Metastable crystal growth of acetaminophen using solution-mediated phase transformation

Mori, Yojiro; Maruyama, Mihoko; Takahashi, Yoshinori; Yoshikawa, Hiroshi; Okada, Shino; Adachi, Hiroaki; Sugiyama, Shigeru; Takano, Kazufumi; Murakami, Satoshi; Matsumura, Hideki; Inoue, Tsuyoshi; Yoshimura, Masashi; Mori, Yusuke

doi:10.7567/apex.10.015501

Cited by 20 publications

(17 citation statements)

References 27 publications

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“…By this cycle, the transformation from COD to COM will gradually proceed. The solution-mediated transformation from a metastable phase to the stable phase often occurs in other materials[26–28]. Finally, the mosaic texture composed of irregular-oriented COM crystals appears from the center part of the kidney stone (Fig2.…”

Section: Discussionmentioning

confidence: 99%

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

Maruyama

Sawada

Tanaka

et al. 2022

Preprint

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We aimed to identify and quantitatively analyze calcium oxalate (CaOx) kidney stones on the order of micrometers, with a focus on the quantitative identification of calcium oxalate monohydrate (COM) and dihydrate (COD). Fourier Transform Infrared (FTIR) spectroscopy, powder X-ray diffraction (PXRD), and microfocus X-ray CT measurements (micro-CT) were performed, and the results were compared. The extended analysis method of the FTIR spectrum, focusing on the 780 cm−1peak, made it possible to achieve a reliable analysis of the COM/COD ratio. We succeeded in the quantitative analysis of COM/COD in the region of 50 × 50 μm by microscopic FTIR for thin sections of kidney stones, and by the micro-CT for bulk samples. The extended analysis method of the FTIR spectrum focusing on the 780 cm−1peak was introduced to analyze the COM/COD ratio. The analysis results based on PXRD measurement with micro sampling, microscopic FTIR analysis of a thin section, and micro-CT observation of a bulk sample of a kidney stone showed roughly consistent results, indicating that all methods can be used complementarily. This quantitative analysis method evaluates the detailed CaOx composition on the preserved stone surface and provides information on the stone formation processes and interactions with organic molecules.

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Section: Discussionmentioning

confidence: 99%

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

Maruyama

Sawada

Tanaka

et al. 2022

Preprint

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Section: Selective Crystallization Methodsmentioning

confidence: 99%

“…Later, Mori et al 107 were able to isolate form II by solutionmediated phase transformation from a trihydrate of paracetamol, which is less stable than form II. The procedure consisted of placing seeds of form II in a saturated solution of paracetamol containing crystals of trihydrate, and letting the seeds of form II grow at the expense of the dissolving crystals of trihydrate (Figure 12).…”

Section: Organic Process Research and Developmentmentioning

confidence: 99%

Application of Selective Crystallization Methods To Isolate the Metastable Polymorphs of Paracetamol: A Review

Cruz

Rocha

Ferreira

2019

Org. Process Res. Dev.

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Paracetamol is a popular antipyretic and analgesic active pharmaceutical ingredient that is used worldwide in the production of several millions of tablets and other dosage forms every year. Paracetamol has three fully characterized polymorphs (forms I, II, and III), and also two high pressure polymorphs with unknown crystal structure (forms IV and V). Form I is the most stable polymorph, but unfortunately, it is not appropriate for direct compression into tablets due to its weak compression properties. On the other hand, forms II and III exhibit better compression properties; however, they are more difficult to harvest and isolate. This has been motivating the development of a diversity of crystallization methods that allow the selective production of forms II and III of paracetamol, which includes crystallization from melts, crystallization from liquid solutions, application of high pressures, seeding, heterogeneous nucleation, contact line crystallization, reaction coupling, ultrasound assisted crystallization, and multicomponent crystallization. In this review, we present a brief description of these methods and summarize their main advantages and disadvantages.

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Section: Plos Onementioning

confidence: 99%

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

et al. 2023

Self Cite

View full text Add to dashboard Cite

We sought to identify and quantitatively analyze calcium oxalate (CaOx) kidney stones on the order of micrometers, with a focus on the quantitative identification of calcium oxalate monohydrate (COM) and dihydrate (COD). We performed Fourier transform infrared (FTIR) spectroscopy, powder X-ray diffraction (PXRD), and microfocus X-ray computed tomography measurements (microfocus X-ray CT) and compared their results. An extended analysis of the FTIR spectrum focusing on the 780 cm−1 peak made it possible to achieve a reliable analysis of the COM/COD ratio. We succeeded in the quantitative analysis of COM/COD in 50-μm2 areas by applying microscopic FTIR for thin sections of kidney stones, and by applying microfocus X-ray CT system for bulk samples. The analysis results based on the PXRD measurements with micro-sampling, the microscopic FTIR analysis of thin sections, and the microfocus X-ray CT system observation of a bulk kidney stone sample showed roughly consistent results, indicating that all three methods can be used complementarily. This quantitative analysis method evaluates the detailed CaOx composition on the preserved stone surface and provides information on the stone formation processes. This information clarifies where and which crystal phase nucleates, how the crystals grow, and how the transition from the metastable phase to the stable phase proceeds. The phase transition affects the growth rate and hardness of kidney stones and thus provides crucial clues to the kidney stone formation process.

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Metastable crystal growth of acetaminophen using solution-mediated phase transformation

Cited by 20 publications

References 27 publications

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

Application of Selective Crystallization Methods To Isolate the Metastable Polymorphs of Paracetamol: A Review

Quantitative analysis of calcium oxalate monohydrate and dihydrate for elucidating the formation mechanism of calcium oxalate kidney stones

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