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

Lee, Min‐Jeong; Seo, Da-Young; Wang, In-Chun; Chun, Nan-Hee; Lee, Hea-Eun; Jeong, Myung-Yung; Kim, Woo‐Sik; Choi, Guang J.

doi:10.1002/jps.23042

Cited by 14 publications

(9 citation statements)

References 21 publications

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“…The main emphasis has been on the thermodynamics of the polymorph transformations and on mechanical properties such as millability, etc. (7,(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) Zhang et al reported that the thermodynamic transformation of Form II to Form I happens between 50-54 o C, (22) while in our previous work, we discovered that Form I goes to Form II on ball milling for an hour at room temperature. (8) Milling at low temperatures leads to the amorphization of both forms.…”

Section: Introductionmentioning

confidence: 85%

Sulfamerazine: Understanding the Influence of Slip Planes in the Polymorphic Phase Transformation through X-Ray Crystallographic Studies and ab Initio Lattice Dynamics

Pallipurath

Skelton

Warren³

et al. 2015

Mol. Pharmaceutics

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Understanding the polymorphism exhibited by organic active-pharmaceutical ingredients (APIs), in particular the relationships between crystal structure and the thermodynamics of polymorph stability, is vital for the production of more stable drugs and better therapeutics, and for the economics of the pharmaceutical industry in general. In this article, we report a detailed study of the structure-property relationships among the polymorphs of the model API, Sulfamerazine. Detailed experimental characterization using synchrotron radiation is complemented by computational modeling of the lattice dynamics and mechanical properties, in order to study the origin of differences in millability and to investigate the thermodynamics of the phase equilibria. Good agreement is observed between the simulated phonon spectra and mid-infrared and Raman spectra. The presence of slip planes, which are found to give rise to low-frequency lattice vibrations, explains the higher millability of Form I compared to Form II. Energy/volume curves for the three polymorphs, together with the temperature dependence of the thermodynamic free energy computed from the phonon frequencies, explains why Form II converts to Form I at high temperature, whereas Form III is a rare polymorph that is difficult to isolate. The combined experimental and theoretical approach employed here should be generally applicable to the study of other systems that exhibit polymorphism.

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Section: Introductionmentioning

confidence: 85%

Sulfamerazine: Understanding the Influence of Slip Planes in the Polymorphic Phase Transformation through X-Ray Crystallographic Studies and ab Initio Lattice Dynamics

Pallipurath

Skelton

Warren³

et al. 2015

Mol. Pharmaceutics

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“…FIII was discovered only recently in 2006 . Solvent‐mediated transformations of SMZ polymorphs in solution have been extensively studied . The effect of compression and milling on powder samples has also been reported .…”

Section: Introductionmentioning

confidence: 99%

“…29 Solvent-mediated transformations of SMZ polymorphs in solution have been extensively studied. [32][33][34][35][36][37][38] The effect of compression and milling on powder samples has also been reported. 30,[39][40][41] Chattoraj et al 39 observed partial amorphization of FI during cryomilling.…”

Section: Introductionmentioning

confidence: 99%

“…In particular, Raman and near‐infrared (NIR) spectroscopy in conjunction with multivariate analysis are now routinely used and are often the methods of choice because of their speed, nondestructive nature, and suitability for real‐time in situ analysis and minimal sample preparation and handling requirements . NIR spectroscopy combined with multivariate analysis has been used by Lee et al for the in‐line monitoring of the solvent‐mediated transformation of SMZ FI and FII. Analytical work on SMZ polymorphs has also been reported by Li et al who compared the effectiveness and accuracy of XRPD, Raman microscopy, and differential scanning calorimetry (DSC) for the quantitative analysis of binary mixtures of FI and FII.…”

Section: Introductionmentioning

confidence: 99%

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Effects of Ball-Milling and Cryomilling on Sulfamerazine Polymorphs: A Quantitative Study

MacFhionnghaile

Gniado

et al. 2014

Journal of Pharmaceutical Sciences

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The effects of ball-milling and cryomilling on sulfamerazine forms I and II (SMZ FI, FII) were investigated using X-ray powder diffraction, IR and NIR spectroscopy. Cryomilling resulted in the complete amorphization of both polymorphs. Milling at room temperature gave mixtures of amorphous SMZ (FA) and FII. Calibration models were developed for the quantitative analysis of binary (FI/FII, FI/FA and FII/FA) and ternary (FI/FII/FA) mixtures using NIR spectroscopy combined with partial least-squares (PLS) regression. The PLS models for binary (0 -100 %), ternary (0 -100 %) and low level (0 -10 %) binary mixtures had root-mean-square errors of prediction of 1.8, 5.1 and 0.80 %, respectively. The calibration models were used to obtain a detailed quantitative picture of solid-state transformations during milling and any subsequent recrystallizations. FA prepared by cryomilling FI for less than 60 min. recrystallized to mixtures of FI and FII, while samples milled for more than 60 min. crystallized to pure FII. The effect of co-milling SMZ with stoichiometric amounts of additives was investigated. SMZ formed amorphous materials with oxalic, DL-tartaric and citric acids that were more stable towards recrystallization than FA.Amorphous SMZ/oxalic acid was found to recrystallize to a 2:1 co-crystal during storage.

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“…PCA is a useful mathematical analysis method often used with PAT tools. It was applied to monitor polymorphic transformation , and to analyze crystallization process kinetics. , In contrast, DA is normally used for the classifying tasks . To confirm the composition of suspensions, the benchmark technique for crystal phase identification, i.e., PXRD, was employed to quantify the constituent solids in suspensions.…”

Section: Introductionmentioning

confidence: 99%

Online Classification of Mixed Co-Crystal and Solute Suspensions using Raman Spectroscopy

Sheng

Tan

2016

Org. Process Res. Dev.

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This work seeks to develop a calibration-free statistical approach based on Raman spectroscopy for on-line identification of impurities during co-crystallization. Caffeine-glutaric acidacetonitrile was employed as the model system, which forms co-crystals from solution at appropriate conditions. Raman spectra were collected in three classes of suspensions with a solid mixture of caffeine crystals and co-crystals, pure co-crystals, and a mixture of glutaric acid crystals and co-crystals, respectively at different temperatures. These suspensions were used to represent the possible products of co-crystallization processes during which single component could crystallize out concomitantly with the desired co-crystal. A statistical model combining principal component analysis (PCA) and discriminant analysis (DA) was developed to classify these suspensions. PCA was first performed for these spectra and the resulting first few principal components were subjected to DA. It was found that the three classes of suspensions can be distinguished clearly by DA.

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

Cited by 14 publications

References 21 publications

Sulfamerazine: Understanding the Influence of Slip Planes in the Polymorphic Phase Transformation through X-Ray Crystallographic Studies and ab Initio Lattice Dynamics

Sulfamerazine: Understanding the Influence of Slip Planes in the Polymorphic Phase Transformation through X-Ray Crystallographic Studies and ab Initio Lattice Dynamics

Effects of Ball-Milling and Cryomilling on Sulfamerazine Polymorphs: A Quantitative Study

Online Classification of Mixed Co-Crystal and Solute Suspensions using Raman Spectroscopy

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