Effect of Cryogrinding on Chemical Stability of the Sparingly Water-Soluble Drug Furosemide

Adrjanowicz, Karolina; Kamiński, Kamil; Grzybowska, K.; Hawełek, ᴌ.; Paluch, Marian; Gruszka, Irena; Żakowiecki, Daniel; Sawicki, Wiesław; Lepek, P.; Kamysz, Wojciech; Guzik, Łukasz

doi:10.1007/s11095-011-0496-4

Cited by 44 publications

(65 citation statements)

References 35 publications

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“…Milling can also impact the chemical stability. Cryomilling has been shown to amorphize furesomide [47] and also to induce some chemical degradation and appearance of impurities. Such chemical degradation can be linked to the modification of the structural relaxations and specificity of the sub-Tg molecular mobility revealed by our investigation.…”

Section: Conclusion Link With Physical and Chemical Stabilitymentioning

confidence: 99%

The amorphous state of pharmaceuticals obtained or transformed by milling: Sub-Tg features and rejuvenation

Descamps

Aumelas²,

Desprez

et al. 2015

Journal of Non-Crystalline Solids

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Section: Conclusion Link With Physical and Chemical Stabilitymentioning

confidence: 99%

The amorphous state of pharmaceuticals obtained or transformed by milling: Sub-Tg features and rejuvenation

Descamps

Aumelas²,

Desprez

et al. 2015

Journal of Non-Crystalline Solids

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“…Milling is one the most common particle size reduction step. The effect of milling parameters, such as milling frequency, impact velocity, milling time on particle bulk and surface properties, is well documented in the literature Adrjanowicz et al, 2011;Forcino et al, 2010;Vegt et al, 2009;Shariare et al, 2011;Perkins et al, 2009;Kwan et al, 2004;Kwan et al, 2003;Leleux and Williams, 2014;Newman and Zografi, 2014). Kwan et al investigated the effect of milling frequency and propensity of breakage for microcrystalline cellulose and α-lactose monohydrate.…”

Section: Introductionmentioning

confidence: 99%

“…Adrjanowicz et al demonstrated that milling at cryogenic temperature can result in chemical decomposition of furosemide. Chemical stability of furosemide was reported to be effected by the generation of the amorphous phase under cryogenic milling conditions (Adrjanowicz et al, 2011). A higher reactivity of the amorphous phase was linked to the acid catalysed hydrolysis of the amorphous phase of furosemide, resulting in undesirable chemical changes.…”

Section: Introductionmentioning

confidence: 99%

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Effect of milling temperatures on surface area, surface energy and cohesion of pharmaceutical powders

Shah

Wang

Olusanmi

et al. 2015

International Journal of Pharmaceutics

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Particle bulk and surface properties are influenced by the powder processing routes. This study demonstrates the effect of milling temperatures on the particle surface properties, particularly surface energy and surface area, and ultimately on powder cohesion. An active pharmaceutical ingredient (API) of industrial relevance (brivanib alaninate, BA) was used to demonstrate the effect of two different, but most commonly used milling temperatures (cryogenic vs. ambient). The surface energy of powders milled at both cryogenic and room temperatures increased with increasing milling cycles. The increase in surface energy could be related to the generation of surface amorphous regions. Cohesion for both cryogenic and room temperature milled powders was measured and found to increase with increasing milling cycles. For cryogenic milling, BA had a surface area ∼ 5× higher than the one obtained at room temperature. This was due to the brittle nature of this compound at cryogenic temperature. By decoupling average contributions of surface area and surface energy on cohesion by salinization post-milling, the average contribution of surface energy on cohesion for powders milled at room temperature was 83% and 55% at cryogenic temperature.

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“…In addition, the solubility of API is expected to be improved via amorphization. However, physical and chemical stabilities remain still challenging in cryogenic co-grinding 13 , and consequently, the inclusion of a stabilizing carrier polymer or polymer mixture is essential.…”

Section: Introductionmentioning

confidence: 99%

Towards improved solubility of poorly water-soluble drugs: cryogenic co-grinding of piroxicam with carrier polymers

Penkina

Semjonov

Hakola

et al. 2015

Drug Development and Industrial Pharmacy

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Amorphous solid dispersions (SDs) open up exciting opportunities in formulating poorly watersoluble active pharmaceutical ingredients (APIs). In the present study, novel catalytic pretreated softwood cellulose (CPSC) and polyvinylpyrrolidone (PVP) were investigated as carrier polymers for preparing and stabilizing cryogenic co-ground SDs of poorly water-soluble piroxicam (PRX). CPSC was isolated from pine wood (Pinus sylvestris). Raman and Fourier transform infrared (FTIR) spectroscopy, X-ray powder diffraction (XRPD) and differential scanning calorimetry (DSC) were used for characterizing the solid-state changes and drug-polymer interactions. Highresolution scanning electron microscope (SEM) was used to analyze the particle size and surface morphology of starting materials and final cryogenic co-ground SDs. In addition, the molecular aspects of drug-polymer interactions and stabilization mechanisms are presented. The results showed that the carrier polymer influenced both the degree of amorphization of PRX and stabilization against crystallization. The cryogenic co-ground SDs prepared from PVP showed an enhanced dissolution rate of PRX, while the corresponding SDs prepared from CPSC exhibited a clear sustained release behavior. In conclusion, cryogenic co-grinding provides a versatile method for preparing amorphous SDs of poorly water-soluble APIs. The solid-state stability and dissolution behavior of such co-ground SDs are to a great extent dependent on the carrier polymer used.

show abstract

Effect of Cryogrinding on Chemical Stability of the Sparingly Water-Soluble Drug Furosemide

Cited by 44 publications

References 35 publications

The amorphous state of pharmaceuticals obtained or transformed by milling: Sub-Tg features and rejuvenation

The amorphous state of pharmaceuticals obtained or transformed by milling: Sub-Tg features and rejuvenation

Effect of milling temperatures on surface area, surface energy and cohesion of pharmaceutical powders

Towards improved solubility of poorly water-soluble drugs: cryogenic co-grinding of piroxicam with carrier polymers

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