Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation
Abstract The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate we...
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| Veröffentlicht in: | Drug delivery 2015-05, Vol.22 (3), p.359-366 |
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| creator | Pawar, Vijay Kumar, H. Yogish Giridhar, Rajani Yadav, Mange Ram |
| description | Abstract
The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate well into synovial fluid. The physicochemical properties of 6-MNA salts were investigated by solubility measurements, differential scanning calorimetry (DSC) and infrared (IR). The DSC thermograms and Fourier transform infrared (FT-IR) spectra indicated that 6-MNA formed salts with organic and alkali metal bases. Among the series, salts formed with amine bases (ethanolamine, diethanolamine, triethanolamine and diethylamine) had lower melting points while alkali metal salt (sodium) had higher melting point than 6-MNA. The salts had higher solubilities than 6-MNA as determined in phosphate buffer at pH 5.0 and 7.4. There is no significant difference in partition coefficient (log P) values between salts and 6-MNA at pH 5.0 but, at pH 7.4, the log P values for the salts increased by 4-10 times as compared to 6-MNA. In vitro permeation studies showed that all the salts increased the flux in comparision to 6-MNA, and the ethanolamine salt (1b) was found to be having 7.7 and 9.4 times higher permeability as compared to 6-MNA at pH 5.0 and 7.4, respectively. |
| doi_str_mv | 10.3109/10717544.2014.894595 |
| format | Article |
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The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate well into synovial fluid. The physicochemical properties of 6-MNA salts were investigated by solubility measurements, differential scanning calorimetry (DSC) and infrared (IR). The DSC thermograms and Fourier transform infrared (FT-IR) spectra indicated that 6-MNA formed salts with organic and alkali metal bases. Among the series, salts formed with amine bases (ethanolamine, diethanolamine, triethanolamine and diethylamine) had lower melting points while alkali metal salt (sodium) had higher melting point than 6-MNA. The salts had higher solubilities than 6-MNA as determined in phosphate buffer at pH 5.0 and 7.4. There is no significant difference in partition coefficient (log P) values between salts and 6-MNA at pH 5.0 but, at pH 7.4, the log P values for the salts increased by 4-10 times as compared to 6-MNA. In vitro permeation studies showed that all the salts increased the flux in comparision to 6-MNA, and the ethanolamine salt (1b) was found to be having 7.7 and 9.4 times higher permeability as compared to 6-MNA at pH 5.0 and 7.4, respectively.</description><identifier>ISSN: 1071-7544</identifier><identifier>EISSN: 1521-0464</identifier><identifier>DOI: 10.3109/10717544.2014.894595</identifier><identifier>PMID: 24670100</identifier><language>eng</language><publisher>England: Informa Healthcare USA, Inc</publisher><subject>6-MNA ; Anti-Inflammatory Agents, Non-Steroidal - administration & dosage ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacokinetics ; Cadaver ; Drug Carriers - chemistry ; Drug Carriers - pharmacology ; Half-Life ; Humans ; lipophilicity ; Molecular Structure ; Naphthaleneacetic Acids - administration & dosage ; Naphthaleneacetic Acids - chemistry ; Naphthaleneacetic Acids - pharmacokinetics ; NSAID ; Permeability ; Salts ; Skin - metabolism ; Skin Absorption - drug effects ; skin permeation ; Solubility</subject><ispartof>Drug delivery, 2015-05, Vol.22 (3), p.359-366</ispartof><rights>2014 Informa Healthcare USA, Inc. All rights reserved: reproduction in whole or part not permitted 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c464t-d6f9f6df1de48a796bc12735648451638b18c9ed507bdefd1794fb51fe3c2d283</citedby><cites>FETCH-LOGICAL-c464t-d6f9f6df1de48a796bc12735648451638b18c9ed507bdefd1794fb51fe3c2d283</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24670100$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pawar, Vijay</creatorcontrib><creatorcontrib>Kumar, H. Yogish</creatorcontrib><creatorcontrib>Giridhar, Rajani</creatorcontrib><creatorcontrib>Yadav, Mange Ram</creatorcontrib><title>Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation</title><title>Drug delivery</title><addtitle>Drug Deliv</addtitle><description>Abstract
The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate well into synovial fluid. The physicochemical properties of 6-MNA salts were investigated by solubility measurements, differential scanning calorimetry (DSC) and infrared (IR). The DSC thermograms and Fourier transform infrared (FT-IR) spectra indicated that 6-MNA formed salts with organic and alkali metal bases. Among the series, salts formed with amine bases (ethanolamine, diethanolamine, triethanolamine and diethylamine) had lower melting points while alkali metal salt (sodium) had higher melting point than 6-MNA. The salts had higher solubilities than 6-MNA as determined in phosphate buffer at pH 5.0 and 7.4. There is no significant difference in partition coefficient (log P) values between salts and 6-MNA at pH 5.0 but, at pH 7.4, the log P values for the salts increased by 4-10 times as compared to 6-MNA. In vitro permeation studies showed that all the salts increased the flux in comparision to 6-MNA, and the ethanolamine salt (1b) was found to be having 7.7 and 9.4 times higher permeability as compared to 6-MNA at pH 5.0 and 7.4, respectively.