The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid

Fang, Liang; Numajiri, Sachihiko; Kobayashi, Daisuke; Morimoto, Yasunori

doi:10.1016/s0378-5173(03)00320-x

Cited by 41 publications

(32 citation statements)

References 33 publications

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“…1 -5 Some reports have indicated 6,7 that if the aromatic group in penicillin and cephalosporin antibiotics is replaced by the ferrocenyl moiety, bactericidal properties are significantly increased. Some studies have also indicated the bio-activity of ethanolamine against neurodegenerative diseases, 8 its antifungal, 9 cytotoxic, 10 antiinflammatory, 11 antioxidant 11 and transdermal effects, 12 and its capability of antagonizing calcium-sensing receptors. 13 Keeping in view the biological applications of ferrocene *Correspondence to: Zahid H. Chohan, Department of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan.…”

Section: Introductionmentioning

confidence: 99%

Organometallic based biologically active compounds: synthesis of mono‐ and di‐ethanolamine derived ferrocenes with antibacterial, antifungal and cytotoxic properties

Chohan¹,

Naseer²

2007

Applied Organom Chemis

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Section: Introductionmentioning

confidence: 99%

Organometallic based biologically active compounds: synthesis of mono‐ and di‐ethanolamine derived ferrocenes with antibacterial, antifungal and cytotoxic properties

Chohan¹,

Naseer²

2007

Applied Organom Chemis

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“…These penetration enhancers are chemicals that partition themselves into skin, interfere with the constituents of the skin layers and reduce the skin resistance for drug diffusion but may also lead to undesirable effects such as skin irritation, rashes and discomfort (8,9). Salt formation has been considered as an alternative strategy for the delivery of such drugs as it enhances skin permeation of these drugs without modifying the molecular structure of the active parent drug (10). Masking of the polar carboxylic acid functional group of the NSAIDs via esterification has been investigated as a promising strategy of increasing the dermal permeation.…”

Section: Introductionmentioning

confidence: 99%

Potential of Piperazinylalkylester Prodrugs of 6-Methoxy-2-Naphthylacetic Acid (6-MNA) for Percutaneous Drug Delivery

et al. 2014

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Abstract. Piperazinylalkyl ester prodrugs (4a-5d) of 6-methoxy-2-naphthylacetic acid (6-MNA) (1) were synthesized and evaluated in vitro for the purpose of percutaneous drug delivery. These ionizable prodrugs exhibited varying aqueous solubilities and lipophilicities depending on the pH of the medium. The prodrugs (4a-5c) showed higher aqueous solubility and similar lipophilicity at pH 5.0 and lower aqueous solubility and higher lipophilicity at pH 7.4 in comparison to 6-MNA. The chemical and enzymatic hydrolyses of the prodrugs was investigated in aqueous buffer solutions (pH 5.0 and 7.4) and in 80% human serum (pH 7.4) at 37°C. The prodrugs showed moderate chemical stability (t 1/2 =6-60 h) but got readily hydrolyzed enzymatically to 6-MNA with half-life ranging from 10-60 min. In the in vitro permeation study using rat skin, the flux of 6-MNA and the prodrugs was determined in aqueous buffers of pH 5.0 and 7.4. The prodrug (5b) showed 7.9-and 11.2-fold enhancement in skin permeation compared to 6-MNA (1) at pH 5.0 and 7.4, respectively. It was concluded that the parent NSAIDs having favorable pharmacokinetic and pharmacodynamic properties coupled with increased skin permeability of their prodrugs could give better options for the treatment of rheumatic diseases.

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“…Studies have shown that an ion pair behaves as one unit in determining the penetration behavior. By varying counter ions, the ion pair interaction has a direct effect on the physicochemical properties of permeants, such as solubility (Cheong & Choi, 2002), lipophilicity (Fang et al, 2003), conductivity (Hatanaka et al, 2000), melting point (Dimas et al, 2005), and hydrogen bonding potential (Cui et al, 2015). The diversity is beneficial to a flexible formulation design.…”

Section: Introductionmentioning

confidence: 99%

Development of a drug-in-adhesive patch combining ion pair and chemical enhancer strategy for transdermal delivery of zaltoprofen: pharmacokinetic, pharmacodynamic and in vitro/in vivo correlation evaluation

et al. 2016

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The aim of the study was to develop a drug-in-adhesive patch system for transdermal delivery of zaltoprofen (ZAL). The formulation was designed in combination with the ion pair and chemical enhancer strategy. Seven organic amines were chosen as counter ions, and the prepared ion pairs were characterized by Fourier transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). The in vivo pharmacokinetic performance of ZAL was studied on rabbits following transdermal and intravenous administration. A deconvolution method was applied to determine the correlation between the in vitro permeation and the in vivo absorption. Acetic acid-induced writhing response was conducted on mice to evaluate the analgesic effect. In vitro permeation results showed that both ion pairs and chemical enhancers were effective in modulating ZAL skin permeation from patches. The enhancement ratio was negatively correlated to the polar surface area (PSA) of counter ions, and was positively correlated to the octanol-water partition coefficient (log K o/w ) of chemical enhancers, respectively. The optimized formulation contained 10% (w/w) ZAL-triethylamine and 10% (w/w) isopropyl myristate, with DURO-TAK Õ 87-4098 as the pressure sensitive adhesive matrix. Furthermore, the in vitro permeation data were well correlated with the in vivo absorption data. The analgesic effect of the optimized patch was comparable to the commercial indometacin plasters. In conclusion, it was feasible for transdermal delivery of ZAL by the synergistic action of ion pair and chemical enhancer, and the in vitro permeation data were indicative of the in vivo performance for the developed patches. KeywordsIon pair, in vitro/in vivo correlation, pharmacokinetic, transdermal, zaltoprofen History

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The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid

Cited by 41 publications

References 33 publications

Organometallic based biologically active compounds: synthesis of mono‐ and di‐ethanolamine derived ferrocenes with antibacterial, antifungal and cytotoxic properties

Organometallic based biologically active compounds: synthesis of mono‐ and di‐ethanolamine derived ferrocenes with antibacterial, antifungal and cytotoxic properties

Potential of Piperazinylalkylester Prodrugs of 6-Methoxy-2-Naphthylacetic Acid (6-MNA) for Percutaneous Drug Delivery

Development of a drug-in-adhesive patch combining ion pair and chemical enhancer strategy for transdermal delivery of zaltoprofen: pharmacokinetic, pharmacodynamic and in vitro/in vivo correlation evaluation

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