crystals and Cocrystals

Aitipamula

2015

Advances in Organic Crystal Chemistry

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Polymorphism refers to a compound's ability to exist in more than one crystalline modification through variations in the solid-state structures. Over the years, polymorphism has received extensive academic and industrial attention because of its impact on physical and chemical properties of active pharmaceutical ingredients and materials. It is preferable to develop the most stable polymorph to avoid unwanted phase transformation during processing and manufacturing. Therefore, a thorough polymorph screening and complete characterization of all the polymorphs are vital for understanding stability and phase transformations among different polymorphs. Recent advances in screening methodologies and analytical techniques paved ways for successful identification of potential polymorphs. While polymorphism in active pharmaceutical ingredients and single-component crystals is widely studied, such studies in multicomponent crystals such as cocrystals have received significant attention only in recent years. This chapter highlights some recent polymorphic systems of molecular crystals and cocrystals and emphasizes the potential implications of polymorphism in pharmaceutical and materials science. A brief history of polymorphism, factors that control the crystallization of polymorphs, thermodynamic aspects, and recent advances in screening methodologies and analytical techniques are also covered.

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Section: Additive-induced Polymorph Nucleationmentioning

confidence: 98%

Polymorphism in Molecular Crystals and Cocrystals

Aitipamula

2015

Advances in Organic Crystal Chemistry

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“…7 It is well known that faster conversion in an SMPT process can be achieved by using a solvent with a greater solubility for the corresponding pharmaceutical compound. On the basis of our preliminary experiment, the acetonitrile content in our cosolvent was set to 85%.…”

Section: Smpt Processmentioning

confidence: 99%

“…A more detailed description can be found in the literature. 7 Sulfamerazine [SMZ, 4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide] has been prescribed as an antibacterial agent in combination with other antibiotics since the first report of its crystal structure as orthorhombic by X-ray diffraction (XRD) analysis. 8 The application of the SMPT process to SMZ was extensively studied and reported in a series of articles.…”

Section: Introductionmentioning

confidence: 99%

“…8 The application of the SMPT process to SMZ was extensively studied and reported in a series of articles. 7,9,10 Through a solubility study in various solvents substantiating the interfacial energy and the width of metastable zone, form II, the most stable polymorph of SMZ, was prepared via SMPT for the first time. 7 The nature of the phase transition between the two polymorphs (forms I and II) of SMZ was determined using microscopy, XRD, differential scanning calorimetry (DSC), and nuclear magnetic resonance.…”

Section: Introductionmentioning

confidence: 99%

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Quantitative In-Line Monitoring of Solvent-Mediated Polymorphic Transformation of Sulfamerazine by Near-Infrared Spectroscopy

Lee

Seo

Wang

et al. 2012

Journal of Pharmaceutical Sciences

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“…Solvents with high solubility (>8 mM) have been shown to provide the fastest slurry transformation rate to the stable form. 18,27,28 There are a few advantages in using higher temperature SMPT. Increasing temperature increases energy into the system allowing for increased molecular mobility and faster transformation rate.…”

Section: Measuring Accessible Desolvation Temperaturementioning

confidence: 99%