Zaleplon co-ground complexes with natural and polymeric β-cyclodextrin

Jablan, Jasna; Bačić, Ivana; Kujundžić, Nikola; Jug, Mario

doi:10.1007/s10847-012-0206-9

Cited by 6 publications

(4 citation statements)

References 29 publications

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“…While the co-ground products of zaleplon with β-CD and polymeric β-CD derivative contained 51.10 and 12.05% of residual drug crystallinity (RDC), they showed significant improvement of the drug dissolution rate of 58.5 and 98.0% with respect to that of pure drug. This was attributed to the actual inclusion complexes formation upon dissolution, confirmed by 1 H-NMR spectroscopy [77]. Grinding has often proved to be more effective than other techniques, such as kneading or coevaporation, in inducing complete amorphization of different drugs in combination with different CDs, such as clonazepam with βCD, HPβCD, and RAMEB [32], or oxaprozin in systems with both natural and derivative CDs [34], or naproxen with acetylated βCD and γCD [64].…”

Section: Mechanism Of the Inclusion Complex Formation In The Solidmentioning

confidence: 92%

“…Several authors have demonstrated, by the use of 13 C MAS CP/TOSS NMR spectroscopy, the actual inclusion complex formation in amorphous drug/CD products obtained by co-grinding; examples from the literature included two thiadiazole-based anti-Alzheimer drug candidates co-ground with βCD and HPβCD [27,37], a fentanyl/βCD [59], and a bisacodyl/βCD [54] co-ground system. However, even if the product contains a significant fraction of residual crystalline drug, it could be readily converted into inclusion complex upon dissolution in water, as demonstrated by Jablan et al [77]. While the co-ground products of zaleplon with β-CD and polymeric β-CD derivative contained 51.10 and 12.05% of residual drug crystallinity (RDC), they showed significant improvement of the drug dissolution rate of 58.5 and 98.0% with respect to that of pure drug.…”

Section: Mechanism Of the Inclusion Complex Formation In The Solidmentioning

confidence: 99%

“…In general, co-grinding with crystalline CD derivatives leads to only partial drug complexation (i.e., formation of partially crystalline products) [32,77] or requires longer grinding time until complete product amorphization [31], which is generally accepted as an indication of inclusion complex formation in the solid state. On the other hand, hydrophilic βCD derivatives are more effective than natural βCD in establishing solid-state interactions with the drug by grinding.…”

Section: Process Variables Of the Inclusion Complex Formation In Tmentioning

confidence: 99%

“…From the examples reported in Table 2, it appears evident that, among the different CD derivatives, polymeric CDs also proved to be very effective as co-grinding additives, producing amorphous complexes with enhanced dissolution properties [47,74,77,79,81]. Furthermore, co-grinding with βCD-EPI enhanced antibacterial activity of triclosan against Streptococcus mutans , that has a major role in etiology of caries [79].…”

Section: Process Variables Of the Inclusion Complex Formation In Tmentioning

confidence: 99%

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Grinding as Solvent-Free Green Chemistry Approach for Cyclodextrin Inclusion Complex Preparation in the Solid State

Jug

Mura

2018

Pharmaceutics

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Among the different techniques proposed for preparing cyclodextrin inclusion complex in the solid state, mechanochemical activation by grinding appears as a fast, highly efficient, convenient, versatile, sustainable, and eco-friendly solvent-free method. This review is intended to give a systematic overview of the currently available data in this field, highlighting both the advantages as well as the shortcomings of such an approach. The possible mechanisms involved in the inclusion complex formation in the solid state, by grinding, have been illustrated. For each type of applied milling device, the respective process variables have been examined and discussed, together with the characteristics of the obtained products, also in relation with the physicochemical characteristics of both the drug and cyclodextrin subjected to grinding. The critical process parameters were evidenced in order to provide a useful guide for a rational selection of the most suitable conditions for an efficient inclusion complex preparation by grinding, with the final purpose of promoting a wider use of this effective solvent-free cyclodextrin inclusion complex preparation method in the solid state.

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Section: Mechanism Of the Inclusion Complex Formation In The Solidmentioning

confidence: 92%

Section: Mechanism Of the Inclusion Complex Formation In The Solidmentioning

confidence: 99%

Section: Process Variables Of the Inclusion Complex Formation In Tmentioning

confidence: 99%

Section: Process Variables Of the Inclusion Complex Formation In Tmentioning

confidence: 99%

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Grinding as Solvent-Free Green Chemistry Approach for Cyclodextrin Inclusion Complex Preparation in the Solid State

Jug

Mura

2018

Pharmaceutics

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Cyclodextrin‐Based Molecular Inclusion by Grinding

Sharma,

Naman,

Baldi

2023

Sustainable Approaches in Pharmaceutical Sciences

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Comparative analysis of binary and ternary cyclodextrin complexes with econazole nitrate in solution and in solid state

Jug

Mennini

Kövér

et al. 2014

Journal of Pharmaceutical and Biomedical Analysis

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The aim of this work was to investigate in-depth interactions of econazole nitrate (ECN), a very poorly water-soluble antifungal agent, with different β-cyclodextrin (βCD) derivatives, and to evaluate the potential synergistic effect of suitable third compounds (l-amino acids, citric acid, hydrophilic polymers). Phase-solubility studies showed the formation of equimolar complexes with all tested CDs, and indicated sulfobutyl-βCD (SBEβCD) as the best complexing and solubilizing agent for ECN, followed by hydroxypropyl-βCD (HPβCD). 1D and 2D (1)H NMR studies demonstrated the actual formation of inclusion complexes of 1:1mol:mol stoichiometry, and gave insight about different inclusion modes of ECN molecule into the CD cavity, simultaneously existing in solution. Among the different tested ternary systems, only those with citric acid (CA) enabled a significant increase in complexing and solubilizing ability towards the drug with respect to the binary ones, indicating a synergistic effect between SBEβCD and CA and the formation of highly soluble ternary complexes, which was further supported by NMR studies. Solid equimolar binary and ternary systems of ECN, CDs and CA were prepared by co-grinding in high energy vibrational micro-mills and characterized by differential scanning calorimetry, X-ray powder diffractometry and in vitro dissolution studies. In the case of binary systems, total sample amorphization, indicative of strong solid state interactions and possible inclusion complex formation, was obtained only for co-ground products with HPβCD and SBEβCD, but they both presented a dissolution profile typical of a supersaturated system, with a limited improvement of drug dissolution efficiency (8.3 and 22.13 times, respectively). On the contrary, the ternary ECN/SBEβCD/CA co-ground product presented superior dissolution properties, increasing the ECN dissolution efficiency of 66.62 times, clearly having the best potential for further development of a novel ECN delivery system for efficient delivery of the drug to the oral cavity, thus improving the therapy of oral candidosis.

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Zaleplon co-ground complexes with natural and polymeric β-cyclodextrin

Cited by 6 publications

References 29 publications

Grinding as Solvent-Free Green Chemistry Approach for Cyclodextrin Inclusion Complex Preparation in the Solid State

Grinding as Solvent-Free Green Chemistry Approach for Cyclodextrin Inclusion Complex Preparation in the Solid State

Cyclodextrin‐Based Molecular Inclusion by Grinding

Comparative analysis of binary and ternary cyclodextrin complexes with econazole nitrate in solution and in solid state

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