Improved transdermal delivery of prostaglandin E1 through hairless mouse skin: combined use of carboxymethyl-ethyl-β-cyclodextrin and penetration enhancers

Uekama, Kaneto; Adachi, Hirotoshi; Irie, Tetsumi; Yano, Tadanori; Saita, Masaru; Noda, Kanji

doi:10.1111/j.2042-7158.1992.tb03574.x

Cited by 45 publications

(11 citation statements)

References 11 publications

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“…Acitretin RMbCD [21] Alkannin HPbCD [22] Avobenzone HPbCD [23] Beclometasone dipropionate gCD [24] 4-Biphenylylacetic acid bCD, DMbCD, HPbCD [25,26] Bupranolol HPbCD, MbCD [27] Capsaicin HPbCD [28] Celecoxib DMbCD [29] Curcumin HPbCD, HPgCD [30] Dexamethasone acetate bCD, HPbCD [31] 17b-Estradiol HPbCD [32] Hydrocortisone bCD, CMbCD, HPbCD, MLbCD, RMbCD [32][33][34][35][36][37][38][39] Ibuprofen HPbCD [40] Indometacin bCD, DEbCD, DMbCD [41,42] Ketoprofen HPbCD [43] Liarozole HPbCD [44] Lidocaine DMbCD, HPbCD, SBEbCD [45] Loteprednol etabonate DMbCD [46] Melatonin HPbCD [47] Metopimazine MbCD [48] Methyl paraben HPbCD [49] Miconazole aCD, HPbCD [50] Naproxen bCD [51] Piribedil RMbCD [52] Piroxicam HPbCD [53,54] Prednisolone bCD, gCD [55] Prostaglandin E1 aCD, bCD, CMEbCD, [56][57][58][59] Shikonin HPbCD [22] Sulfanilic acid bCD, DMbCD [41] Testosterone HPbCD [32] Tolnaftate bCD, bCD-polymer [60] Tretinoin bCD, H...…”

Section: Drugmentioning

confidence: 99%

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Loftsson

Brewster

2011

Journal of Pharmacy and Pharmacology

243

126

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Objectives Cyclodextrins are useful solubilizing excipients that have gained currency in the formulator's armamentarium based on their ability to temporarily camouflage undesirable physicochemical properties. In this context cyclodextrins can increase oral bioavailability, stabilize compounds to chemical and enzymatic degradation and can affect permeability through biological membranes under certain circumstances. This latter property is examined herein as a function of the published literature as well as work completed in our laboratories. Key findings Cyclodextrins can increase the uptake of drugs through biological barriers if the limiting barrier component is the unstirred water layer (UWL) that exists between the membrane and bulk water. This means that cyclodextrins are most useful when they interact with lipophiles in systems where such an UWL is present and contributes significantly to the barrier properties of the membrane. Furthermore, these principles are used to direct the optimal formulation of drugs in cyclodextrins. A second related critical success factor in the formulation of cyclodextrin-based drug product is an understanding of the kinetics and thermodynamics of complexation and the need to optimize the cyclodextrin amount and drug-to-cyclodextrin ratios. Drug formulations, especially those targeting compartments associated with limited dissolution (i.e. the eye, subcutaneous space, etc.), should be carefully designed such that the thermodynamic activity of the drug in the formulation is optimal meaning that there is sufficient cyclodextrin to solubilize the drug but not more than that. Increasing the cyclodextrin concentration decreases the formulation 'push' and may reduce the bioavailability of the system. Conclusions A mechanism-based understanding of cyclodextrin complexation is essential for the appropriate formulation of contemporary drug candidates.

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Section: Drugmentioning

confidence: 99%

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Loftsson

Brewster

2011

Journal of Pharmacy and Pharmacology

243

126

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“…to release the included drug, [122][123][124][125][126] 5) inhibition of the P-gp-mediated efflux of drug from intestinal epithelial cells. 71,72) In this section, factors affecting the drug absorption by hydrophilic CyDs will be discussed.…”

Section: Enhancement Of Drug Absorption By Hydrophilic Cydsmentioning

confidence: 99%

Design and Evaluation of Cyclodextrin-Based Drug Formulation

2004

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“…Many groups of chemicals are known to enhance the absorption of drugs through the stratum corneum (17,18). One group of successful penetration enhancers are the azacycloalkane derivatives, like 1-[2-(decylthio)ethyl]azacyclopentan-2one (HPE-101) and Azone (17,18,(21)(22)(23)(24)(25). The mechanism of penetration enhancement of the azacycloalkane derivatives has been thoroughly investigated with Azone (18,23,25).…”

Section: Introductionmentioning

confidence: 99%

Topical Application of 5-Aminolevulinic Acid Hexyl Ester and 5-Aminolevulinic Acid to Normal Nude Mouse Skin: Differences in Protoporphyrin IX Fluorescence Kinetics and the Role of the Stratum Corneum¶

Akker

Iani

Star

et al. 2000

Photochemistry and Photobiology

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An important limitation of topical 5‐aminolevulinic acid (ALA)‐based photodetection and photodynamic therapy is that the amount of the fluorescing and photosensitizing product protoporphyrin IX (PpIX) formed is limited. The reason for this is probably the limited diffusion of ALA through the stratum corneum. A solution to this problem might be found in the use of ALA derivatives, as these compounds are more lipophilic and therefore might have better penetration properties than ALA itself. Previous studies have shown that ALA hexyl ester (ALAHE) is more successful than ALA for photodetection of early (pre)malignant lesions in the bladder. However, ALA pentyl ester slightly increased the in vivo PpIX fluorescence in early (pre)malignant lesions in hairless mouse skin compared to ALA. The increased PpIX fluorescence is located in the stratum corneum and not in the dysplastic epidermal layer. In the present study, ALA‐ and ALAHE‐induced PpIX fluorescence kinetics are compared in the normal nude mouse skin, of which the permeability properties differ from the bladder. Application times and ALA(HE) concentrations were varied, the effect of a penetration enhancer and the effect of tape stripping the skin before or after application were investigated. Only during application for 24 h, did ALAHE induce slightly more PpIX fluorescence than ALA. After application times ranging from 1 to 60 min, ALA‐induced PpIX fluorescence was higher than ALAHE‐induced PpIX fluorescence. ALA also induced higher PpIX production than ALAHE after 10 min of application with concentrations ranging from 0.5 to 40%. The results of experiments with the penetration enhancer and tape stripping indicated that the stratum corneum acts a barrier against ALA and ALAHE. Use of penetration enhancer or tape stripping enhanced the PpIX production more in the case of ALAHE application than in the case of ALA application. This, together with the results from the different application times and concentrations indicates that ALAHE diffuses more slowly across the stratum corneum than ALA.

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Improved transdermal delivery of prostaglandin E1 through hairless mouse skin: combined use of carboxymethyl-ethyl-β-cyclodextrin and penetration enhancers

Cited by 45 publications

References 11 publications

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Design and Evaluation of Cyclodextrin-Based Drug Formulation

Topical Application of 5-Aminolevulinic Acid Hexyl Ester and 5-Aminolevulinic Acid to Normal Nude Mouse Skin: Differences in Protoporphyrin IX Fluorescence Kinetics and the Role of the Stratum Corneum¶

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