Stabilization of the Metastable α–Form of Indomethacin Induced by the Addition of 2-Hydroxypropyl-β-Cyclodextrin, Causing Supersaturation (Spring) and Its Sustaining Deployment (Parachute)

Wada-Hirai, Ayako; Shimizu, Shota; Ichii, Risa; Tsunoda, Chihiro; Hiroshige, Ryosuke; Fujita, Momoko; Li, Ying Peng; Shimada, Yohsuke; Otsuka, Yuta; Goto, Setsuko

doi:10.1016/j.xphs.2021.07.002

Cited by 13 publications

(29 citation statements)

References 34 publications

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“…Other investigators have observed that drug/CD complexes both enhance the rate of drug dissolution and stabilize the supersaturated drug solution formed from about 0.5 to about 12 h [ 102 , 103 , 104 ]. The influence of CDs on drug dissolution has been referred to as the spring (i.e., fast dissolution) and parachute (i.e., stabilization of supersaturated drug solution) effect [ 105 , 106 ].…”

Section: The Anomalous Properties Of Cyclodextrinsmentioning

confidence: 99%

Anomalous Properties of Cyclodextrins and Their Complexes in Aqueous Solutions

2023

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Cyclodextrins (CDs) are cyclic oligosaccharides that emerged as industrial excipients in the early 1970s and are currently found in at least 130 marketed pharmaceutical products, in addition to numerous other consumer products. Although CDs have been the subject of close to 100,000 publications since their discovery, and although their structure and properties appear to be trivial, CDs are constantly surprising investigators by their unique physicochemical properties. In aqueous solutions, CDs are solubilizing complexing agents of poorly soluble drugs while they can also act as organic cosolvents like ethanol. CDs and their complexes self-assemble in aqueous solutions to form both nano- and microparticles. The nanoparticles have diameters that are well below the wavelength of visible light; thus, the solutions appear to be clear. However, the nanoparticles can result in erroneous conclusions and misinterpretations of experimental results. CDs can act as penetration enhancers, increasing drug permeation through lipophilic membranes, but they do so without affecting the membrane barrier. This review is an account of some of the unexpected results the authors have encountered during their studies of CDs as pharmaceutical excipients.

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Section: The Anomalous Properties Of Cyclodextrinsmentioning

confidence: 99%

Anomalous Properties of Cyclodextrins and Their Complexes in Aqueous Solutions

2023

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“…The intermedial peak indicated the phase transition from the metastable a-form to the most stable g-form. 50 In Fig. 1B, the DSC thermograms of the DCF/b-CD mixtures show the endothermic signal at a dropping temperature of about 445-447 K except for that of the plain b-CD (0 : 1).…”

Section: Preparation Of Acidic Api Complexes With B-cd and Their Diff...mentioning

confidence: 90%

“…The SM-prepared mixtures were provided in molar ratios (mole fraction of API) of 1 : 0 (100%), 3 : 1 (75%), 2 : 1 (67%), 1 : 1 (50%), 1 : 2 (33%), 1 : 3 (25%), and 0 : 1 (0%). Because the SM-prepared INM/β-CD mixture induced the α-form of INM, 50 the neat INM dried in a vacuum was used as the γ-form and the α-form crystal was yielded by recrystallization with ethanol, evaporating overnight at a temperature of 278 K.…”

Section: Methodsmentioning

confidence: 99%

“…48 We recently applied the melting entropy-phase diagram approach to determine the efficiencies of the inclusion complexation of INM with HP-β-CD for mixtures prepared using the physical mixture (PM) method and those prepared using the solution mixture (SM) method. 50 We considered that these complexes contained independent molecules with single polymorphs. Therefore, for transformation among the polymorphs, we analyzed their DSC thermograms using rough approximations.…”

Section: Introductionmentioning

confidence: 99%

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Using singular value decomposition to analyze drug/β-cyclodextrin mixtures: insights from X-ray powder diffraction patterns

Hasegawa,

Goto,

Tsunoda

et al. 2023

Phys. Chem. Chem. Phys.

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“…In the study of host-guest supramolecular chemistry, absorption spectra were regularly used to verify IC formation [35,36]. Characteristics of complexes were also performed through the use of such methods as DSC [37], XRD [38,39] and NMR [40,41], with binding constants also determined [16,42]. In the present study, the absorption spectra of methanol:HCl solutions (1:9 v/v) of β-CD, IND and IC were taken into consideration for stability of medicinal compounds included in cyclodextrin.…”

Section: Stoichiometry Of Ind-β-cd Inclusion Complex In Watermentioning

confidence: 99%

Preparation and Characterization of Indomethacin Supramolecular Systems with β-Cyclodextrin in Order to Estimate Photostability Improvement

Jamrógiewicz

Józefowicz

2021

Molecules

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Cyclodextrins have found wide application in contemporary chemistry, pharmacy and medicine. Because of their unique properties, cyclodextrins are constantly used in research on solubility or stability improvement, as well as other physicochemical properties of medicinal substances. Indomethacin (IND) is a photolabile molecule that also attracts the interest of researchers due to its therapeutic potential and the need to overcome its problematic photosensitivity. Supramolecular complexes of indomethacin with β-cyclodextrin (CD) are already known, and they show greater stability compared to complexes with other types of cyclodextrins. So far, however, the sensitivity to light of physical mixtures and inclusion complexes in the solid phase has not been studied, and their various stoichiometries have not yet been investigated. Due to this fact, the aim of the present study is to obtain supramolecular systems (inclusion complexes and physical mixtures) of indomethacin with three different amounts of β-cyclodextrin. Assessment of the photochemical stability of indomethacin-β-cyclodextrin systems in the solid state is performed in order to find the best correlation between IND stability and the amount of CD. Comparative analysis of physicochemical degradation for stoichiometry systems [CD:IND] = [1:1], [0.5:1] and [0.1:1] is performed by using ultraviolet spectroscopy, transmission—FTIR, reflection—ATR-FTIR infrared spectroscopy and DSC calorimetry.

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Stabilization of the Metastable α–Form of Indomethacin Induced by the Addition of 2-Hydroxypropyl-β-Cyclodextrin, Causing Supersaturation (Spring) and Its Sustaining Deployment (Parachute)

Cited by 13 publications

References 34 publications

Anomalous Properties of Cyclodextrins and Their Complexes in Aqueous Solutions

Anomalous Properties of Cyclodextrins and Their Complexes in Aqueous Solutions

Using singular value decomposition to analyze drug/β-cyclodextrin mixtures: insights from X-ray powder diffraction patterns

Preparation and Characterization of Indomethacin Supramolecular Systems with β-Cyclodextrin in Order to Estimate Photostability Improvement

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