Characterization of systems with amino-acids and oligosaccharides as modifiers of biopharmaceutical properties of furosemide

Abraham-Miranda, Julieta; Garnero, Claudia; Zoppi, Ariana; Sterren, Vanesa B.; Ayala, A. P.; Longhi, Marcela R.

doi:10.1016/j.jpba.2017.10.038

Cited by 14 publications

(11 citation statements)

References 32 publications

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“…The FTIR spectrum of furosemide (Figure 4), in agreement with previous studies [26], included two characteristic absorption bands at 3397 and 3282 cm −1 ascribed to sulfonamide NH stretching, a secondary amine NH stretching vibration at 3351 cm −1 , NH bending at 1562–1591 cm −1 , and characteristic C=O and S=O bands at 1671 and 1141 cm −1 , respectively. In the FTIR spectra of the L100, S100, L100-55, and E100 polymers, similar characteristic absorption bands were observed.…”

Section: Resultssupporting

confidence: 88%

“…In the DSC analysis (Figure 3a), furosemide, in agreement with the literature [26], showed a weak endotherm at 136.8 °C, a melting endotherm at 219.2 °C, followed by a sharp exothermic peak at 223.7 °C and two endotherms at 270 and 277.5 °C, which were associated with the decomposition phenomena of the drug. The raw Eudragit ® polymers, due to their amorphous state, showed broad dehydration endothermic bands below 100 °C, which were followed by broad endotherms over 200 °C due to the decomposition of the polymers.…”

Section: Resultssupporting

confidence: 88%

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Development and Characterization of Eudragit®-Based Electrospun Nanofibrous Mats and Their Formulation into Nanofiber Tablets for the Modified Release of Furosemide

et al. 2019

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Furosemide, a chloride channel blocker ordinarily used as a high-ceiling or loop diuretic, is practically insoluble in water and dilute acids. Due to its acidic nature, furosemide is mostly absorbed in the stomach and in the upper small intestine. Efforts have focused on the development of sustained release systems of furosemide in order to improve the effectiveness of the drug, which exhibits poor aqueous solubility and poor permeability. Recently, electrospun nanofibrous drug delivery systems have emerged as promising alternative solid-dosage forms due to their advantages of high porosity, high surface to volume ratio, and high drug-loading efficacy. Herein, a number of nanofibrous mats composed of different types of Eudragit® polymers in various concentrations and combinations loaded with furosemide were designed, successfully electrospun, and characterized using SEM, FTIR, DSC, and TGA analyses. The nanofibrous nonwovens were formulated in nanofiber tablets and the release profile of furosemide from them was evaluated at pH 1.2 and 6.8 and compared to that of physical mixture matrix tablets of analogous composition as well as to that of a commercial formulation. It was found that the release of furosemide was compatible with the gastroretentive and slower intestinal release requirements with a well-defined absorption window, while some nanofiber formulations could act as furosemide carriers in emergency situations where a relatively fast onset of its action is required, as in the case of critically ill post-traumatic patients.

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Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 88%

Development and Characterization of Eudragit®-Based Electrospun Nanofibrous Mats and Their Formulation into Nanofiber Tablets for the Modified Release of Furosemide

et al. 2019

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“…Water, tetrahydrofuran, and acetic acid (70:30:1, v/v/v) were used as a mobile phase. The flow rate was kept at 1.5 mL/min, and the detection wavelength was performed at 274 nm . To ensure the accuracy of the experimental data, all dissolution data were repeated 3 times, and the average value was regarded as the final result (standard curve can be seen in Figure S2).…”

Section: Materials and Methodsmentioning

confidence: 99%

Co-amorphization Story of Furosemide-Amino Acid Systems: Protonation and Aromatic Stacking Insights for Promoting Compatibility and Stability

