Permeability of Ibuprofen in the Form of Free Acid and Salts of L-Valine Alkyl Esters from a Hydrogel Formulation through Strat-M™ Membrane and Human Skin

Klebeko, Joanna; Ossowicz‐Rupniewska, Paula; Nowak, Anna; Januś, Ewa; Duchnik, Wiktoria; Adamiak-Giera, Urszula; Kucharski, Łukasz; Prowans, Piotr; Petriczko, Jan; Czapla, Norbert; Bargiel, Piotr; Markowska, Marta; Klimowicz, Adam

doi:10.3390/ma14216678

Cited by 20 publications

(11 citation statements)

References 33 publications

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“…Thus, in this research, a facile single-fluid blending electrospinning process was combined with the casting film method to fabricate a medicated double-layer hybrid for providing a dual-phase drug controlled release profile. Ibuprofen (IBU), a highly effective antipyretic and analgesic drug, and also a typical poorly water-soluble drug [ 69 , 70 ], was selected as a drug model. Two very common polymeric excipients, water-soluble polyvinylpyrrolidone (PVP) and water-insoluble ethyl cellulose (EC), were selected as drug carriers to show the combination of electrospinning and casting, and to offer a desired two-stage IBU release profile.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Films Prepared from a Combination of Electrospinning and Casting for Offering a Dual-Phase Drug Release

et al. 2022

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One of the most important trends in developments in electrospinning is to combine itself with traditional materials production and transformation methods to take advantage of the unique properties of nanofibers. In this research, the single-fluid blending electrospinning process was combined with the casting film method to fabricate a medicated double-layer hybrid to provide a dual-phase drug controlled release profile, with ibuprofen (IBU) as a common model of a poorly water-soluble drug and ethyl cellulose (EC) and polyvinylpyrrolidone (PVP) K60 as the polymeric excipients. Electrospun medicated IBU-PVP nanofibers (F7), casting IBU-EC films (F8) and the double-layer hybrid films (DHFs, F9) with one layer of electrospun nanofibers containing IBU and PVP and the other layer of casting films containing IBU, EC and PVP, were prepared successfully. The SEM assessments demonstrated that F7 were in linear morphologies without beads or spindles, F8 were solid films, and F9 were composed of one porous fibrous layer and one solid layer. XRD and FTIR results verified that both EC and PVP were compatible with IBU. In vitro dissolution tests indicated that F7 were able to provide a pulsatile IBU release, F8 offered a typical drug sustained release, whereas F9 were able to exhibit a dual-phase controlled release with 40.3 ± 5.1% in the first phase for a pulsatile manner and the residues were released in an extended manner in the second phase. The DHFs from a combination of electrospinning and the casting method pave a new way for developing novel functional materials.

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Section: Introductionmentioning

confidence: 99%

Hybrid Films Prepared from a Combination of Electrospinning and Casting for Offering a Dual-Phase Drug Release

et al. 2022

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“…For this research, skin samples with impedance >3 kΩ were used, which corresponds to the electrical resistance of human skin [29]. Skin impedance was measured out analogously as described previously [30].…”

Section: In Vitro Penetration Studies Through Human Skin and A Transdermal Diffusion Test Modelmentioning

confidence: 99%

Assessment of the Effect of Structural Modification of Ibuprofen on the Penetration of Ibuprofen from Pentravan® (Semisolid) Formulation Using Human Skin and a Transdermal Diffusion Test Model

