Efficiency of “cyclodextrin-ibuprofen” inclusion complex formation

Pereva, Stiliyana; Sarafska, Tsveta; Богданова, С. А.; Spassov, Тony

doi:10.1016/j.jddst.2016.04.006

Cited by 60 publications

(39 citation statements)

References 44 publications

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“…The latter is characterized by the formation of IbuH domanins in the pores of the 3D structure of the polymeric network. The experimental data show that the inclusion of IbuH in the CD cavity – namely the formation of a host–guest inclusion complex – does not occur, confirming the situation already described by HR-MAS NMR data for the same system in the gel state [ 9 ] and outlining a different scenario on passing from monomeric CD, capable to form well characterized inclusion complexes with IbuH [ 29 – 31 ] to CDNS of the present work. A possible explanation relies upon the availability of the CD cavity within the polymeric network.…”

Section: Discussionsupporting

confidence: 89%

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

Ferro

Castiglione

Pastori

et al. 2017

Beilstein J. Org. Chem.

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Two different formulations of cyclodextrin nanosponges (CDNS), obtained by polycondensation of β-cyclodextrin with ethylenediaminetetraacetic acid dianhydride (EDTAn), were treated with aqueous solutions of ibuprofen sodium salt (IbuNa) affording hydrogels that, after lyophilisation, gave two solid CDNS-drug formulations. 1H fast MAS NMR and 13C CP-MAS NMR spectra showed that IbuNa was converted in situ into its acidic and dimeric form (IbuH) after freeze-drying. 13C CP-MAS NMR spectra also indicated that the structure of the nanosponge did not undergo changes upon drug loading compared to the unloaded system. However, the 13C NMR spectra collected under variable contact time cross-polarization (VCT-CP) conditions showed that the polymeric scaffold CDNS changed significantly its dynamic regime on passing from the empty CDNS to the drug-loaded CDNS, thus showing that the drug encapsulation can be seen as the formation of a real supramolecular aggregate rather than a conglomerate of two solid components. Finally, the structural features obtained from the different solid-state NMR approaches reported matched the information from powder X-ray diffraction profiles.

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Section: Discussionsupporting

confidence: 89%

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

Ferro

Castiglione

Pastori

et al. 2017

Beilstein J. Org. Chem.

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“…Cyclodextrin complexes of these drugs were formulated by this method and improvement in different physicochemical properties was observed. The inclusion complex formation of cyclodextrins by kneading method has been described by encapsulation of ibuprofen, [108] Omega-3 fatty acids in thymol essential oil, [109] and European anchovy (Engraulis encrasicolus L.) oil. [110,111] …”

Section: Kneading Methodsmentioning

confidence: 99%

Untitled

Budhwar¹

2018

AJP

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Inclusion complexes have various applications in different fields of drug delivery and pharmaceutical industry due to their ability of complexation with guest molecules and enhancement of the physicochemical properties of guest molecules. Cyclodextrins and their derivatives have the ability to encapsulate the bioactive compounds into its cavity and protect these from the environmental conditions, improve the solubility, bioavailability, and other properties also. The aim of this review is to highlight the advantages of cyclodextrins in the enhancement of physicochemical properties of drugs (such as solubility, stability, bioavailability, permeability, and others), different methods for production and various characterization techniques used for evaluation of complexes. Applications of cyclodextrin complexes in pharmaceutical and other fields are also explained here with examples. Thus cyclodextrins, because of their continuing ability to find several novel applications in drug delivery, are expected to solve many problems accompanied with the delivery of different novel drugs through various delivery routes.

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“…-Phương pháp trộn vật lý (mẫu M1): Flurbiprofen và β-CD được trộn theo nguyên tắc đồng lượng bằng chày cối mã não trong 30 phút [21].…”

Section: Bào Chế Phức Hợp Flurbiprofen/βcyclodextrinunclassified

Preparation and Characterization of Flurbiprofen/β-Cyclodextrin Inclusion Complex