Wang

Liu

et al. 2021

Crystal Growth & Design

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Furosemide (FUR) is usually used to treat congestive heart failure and edema. Although bioavailability problems exist due to its poor solubility and unstable gastrointestinal absorption, preparing FUR/amino acid (AA) co-amorphous systems is regarded as a promising way to solve this problem. In this work, the oscillating ball milling method was successfully used to prepare the co-amorphous systems of FUR with l-cysteine, l-phenylalanine (PHE), l-arginine, l-tryptophan (TRP), and l-valine. Protonation of the secondary amino group (N2) in FUR probably results in interactions with the AA carboxyl group, which lead to excellent compatibility between FUR and AAs. The co-amorphous systems formed between FUR and PHE/TRP possess higher physical stability than other FUR/AA co-amorphous systems, which may be attributed to favorable aromatic stacking in FUR/PHE and FUR/TRP systems. Additional experiments were performed to explore the impact of co-former loadings on the stability of co-amorphous systems, which revealed that the co-amorphous systems are most stable when the molar ratios are at 0.527 and 0.423 for FUR in FUR/PHE and FUR/TRP systems, respectively. Finally, powder dissolution tests of the FUR/PHE and FUR/TRP co-amorphous systems were carried out, and the results demonstrated that the selected most stable co-amorphous systems have excellent dissolution advantage with a two-fold improvement of dissolution rate compared to pure FUR.

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“…Nonetheless, GBC-ARG and GBC-ARG-SLS did display significant differences in terms of GBC solubility as compared to crystalline GBC. The increase in the solubility of GBC-ARG may be explained by the presence of ARG which has been reported to form salts with different molecules (Lenz et al, 2015) and act as a solubility enhancer of poorly water soluble drugs through intermolecular interactions (Hirano et al, 2010;Miranda et al, 2018). In their study, Miranda et al (2018) noted that there was a linear ARG concentration dependent increase in the solubility of a poorly water soluble drug furosemide.…”

Section: The Equilibrium Solubility Of Gbc In Hbssmentioning

confidence: 96%

The effect of co-amorphization of glibenclamide on its dissolution properties and permeability through an MDCKII-MDR1 cell layer

Sormunen

Ruponen

Laitinen

2019

International Journal of Pharmaceutics

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Co-amorphous mixtures have been demonstrated to represent a promising approach for enhancing the dissolution of poorly water-soluble drugs. However, little is known of their permeability properties, especially through biological membranes, or about the relationship between their dissolution and permeability. In the present study, co-amorphous glibenclamide (GBC) mixtures with two amino acids, arginine (ARG) and serine (SER), in molar ratios of 1:1 were prepared by cryomilling. Their dissolution and permeability properties were studied in side-by-side diffusion chambers using cell layers containing Madine Darby kidney cells overexpressing P-glycoprotein (Pgp) transporters (MDCKII-MDR1), as Pgp may influence the absorption of GBC. Furthermore, two other compounds, the flavonoid quercetin (QRT) which is a Pgp inhibitor and the surfactant, sodium lauryl sulfate (SLS), were used as excipients to investigate if they improved either passive or active diffusion of GBC. In addition, amorphous QRT and a co-amorphous mixture of GBC and QRT (1:1) were characterized with respect to their solid-state properties and physical stability. It was demonstrated that co-amorphous GBC mixtures exhibited superior dissolution properties over the corresponding physical mixtures and amorphous GBC. Furthermore, the co-amorphous GBC-ARG-SLS mixture exhibited a 9-fold increase in permeating through the MDCKII-MDR1 cell layer as compared to the corresponding physical mixture. There was a correlation between the dissolution and permeability area under curve (AUC) values, evidence that the main mechanism behind the improved permeability of co-amorphous mixtures was their improved dissolution. The simultaneous dissolution/permeation testing with side-by-side diffusion chambers and MDCKII-MDR1 cells proved to be a feasible method for evaluating the dissolution/permeation interplay of amorphous compounds.

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Characterization of systems with amino-acids and oligosaccharides as modifiers of biopharmaceutical properties of furosemide

Cited by 14 publications

References 32 publications

Development and Characterization of Eudragit®-Based Electrospun Nanofibrous Mats and Their Formulation into Nanofiber Tablets for the Modified Release of Furosemide

Development and Characterization of Eudragit®-Based Electrospun Nanofibrous Mats and Their Formulation into Nanofiber Tablets for the Modified Release of Furosemide

Co-amorphization Story of Furosemide-Amino Acid Systems: Protonation and Aromatic Stacking Insights for Promoting Compatibility and Stability

The effect of co-amorphization of glibenclamide on its dissolution properties and permeability through an MDCKII-MDR1 cell layer

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