Ossowicz-Rupniewska,

Nowak,

Klebeko

et al. 2021

Materials

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The effect of transdermal vehicle (Pentravan®) on skin permeability was examined for unmodified ibuprofen (IBU) and ion pairs of ibuprofen with new L-valine alkyl esters [ValOR][IBU]. The percutaneous permeation across the human skin and transdermal diffusion test model (Strat-M® membranes) of ibuprofen and its structural modification were measured and compared using Franz diffusion cells. For comparison, the penetration of ibuprofen from a commercial product was also investigated. The cumulative amount of drug permeated through human skin at the end of the 24 h study was highest for ibuprofen derivatives containing propyl (C3), isopropyl (C3), ethyl (C2), and butyl (C4) esters. For Strat-M®, the best results were obtained with the alkyl chain length of the ester from C2 to C5. The permeation profiles and parameters were appointed, such as steady-state flux, lag time, and permeability coefficient. It has been shown that L-valine alkyl ester ibuprofenates, with the propyl, butyl, and amyl chain, exhibit a higher permeation rate than ibuprofen. The diffusion parameters of analyzed drugs through human skin and Strat-M® were similar and with good correlation. The resulting Pentravan-based creams with ibuprofen in the form of an ionic pair represent a potential alternative to other forms of the drug-containing analgesics administered transdermally. Furthermore, the Strat-M® membranes can be used to assess the permeation of transdermal preparations containing anti-inflammatory drugs.

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“…Recent research on TDDS with ibuprofen focuses mainly on the use of a chemical modification of the structure of ibuprofen [ 4 , 11 , 12 , 13 ] and the use of permeation enhancers (such as short-chain alcohols or light mineral oil as a lipophilic vehicle) or crystallization inhibitors that will increase the penetration of the drug through the skin and extend the shelf life of the patches [ 14 , 15 , 16 ]. In addition, research has been carried out in terms of the mechanism of transdermal penetration of drug molecules with respect to their physicochemical properties, such as solubility (S), the presence of enantiomer (ET), the logarithm of the octanol-water partition coefficient (log P), molecular weight (MW), and melting point (MP) [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Structural Modification of Ibuprofen on the Penetration Release of Ibuprofen from a Drug-in-Adhesive Matrix Type Transdermal Patch

Ossowicz‐Rupniewska

Bednarczyk

Nowak

et al. 2022

IJMS

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This study aimed to evaluate the effect of chemical modifications of the structure of active compounds on the skin permeation and accumulation of ibuprofen [IBU] from the acrylic pressure-sensitive adhesive used as a drug-in-adhesives matrix type transdermal patch. The active substances tested were ibuprofen salts obtained by pairing the ibuprofen anion with organic cations, such as amino acid isopropyl esters. The structural modification of ibuprofen tested were Ibuprofen sodium salt, [GlyOiPr][IBU], [AlaOiPr][IBU], [ValOiPr][IBU], [SerOiPr][IBU], [ThrOiPr][IBU], [(AspOiPr)2][IBU], [LysOiPr][IBU], [LysOiPr][IBU]2, [PheOiPr][IBU], and [ProOiPr][IBU]. For comparison, the penetration of unmodified ibuprofen and commercially available patches was also investigated. Thus, twelve transdermal patches with new drug modifications have been developed whose adhesive carrier is an acrylate copolymer. The obtained patches were characterized for their adhesive properties and tested for permeability of the active substance. Our results show that the obtained ibuprofen patches demonstrate similar permeability to commercial patches compared to those with structural modifications of ibuprofen. However, these modified patches show an increased drug permeability of 2.3 to even 6.4 times greater than unmodified ibuprofen. Increasing the permeability of the active substance and properties such as adhesion, cohesion, and tack make the obtained patches an excellent alternative to commercial patches containing ibuprofen.

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Permeability of Ibuprofen in the Form of Free Acid and Salts of L-Valine Alkyl Esters from a Hydrogel Formulation through Strat-M™ Membrane and Human Skin

Cited by 20 publications

References 33 publications

Hybrid Films Prepared from a Combination of Electrospinning and Casting for Offering a Dual-Phase Drug Release

Hybrid Films Prepared from a Combination of Electrospinning and Casting for Offering a Dual-Phase Drug Release

Assessment of the Effect of Structural Modification of Ibuprofen on the Penetration of Ibuprofen from Pentravan® (Semisolid) Formulation Using Human Skin and a Transdermal Diffusion Test Model

Evaluation of the Structural Modification of Ibuprofen on the Penetration Release of Ibuprofen from a Drug-in-Adhesive Matrix Type Transdermal Patch

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