</description><subject>6-MNA</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacokinetics</subject><subject>Cadaver</subject><subject>Drug Carriers - chemistry</subject><subject>Drug Carriers - pharmacology</subject><subject>Half-Life</subject><subject>Humans</subject><subject>lipophilicity</subject><subject>Molecular Structure</subject><subject>Naphthaleneacetic Acids - administration & dosage</subject><subject>Naphthaleneacetic Acids - chemistry</subject><subject>Naphthaleneacetic Acids - pharmacokinetics</subject><subject>NSAID</subject><subject>Permeability</subject><subject>Salts</subject><subject>Skin - metabolism</subject><subject>Skin Absorption - drug effects</subject><subject>skin permeation</subject><subject>Solubility</subject><issn>1071-7544</issn><issn>1521-0464</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1P3DAQhq2qVdku_QcVyrGXbD2JP5ILqEJAK23FBc6WY4-VLEm82FnR_Pt6P0DqhZN9eN53Zh5CvgFdlUDrH0AlSM7YqqDAVlXNeM0_kAXwAnLKBPuY_gnJ98wZ-RLjhlJaQcE_k7OCCUmB0gX5czO2ejRos_jUjdkWw4B66vyYeZeJfMCp9X_nvMhHvW2ndu61wakzmTadzZo5i7qfMufDcAidk09O9xG_nt4leby9ebj-la_v735f_1znJi025Va42gnrwCKrtKxFY6CQJResYhxEWTVQmRotp7Kx6CzImrmGg8PSFLaoyiX5fuzdBv-8wzipoYsG-16P6HdRgai4ZKKUZULZETXBxxjQqW3oBh1mBVTtRapXkWovUh1FptjFacKuGdC-hV7NJeDqCHTj4fwXH3qrJj33PriQlHZxX__uiMv_GlpMLlujA6qN34UxCXx_x38H5ZU4</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Pawar, Vijay</creator><creator>Kumar, H. Yogish</creator><creator>Giridhar, Rajani</creator><creator>Yadav, Mange Ram</creator><general>Informa Healthcare USA, Inc</general><general>Informa Healthcare</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150501</creationdate><title>Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation</title><author>Pawar, Vijay ; Kumar, H. Yogish ; Giridhar, Rajani ; Yadav, Mange Ram</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c464t-d6f9f6df1de48a796bc12735648451638b18c9ed507bdefd1794fb51fe3c2d283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>6-MNA</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacokinetics</topic><topic>Cadaver</topic><topic>Drug Carriers - chemistry</topic><topic>Drug Carriers - pharmacology</topic><topic>Half-Life</topic><topic>Humans</topic><topic>lipophilicity</topic><topic>Molecular Structure</topic><topic>Naphthaleneacetic Acids - administration & dosage</topic><topic>Naphthaleneacetic Acids - chemistry</topic><topic>Naphthaleneacetic Acids - pharmacokinetics</topic><topic>NSAID</topic><topic>Permeability</topic><topic>Salts</topic><topic>Skin - metabolism</topic><topic>Skin Absorption - drug effects</topic><topic>skin permeation</topic><topic>Solubility</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pawar, Vijay</creatorcontrib><creatorcontrib>Kumar, H. Yogish</creatorcontrib><creatorcontrib>Giridhar, Rajani</creatorcontrib><creatorcontrib>Yadav, Mange Ram</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Drug delivery</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pawar, Vijay</au><au>Kumar, H. Yogish</au><au>Giridhar, Rajani</au><au>Yadav, Mange Ram</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation</atitle><jtitle>Drug delivery</jtitle><addtitle>Drug Deliv</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>22</volume><issue>3</issue><spage>359</spage><epage>366</epage><pages>359-366</pages><issn>1071-7544</issn><eissn>1521-0464</eissn><abstract>Abstract
The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate well into synovial fluid. The physicochemical properties of 6-MNA salts were investigated by solubility measurements, differential scanning calorimetry (DSC) and infrared (IR). The DSC thermograms and Fourier transform infrared (FT-IR) spectra indicated that 6-MNA formed salts with organic and alkali metal bases. Among the series, salts formed with amine bases (ethanolamine, diethanolamine, triethanolamine and diethylamine) had lower melting points while alkali metal salt (sodium) had higher melting point than 6-MNA. The salts had higher solubilities than 6-MNA as determined in phosphate buffer at pH 5.0 and 7.4. There is no significant difference in partition coefficient (log P) values between salts and 6-MNA at pH 5.0 but, at pH 7.4, the log P values for the salts increased by 4-10 times as compared to 6-MNA. In vitro permeation studies showed that all the salts increased the flux in comparision to 6-MNA, and the ethanolamine salt (1b) was found to be having 7.7 and 9.4 times higher permeability as compared to 6-MNA at pH 5.0 and 7.4, respectively.</abstract><cop>England</cop><pub>Informa Healthcare USA, Inc</pub><pmid>24670100</pmid><doi>10.3109/10717544.2014.894595</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 6-MNA Anti-Inflammatory Agents, Non-Steroidal - administration & dosage Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacokinetics Cadaver Drug Carriers - chemistry Drug Carriers - pharmacology Half-Life Humans lipophilicity Molecular Structure Naphthaleneacetic Acids - administration & dosage Naphthaleneacetic Acids - chemistry Naphthaleneacetic Acids - pharmacokinetics NSAID Permeability Salts Skin - metabolism Skin Absorption - drug effects skin permeation Solubility |
| title | Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation |
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