The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Ilić‐Stojanović, Snežana; Nikolić, Vesna; Nikolić, Ljubiša; Zdravković, Aleksandar; Kapor, Á.; Popsavin, Mirjana; Petrović, Slobodan

doi:10.2298/hemind131128050i

Cited by 14 publications

(18 citation statements)

References 24 publications

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“…Finally, TBPs 1, 2, 13 and 14 are detected only in samples after 240 min of treatment and at low concentration levels and thus they can be considered as later stage products. For the sake of comparison with other studies dealing with the degradation of PRX, TBP 14 and structurally similar TBPs have been identified as degradation products of PRX under oxidative and photolytic conditions . In addition, the in vivo formation of the metabolic oxidation product 5‐hydroxypiroxicam and at least 13 new secondary peaks (without structure identification) after the in vitro study of hydroxyl radical attack of PRX was reported elsewhere …”

Section: Resultsmentioning

confidence: 94%

“…Ring cleavage of this unstable intermediate, leads to its conversion in a carboxylic acid structure, as depicted in Fig. which is further transformed to later stages TBPs, such as TBP 1, 2, 13 and 14. The same degradation mechanism was proposed for the photochemical oxidation of PRX …”

Section: Resultsmentioning

confidence: 99%

“…For the sake of comparison with other studies dealing with the degradation of PRX, TBP 14 and structurally similar TBPs have been identified as degradation products of PRX under oxidative and photolytic conditions. [29][30][31][32] In addition, the in vivo formation of the metabolic oxidation product 5-hydroxypiroxicam and at least 13 new secondary peaks (without structure identification) after the in vitro study of hydroxyl radical attack of PRX was reported elsewhere. 33 Taking into account the identification and structural assignment of the TBPs, as well as their evolution profiles, the sonochemical degradation mechanisms of PRX are proposed in Fig.…”

Section: Identification Of Transformation By-products (Tbps) and Degrmentioning

confidence: 99%

mentioning

confidence: 99%

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Sonochemical oxidation of piroxicam drug: effect of key operating parameters and degradation pathways

Lianou

Frontistis

Chatzisymeon

et al. 2017

J of Chemical Tech & Biotech

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BACKGROUND Piroxicam (PRX) is a non‐steroidal anti‐inflammatory drug (NSAID) commonly used to relieve pain and swelling of conditions like arthritis. PRX has been extensively detected in seawater, surface, and sewage waters worldwide and therefore its efficient treatment is an issue of emerging concern. In this work, the sonochemical degradation of PRX was investigated. RESULTS All experiments were conducted at constant ultrasound frequency of 20 kHz while the following range of experimental conditions was investigated: initial PRX concentration 320–960 µg L‐1, ultrasound power density 20–60 W L‐1, temperature 20–60 °C, reaction time up to 60 min. The effect of different water matrices, namely surface water (SW), bottled water (BW), ultrapure water (UPW) and humic acid (HA) aqueous solution on process efficiency was also explored. It was found that PRX degradation reached 96% after only 10 min of treatment under the best conditions (i.e. [PRX]0 = 320 mg L‐1, 20 °C, 36 W L‐1) assayed. Power density could positively affect PRX degradation. Nevertheless, PRX degradation decreased when its initial concentration and the temperature of the bulk liquid was increased. PRX degradation was found to decrease, in different water matrices, in the order: UPW > 5 mg L‐1 HA > BW > 10 mg L‐1 HA > SW. High resolution mass spectrometry analysis revealed that 14 transformation by‐products (TBPs) were formed and subsequently degraded during treatment while the PRX degradation pathways were also elucidated. CONCLUSION At the optimal operating conditions assayed, PRX was efficiently degraded after about 10 min of sonochemical oxidation, thus rendering it a promising technology for the treatment of xenobiotics. © 2017 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Identification Of Transformation By-products (Tbps) and Degrmentioning

confidence: 99%

mentioning

confidence: 99%

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Sonochemical oxidation of piroxicam drug: effect of key operating parameters and degradation pathways

Lianou

Frontistis

Chatzisymeon

et al. 2017

J of Chemical Tech & Biotech

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“…Tworzenie kompleksów inkluzyjnych z cyklodekstrynami jest coraz częściej badane i chętniej wykorzystywane. Dzięki oddziaływaniom z API połączenie takie zwiększa rozpuszczalność substancji (ibuprofen [23]), zwiększa jej stabilność (modafinil [24]), fotostabilność (naproksen [25]) i biodostępność (indometacyna [26]), redukuje działanie drażniące (itrakonazol [27]) i liczbę działań niepożądanych, maskuje nieprzyjemny zapach i smak (famotydyna [28]). Z drugiej jednak strony może się zdarzyć, że zainkludowanie substancji leczniczej do wnętrza cyklodekstryny będzie miało zarówno pozytywne, jak i negatywne efekty.…”

Section: Rycina 2 Budowa β-Cyklodekstrynyunclassified

Sacharides and their derivatives as pharmaceutical additives

Milewska¹,

Klucznik²,

Jamrógiewicz³

2018

Farm Pol.

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Efficient Synthesis of Submicrometer‐Sized Active Pharmaceuticals by Laser Fragmentation in a Liquid‐Jet Passage Reactor with Minimum Degradation

Friedenauer,

Buck,

Eberwein

et al. 2023

Part & Part Syst Charact

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One challenge in the development of new drug formulations is overcoming their low solubility in relevant aqueous media. Reducing the particle size of drug powders to a few hundred nanometers is a well‐known method that leads to an increase in solubility due to an elevated total surface area. However, state‐of‐the‐art comminution techniques like cryo‐milling suffer from degradation and contamination of the drugs, particularly when sub‐micrometer diameters are aspired that require long processing times. In this work, picosecond‐pulsed laser fragmentation in liquids (LFL) of dispersed drug particles in a liquid‐jet passage reactor is used as a wear‐free comminution technique using the hydrophobic oral model drugs naproxen, prednisolone, ketoconazole, and megestrol acetate. Particle size and morphology of the drug particles are characterized using scanning electron microscopy (SEM) and changes in particle size distributions upon irradiation are quantified using an analytical centrifuge. The findings highlight the superior fragmentation efficiency of the liquid‐jet passage reactor setup, with a 100 times higher fraction of submicrometer particles (SMP) of the drugs compared to the batch control, which enhances solubility and goes along with minimal chemical degradation (<1%), determined by attenuated total reflection‐Fourier transform infrared spectroscopy (ATR‐FTIR), high‐performance liquid chromatography (HPLC), and X‐ray diffraction (XRD). Moreover, the underlying predominantly photo‐mechanically induced laser fragmentation mechanisms of organic microparticles (MP) are discussed.

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The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Cited by 14 publications

References 24 publications

Sonochemical oxidation of piroxicam drug: effect of key operating parameters and degradation pathways

Sonochemical oxidation of piroxicam drug: effect of key operating parameters and degradation pathways

Sacharides and their derivatives as pharmaceutical additives

Efficient Synthesis of Submicrometer‐Sized Active Pharmaceuticals by Laser Fragmentation in a Liquid‐Jet Passage Reactor with Minimum Degradation

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