Bình

Xuan²,

Yen³

2020

MPS

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This study aims to ameliorate the water solubility of flurbiprofen by using β-cyclodextrin (β-CD). The drug/ligand 1:1 (M/M) stoichiometry was determined based on the effect of β-CD on the solubility of flurbiprofen. Several methods of preparing flurbiprofen/β-CD inclusion complex were investigated and a solvent method using hot water to dissolve the starting materials was selected. The selected method showed a lot of advantages such as high complexing ability, good product yield, simple and eco-friendly process. The obtained product was characterized using various analytical techniques such as high-performance liquid chromatography, differential scanning calorimetry, Fourier transform infrared spectroscopy, X-ray diffraction and scanning electron microscopy. The product had a predominantly amorphous form with clathrate particles of about 2-7 µm in size, irregular edges and rough surfaces. The study results show that in the complexing process, flurbiprofen replaced water molecules located in the conical cavity of β-CD. The complex contained 19.91% flurbiprofen by mass with water solubility at 37°C was 1,100 µg/ml. The results also show that the complexing with β-CD significantly improved the water solubility of flurbiprofen by both speed and level. Keywords Flurbiprofen, β-cyclodextrin, inclusion complex, water solubility, preparation, characterization. References [1] K. Maroof, F. Zafar, H. Ali, S. Naveed, Flurbiprofen: a potent pain reliever, J. Bioequiv. Availab. 7(1) (2015) 056-058. https://doi.org/10.4172/jbb.1000214.[2] J.J. Thebault, G. Lagrue, C.E. Blatrix, L. Cheynier, R. Cluzan, Clinical pharmacology of flurbiprofen: a novel inhibitor of platelet aggregation, Curr. Med. Res. Opin. 5(1) (1977) 130-134. https://doi.org/10.1185/03007997709108990.[3] H. Geerts, Drug evaluation: (R)-flurbiprofen - an enantiomer of flurbiprofen for the treatment of Alzheimer's disease, Idrugs. 10(2) (2007) 121-133.[4] P.L. McGeer, M. Schulzer, E.G. McGeer, Arthritis and anti-inflammatory agents as possible protective factors for Alzheimer's disease: a review of 17 epidemiologic studies, Neurology. 47(2) (1996) 425-432. https://doi.org/10.1212/WNL.47.2.425.[5] S. Meister, I. Zlatev, J. Stab, D. Docter, S. Baches, et al., Nanoparticulate flurbiprofen reduces amyloid-β 42 generation in an in vitro blood-brain barrier model, Alzheimers Res. Ther. 5(6) (2013) 51-63. https://doi.org/10.1186/alzrt225.[6] K.P. Townsend, D. Praticò, Novel therapeutic opportunities for Alzheimer’s disease: focus on nonsteroidal anti-inflammatory drugs, FASEB J. 19(12) (2005) 1592-1601. https://doi.org/10.1096/fj.04-3620rev.[7] C.K. Kim, Y.S. Yoon, J.Y. Kong, Preparation and evaluation of flurbiprofen dry elixir as a novel dosage form using a spray-drying technique, Int. J. 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Yong, Enhanced solubility and bioavailability of flurbiprofen by cycloamylose, Arch. Pharm. Res. 34 (2011) 391-397. https://doi.org/10.1007/s12272-011-0306-x.[13] A. Muraoka, T. Tokumura, Y. Machida, Evaluation of the bioavailability of flurbiprofen and its β-cyclodextrin inclusion complex in four different doses upon oral administration to rats, Eur. J. Pharm. Biopharm. 58(3) (2004) 667-671. https://doi.org/10.1016/j.ejpb.2004.03.030.[14] T. Tokumura, A. Muraoka, Y. Machida, Improvement of oral bioavailability of flurbiprofen from flurbiprofen/beta-cyclodextrin inclusion complex by action of cinnarizine, Eur. J. Pharm. Biopharm. 73 (2009) 202-204. https://doi.org/10.1016/j.ejpb.2009.04.018.[15] D. Li, M. Han, P. Balakrishnan, Y. Yan, D. Oh, et al., Enhanced oral bioavailability of flurbiprofen by combined use of micelle solution and inclusion compound, Arch. Pharm. Res. 33(1) (2010) 95-101. https://doi.org/10.1007/s12272-010-2231-9.[16] H. Arima, K. Motoyama, T. Irie, Recent findings on safety profiles of cyclodextrins, cyclodextrin conjugates, and polypseudorotaxanes, in: E. Bilensoy (Ed.), Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicine: Current and Future Industrial Applications, John Wiley & Sons Inc., Hoboken, 2011, pp. 91-122. https://doi.org/10.1002/9780470926819.ch5.[17] T.J. Grattan, Inclusion complexes of beta-cyclodextrin with flurbiprofen, ketoprofen and naproxen, International patent WO1995007104A1, March 16, 1995.[18] M. Cirri, C. Rangoni, F. Maestrelli, G. Corti, P. Mura, Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes, Drug Dev. Ind. Pharm. 31(7) (2005) 697-707. https://doi.org/10.1080/03639040500253694.[19] M. Tirunagari, N. Mehveen, M.F. Qureshi, J.P. Sultana, V. Tirunagari (2012), Solubility Enhancement of Flurbiprofen using Different Solubilization Techniques, Int. J. Pharm. Pharm. Sci. 4(4) (2012) 97-100.[20] P. Saokham, C. Muankaew, P. Jansook, T. Loftsson, Solubility of cyclodextrins and drug/cyclodextrin complexes, Molecules. 23(5) (2018) 1161-1175. https://doi.org/10.3390/molecules23051161.[21] S. Pereva, T. Sarafska, S. Bogdanova, T. Spassov, Efficiency of “cyclodextrin-ibuprofen” inclusion complex formation, J. Drug Deliv. Sci. Tec. 35 (2016) 34-39. https://doi.org/10.1016/j.jddst.2016.04.006.[22] T.T.B. Nguyen, N.A. Dang, M.A. Tran, T.H. Nguyen, Validation of a high-performance liquid chromatographic method with diod array detection for the quantification of flurbiprofen in 100 mg film-coated tablet, VNU Journal of Science: Medical and Pharmaceutical Sciences. 33(2) (2017) 41-49. https://doi.org/10.25073/2588-1132/vnumps.4085.[23] T. Higuchi, K.A. Connors, Phase-solubility techniques, Adv. Anal. Chem. Instrum. 4 (1965) 117-122.

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Efficiency of “cyclodextrin-ibuprofen” inclusion complex formation

Cited by 60 publications

References 44 publications

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

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Preparation and Characterization of Flurbiprofen/β-Cyclodextrin Inclusion Complex

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