Evaluation of physicochemical properties, skin permeation and accumulation profiles of salicylic acid amide prodrugs as sunscreen agent
| Autor: | Dong Won Lee, Jong Oh Kim, Jungsun Kim, Chul Soon Yong, Dong Wuk Kim, Jun Ho Sung, Eun-Mi Jeon, Dae-Duk Kim, Dong Xun Li, Han-Gon Choi, Yi-Dong Yan, Ming Guan Piao |
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| Rok vydání: | 2011 |
| Předmět: |
Skin Absorption
Pharmaceutical Science Salicylamide In Vitro Techniques Administration Cutaneous Permeability Mice chemistry.chemical_compound Drug Stability Amide Stratum corneum medicine Animals Prodrugs Solubility Skin Mice Hairless Chromatography integumentary system Permeation Prodrug Amides Salicylates medicine.anatomical_structure Liver chemistry Lipophilicity Sunscreening Agents Salicylic acid medicine.drug |
| Zdroj: | International Journal of Pharmaceutics. 419:154-160 |
| ISSN: | 0378-5173 |
| DOI: | 10.1016/j.ijpharm.2011.07.043 |
| Popis: | Various amide prodrugs of salicylic acid were synthesised, and their physicochemical properties including lipophilicity, chemical stability and enzymatic hydrolysis were investigated. In vivo skin permeation and accumulation profiles were also evaluated using a combination of common permeation enhancing techniques such as the use of a supersaturated solution of permeants in an enhancer vehicle, a lipophilic receptor solution, removal of the stratum corneum and delipidisation of skin. Their capacity factor values were proportional to the degree of carbon-carbon saturation in the side chain. All these amides were highly stable in acetonitrile and glycerine. Amide prodrugs were converted to salicylic acid both in hairless mouse liver and skin homogenates. N-dodecyl salicylamide (C12SM) showed the lowest permeation of salicylic acid in skin compared to the other prodrugs, probably due to its low aqueous solubility. It had a high affinity for the stratum corneum and its accumulation was restricted to only the uppermost layer of skin. Thus, this amide prodrug could be a safer topical sunscreen agent with minimum potential for systemic absorption. |
| Databáze: | OpenAIRE |
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