β-cyclodextrin complexation as an approach to enhance the biopharmaceutical properties of Norfloxacin B Hydrate

Bueno, Maria Soledad; Chierentin, Lucas; Bongioanni, Agustina; Salgado, Hérida Regina Nunes; Longhi, Marcela Raquel; Garnero, Claudia

doi:10.1016/j.carres.2019.107818

Cited by 11 publications

(7 citation statements)

References 17 publications

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“…The dissolution rate of the PMs was slightly higher than that of crystalline RBG, and the cumulative dissolution rate reached 50% and 53% at 240 min for RBG/β-CD and RBG/HP-β-CD, respectively. This could be attributed to the improved drug wettability of PMs due to the presence of hydrophilic cyclodextrin, which can reduce the interfacial tension between poorly water-soluble drugs and dissolution medium [ 46 , 47 ]. However, the inclusion complexes exhibited much faster dissolution rates, as evidenced by the fact that approximately 99% of the RBG from inclusion complexes were dissolved within 5 min, while only about 50% and 30% of RBG were dissolved from PMs and crystalline RBG within 4 h, respectively.…”

Section: Resultsmentioning

confidence: 99%

Enhancement of Dissolving Capacity and Reducing Gastric Mucosa Irritation by Complex Formation of Resibufogenin with β-Cyclodextrin or 2-Hydroxypropyl-β-cyclodextrin

et al. 2022

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Resibufogenin (RBG) is a natural medicinal ingredient with promising cardiac protection and antitumor activity. However, poor solubility and severe gastric mucosa irritation restrict its application in the pharmaceutical field. In this study, the inclusion complex of RBG with β-cyclodextrin (β-CD) and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) was prepared using the co-evaporation method, and the molar ratio of RBG to CD was determined to be approximately 1:2 by continuous variation plot for both CDs. The formation of inclusion complexes between RBG and each CD (RBG/β-CD and RBG/HP-β-CD) was evaluated by phase solubility study, Fourier transform infrared spectroscopy, and thin-layer chromatography. Powder X-ray diffraction and differential scanning calorimetry confirmed drug amorphization and encapsulation in the molecular cage for both CDs. Moreover, the inclusion complexes’ morphologies were observed using scanning electron microscopy. The dissolution rate of the inclusion complexes was markedly improved compared to that of RBG, and the complexes retained their antitumor activity, as shown in the in vitro cytotoxicity assay on a human lung adenocarcinoma cancer (A549) cell line. Moreover, less gastric mucosal irritation was observed for the inclusion complex. Thus, the inclusion complex should be considered a promising strategy for the delivery of poorly water-soluble anticancer agents, such as RBG.

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Section: Resultsmentioning

confidence: 99%

Enhancement of Dissolving Capacity and Reducing Gastric Mucosa Irritation by Complex Formation of Resibufogenin with β-Cyclodextrin or 2-Hydroxypropyl-β-cyclodextrin

et al. 2022

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“…In general, different polymorphs show solubility differences typically smaller than 10 times due to relative differences in free energy. Some examples include the evaluation of solubility, in aqueous and buffer solutions, of several forms of furosemide [47], norfloxacin [48][49][50], albendazole [51], and oxytetracycline hydrochloride [52]. These studies demonstrate that the molecular arrangement of each polymorphic form and its degree of ionization has a considerable impact on drug solubility (Table 1).…”

Section: Solid Form Impact On Physicochemical and Biopharmaceutical P...mentioning

confidence: 99%

Pharmaceutical Crystals: Development, Optimization, Characterization and Biopharmaceutical Aspects

Bongioanni¹,

Bueno²,

Mezzano³

et al. 2023

Crystal Growth and Chirality - Technologies and Applications

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In the solid state, the active pharmaceutical ingredients tend to exhibit crystalline order. In this regard, the interest in the crystalline solid state has expanded to include single-component compounds as well as multicomponent systems such as salts, hydrates, solvates, and co-crystals. The study of crystalline behavior is recognized as an essential component of preformulation research in pharmaceutical sciences and industries. The crystalline form can impact the drug properties such as solubility, dissolution rate, stability, hygroscopicity, and toxicity profile. Therefore, each solid form must be appropriately identified and characterized because it will affect the drug formulation, including the pharmacokinetic, pharmacodynamic, and safety properties of the formulation. In this context, this chapter will cover topics such as synthesis approaches (including nucleation and crystallization procedures), crystal polymorphism, solid state characterization techniques and the impact of crystals on physicochemical and biopharmaceutical properties.

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“…Several articles describe the complexes of individual polymorphs of norfloxacin with β-CD, obtained by the kneading and freeze-drying methods [ 171 , 172 , 173 , 174 ]. Norfloxacin exists in several solid forms: three anhydrous polymorphs (Forms A, B, and C), an amorphous form, a methanol solvate, and several hydrate forms, as well as salts and co-crystals [ 171 ].…”

Section: Quinolonesmentioning

confidence: 99%

“…Norfloxacin exists in several solid forms: three anhydrous polymorphs (Forms A, B, and C), an amorphous form, a methanol solvate, and several hydrate forms, as well as salts and co-crystals [ 171 ]. Norfloxacin A [ 172 ], B I (B hydrate) [ 173 ], and C [ 174 ] were tested separately for complexation with β-CD and their antimicrobial activity, revealing that all forms exhibited microbiological activity, among which the B I form had the most potent activity. This polymorph was found to be the best candidate for the preparation of alternative matrices using β-CD to enhance the biopharmaceutical properties.…”

Section: Quinolonesmentioning

confidence: 99%

Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

Boczar

Michalska

2022

Pharmaceutics

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Cyclodextrins (CDs) are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits linked by α-1,4 glycosidic bonds. The shape of CD molecules is similar to a truncated cone with a hydrophobic inner cavity and a hydrophilic surface, which allows the formation of inclusion complexes with various molecules. This review article summarises over 200 reports published by the end of 2021 that discuss the complexation of CDs with antibiotics and antibacterial agents, including beta-lactams, tetracyclines, quinolones, macrolides, aminoglycosides, glycopeptides, polypeptides, nitroimidazoles, and oxazolidinones. The review focuses on drug-delivery applications such as improving solubility, modifying the drug-release profile, slowing down the degradation of the drug, improving biological membrane permeability, and enhancing antimicrobial activity. In addition to simple drug/CD combinations, ternary systems with additional auxiliary substances have been described, as well as more sophisticated drug-delivery systems including nanosponges, nanofibres, nanoparticles, microparticles, liposomes, hydrogels, and macromolecules. Depending on the desired properties of the drug product, an accelerated or prolonged dissolution profile can be achieved when combining CD with antibiotics or antimicrobial agents.

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β-cyclodextrin complexation as an approach to enhance the biopharmaceutical properties of Norfloxacin B Hydrate

Cited by 11 publications

References 17 publications

Enhancement of Dissolving Capacity and Reducing Gastric Mucosa Irritation by Complex Formation of Resibufogenin with β-Cyclodextrin or 2-Hydroxypropyl-β-cyclodextrin

Enhancement of Dissolving Capacity and Reducing Gastric Mucosa Irritation by Complex Formation of Resibufogenin with β-Cyclodextrin or 2-Hydroxypropyl-β-cyclodextrin

Pharmaceutical Crystals: Development, Optimization, Characterization and Biopharmaceutical Aspects

Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

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