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Evaluation of physicochemical properties, skin permeation and accumulation profiles of salicylic acid amide prodrugs as sunscreen agent.
MedLine Citation:
PMID:  21839822     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Yi-Dong Yan; Jun Ho Sung; Dong Won Lee; Jung Sun Kim; Eun-Mi Jeon; Dae-Duk Kim; Dong Wook Kim; Jong Oh Kim; Chul Soon Yong; Han Gon Choi
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-8-6
Journal Detail:
Title:  International journal of pharmaceutics     Volume:  -     ISSN:  1873-3476     ISO Abbreviation:  -     Publication Date:  2011 Aug 
Date Detail:
Created Date:  2011-8-15     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7804127     Medline TA:  Int J Pharm     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011. Published by Elsevier B.V.
Affiliation:
College of Pharmacy, Yeungnam University, 214-1 Dae-Dong, Gyungsan, Gyungbuk 712-749, South Korea.
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