Change in glycine polymorphs induced by minute-bubble injection during antisolvent crystallisation

Matsumoto, Masakazu; Wada, Yasuhiro; Onoe, Kaoru

doi:10.1016/j.apt.2014.11.014

Cited by 13 publications

(8 citation statements)

References 33 publications

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“…It was observed that impinging jet crystallization combined with cooling is a very effective and reproducible method for reducing the particle size of cilostazol. This method resulted in significantly smaller particle size (d(0.5) = 3-5 µm) and more uniform crystals compared to the original ground material (d(0.5) = 24 µm) or the conventional methods (d(0.5) = 8-14 µm), and it also resulted in a stable polymorphic form and enhanced the dissolution rate.Crystals 2019, 9, 295 2 of 15 temperature, cooling rate, solvent-antisolvent ratio and quality, active pharmaceutical ingredient (API) concentration, mixing factors, etc., can influence the physicochemical properties of the product [12][13][14]. However, the conventional route can reduce particle size only within certain limits.…”

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Comparative Study of Different Crystallization Methods in the Case of Cilostazol Crystal Habit Optimization

2019

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The therapeutic usage of cilostazol is limited owing to its poor aqueous solubility and oral bioavailability. Our aim was to produce cilostazol crystals with small average particle size; besides suitable roundness, narrow particle size distribution and stable polymorphic form to increase its dissolution rate and improve processability. Different conventional crystallization methods with or without sonication were compared with impinging jet crystallization combined with cooling, and the optimization of the various parameters was also implemented. The effects of post-mixing time and temperature difference were studied by means of a full factorial design. The physical properties of powder particles were characterized by, i.a., XRPD, DSC and SEM. The dissolution rate and the contact angle of solid surfaces were also determined to elucidate the relationship between wettability and dissolution. It was observed that impinging jet crystallization combined with cooling is a very effective and reproducible method for reducing the particle size of cilostazol. This method resulted in significantly smaller particle size (d(0.5) = 3-5 µm) and more uniform crystals compared to the original ground material (d(0.5) = 24 µm) or the conventional methods (d(0.5) = 8-14 µm), and it also resulted in a stable polymorphic form and enhanced the dissolution rate.Crystals 2019, 9, 295 2 of 15 temperature, cooling rate, solvent-antisolvent ratio and quality, active pharmaceutical ingredient (API) concentration, mixing factors, etc., can influence the physicochemical properties of the product [12][13][14]. However, the conventional route can reduce particle size only within certain limits. Therefore, several alternative processes have been developed for the control and modification of the solid-state properties of APIs. For example, laminar-flow tubular crystallizer was used to produce selectively the desired polymorphic form of brivaracetam [15], multi-inlet vortex mixer was redesigned to facilitate formulation screening in small-scale experiments with biologics [16], or continuous plug flow crystallization was applied to generate particles with controlled characteristics [17]. Based on the literature, ultrasound application in crystallization is suitable for modifying the quality of the crystals. It can reduce the metastable zone width, and generate rapid, uniform mixing, which reduces the agglomeration of particles [18,19]. Higher sonication intensity and longer sonication time favour the formation of smaller crystals with narrow PSD [20][21][22].Impinging jet crystallization is a relatively new field for the researchers in pharmaceutical manufacturing and industrial crystallization [23]. However, it is proved that this method effectively reduces particle size, as well as it has the potential advantage to produce reproducible products with small average particle size and narrow PSD [24]. The rich solution of the API and the antisolvent flow through two jet nozzles, which are arranged diametrically opposite each other, and it enables the ...

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confidence: 99%

“…Crystals 2019, 9, 295 2 of 15 temperature, cooling rate, solvent-antisolvent ratio and quality, active pharmaceutical ingredient (API) concentration, mixing factors, etc., can influence the physicochemical properties of the product [12][13][14]. However, the conventional route can reduce particle size only within certain limits.…”

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confidence: 99%

Comparative Study of Different Crystallization Methods in the Case of Cilostazol Crystal Habit Optimization

2019

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“…Therefore, ultrasonic irradiation generates the bubbles which remain in water and ethanol at least for several minutes. It has been reported that a minute nitrogen bubble increass the local supersaturation at its interface . The bubble generated by ultrasonic irradiation seems to be one of the mechanisms of the polymorph control.…”

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confidence: 99%

Polymorph Control of L‐ArgHCl on Antisolvent Crystallization by Ultrasonic Irradiation

Ike

Hirasawa

2017

Chem Eng & Technol

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Amino acids are utilized as medical raw materials and food additives. It is wellknown that most of the amino acids show polymorphism. Differences in the crystal structures affect the physical and chemical properties. Therefore, an effective method for polymorph control is required in the crystallization process. Polymorph control of L-arginine hydrochloride (L-ArgHCl) on antisolvent crystallization was achieved by ultrasonic irradiation. L-ArgHCl exhibits polymorphism and crystallizes into three distinct crystal forms. Without irradiation, the metastable form was selectively crystallized. In contrast, the unstable form was selectively crystallized by irradiation. Irradiation after the addition of an antisolvent led to a shorter induction time.

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“…These differences influence the process acceptability, bioavailability, filtration, and tabletting processes of pharmaceutical, food, and specialty materials. Therefore, an effective method for polymorph and pseudo-polymorph control is required in the crystallization process to improve the functionality of crystals and process efficiency [1][2][3][4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Polymorph Control of L‐Phenylalanine in Cooling Crystallization by Ultrasonication

Ike

Hirasawa

2018

Chem Eng & Technol

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Most of the amino acids that are utilized as medical raw materials and food additives show polymorphism. To improve the physical and chemical properties of the crystals, an effective method for polymorph control is required in the crystallization process. In this study, polymorph control of L‐phenylalanine in cooling crystallization by ultrasonication was investigated. L‐Phenylalanine crystallizes in anhydrate and monohydrate forms. Without ultrasonication, a mixture of monohydrate and anhydrate forms was obtained. In contrast, the yield of monohydrate was increased by ultrasonication. In addition, ultrasonication shortened the induction time. It was considered that ultrasonic energy could supply the energy required for primary nucleation.

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Change in glycine polymorphs induced by minute-bubble injection during antisolvent crystallisation

Cited by 13 publications

References 33 publications

Comparative Study of Different Crystallization Methods in the Case of Cilostazol Crystal Habit Optimization

Comparative Study of Different Crystallization Methods in the Case of Cilostazol Crystal Habit Optimization

Polymorph Control of L‐ArgHCl on Antisolvent Crystallization by Ultrasonic Irradiation

Polymorph Control of L‐Phenylalanine in Cooling Crystallization by Ultrasonication

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