Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone
The biodegradable transdermal penetration enhancer, dodecyl 2-(N,N-dimethylamino)propionate (II; DDAIP), was prepared by reacting dodecyl 2-bromopropionate (I), obtained by reaction of n-dodecanol with 2-bromopropionyl halogenide, with dimethylamine. The penetration enhancing effects of DDAIP on the...
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| Veröffentlicht in: | Pharmaceutical research 1993-11, Vol.10 (11), p.1632-1637 |
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| creator | BÜYÜKTIMKIN, S BÜYÜKTIMKIN, N RYTTING, J. H |
| description | The biodegradable transdermal penetration enhancer, dodecyl 2-(N,N-dimethylamino)propionate (II; DDAIP), was prepared by reacting dodecyl 2-bromopropionate (I), obtained by reaction of n-dodecanol with 2-bromopropionyl halogenide, with dimethylamine. The penetration enhancing effects of DDAIP on the transport of indomethacin, clonidine, and hydrocortisone across shed snake skin (Elaphe obsoleta) were evaluated. Azone and lauryl alcohol, a possible decomposition product of DDAIP, were used as standard enhancers for comparison. In terms of flux, DDAIP showed 4.7 and 7.5 times the promoting effect for indomethacin compared to azone and lauryl alcohol, respectively. With clonidine this effect was 1.7 and 3.1 times, whereas with hydrocortisone it was 2.4 and 2.8 times higher, respectively. In vitro biodegradability of DDAIP was demonstrated in the presence of porcine esterase. The results indicate that DDAIP increases markedly the transepidermal delivery of several types of drug substances. |
| doi_str_mv | 10.1023/A:1018980905312 |
| format | Article |
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H</creator><creatorcontrib>BÜYÜKTIMKIN, S ; BÜYÜKTIMKIN, N ; RYTTING, J. H</creatorcontrib><description>The biodegradable transdermal penetration enhancer, dodecyl 2-(N,N-dimethylamino)propionate (II; DDAIP), was prepared by reacting dodecyl 2-bromopropionate (I), obtained by reaction of n-dodecanol with 2-bromopropionyl halogenide, with dimethylamine. The penetration enhancing effects of DDAIP on the transport of indomethacin, clonidine, and hydrocortisone across shed snake skin (Elaphe obsoleta) were evaluated. Azone and lauryl alcohol, a possible decomposition product of DDAIP, were used as standard enhancers for comparison. In terms of flux, DDAIP showed 4.7 and 7.5 times the promoting effect for indomethacin compared to azone and lauryl alcohol, respectively. With clonidine this effect was 1.7 and 3.1 times, whereas with hydrocortisone it was 2.4 and 2.8 times higher, respectively. In vitro biodegradability of DDAIP was demonstrated in the presence of porcine esterase. The results indicate that DDAIP increases markedly the transepidermal delivery of several types of drug substances.</description><identifier>ISSN: 0724-8741</identifier><identifier>EISSN: 1573-904X</identifier><identifier>DOI: 10.1023/A:1018980905312</identifier><identifier>PMID: 8290477</identifier><identifier>CODEN: PHREEB</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>Administration, Cutaneous ; Alanine - analogs & derivatives ; Alanine - chemical synthesis ; Alanine - pharmacology ; Animals ; Biodegradation, Environmental ; Biological and medical sciences ; Clonidine - administration & dosage ; Colubridae ; General pharmacology ; Hydrocortisone - administration & dosage ; In Vitro Techniques ; Indomethacin - administration & dosage ; Medical sciences ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. 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H</creatorcontrib><title>Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone</title><title>Pharmaceutical research</title><addtitle>Pharm Res</addtitle><description>The biodegradable transdermal penetration enhancer, dodecyl 2-(N,N-dimethylamino)propionate (II; DDAIP), was prepared by reacting dodecyl 2-bromopropionate (I), obtained by reaction of n-dodecanol with 2-bromopropionyl halogenide, with dimethylamine. The penetration enhancing effects of DDAIP on the transport of indomethacin, clonidine, and hydrocortisone across shed snake skin (Elaphe obsoleta) were evaluated. Azone and lauryl alcohol, a possible decomposition product of DDAIP, were used as standard enhancers for comparison. In terms of flux, DDAIP showed 4.7 and 7.5 times the promoting effect for indomethacin compared to azone and lauryl alcohol, respectively. With clonidine this effect was 1.7 and 3.1 times, whereas with hydrocortisone it was 2.4 and 2.8 times higher, respectively. In vitro biodegradability of DDAIP was demonstrated in the presence of porcine esterase. The results indicate that DDAIP increases markedly the transepidermal delivery of several types of drug substances.</description><subject>Administration, Cutaneous</subject><subject>Alanine - analogs & derivatives</subject><subject>Alanine - chemical synthesis</subject><subject>Alanine - pharmacology</subject><subject>Animals</subject><subject>Biodegradation, Environmental</subject><subject>Biological and medical sciences</subject><subject>Clonidine - administration & dosage</subject><subject>Colubridae</subject><subject>General pharmacology</subject><subject>Hydrocortisone - administration & dosage</subject><subject>In Vitro Techniques</subject><subject>Indomethacin - administration & dosage</subject><subject>Medical sciences</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Skin Absorption - drug effects</subject><issn>0724-8741</issn><issn>1573-904X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kEtLxDAUhYMoOj7WroQsXChMNWlTk7gT8QWiCxXcyW1y40TapCRV6C_x79rRwdW9cM75DhxC9jk74aysTi_OOeNKK6ZZXfFyjcx4LatCM_G6TmZMlqJQUvAtsp3zB2NMcS02yaYqJ4eUM_L9NIZhgdlnCsFSDAsIxod3is6hGWh01EaLZmxpWRw9zB8K6zscFmMLnQ_xuE-x9zHAgDQGOpHokCBk7L3F1EFLLbb-C9O4JPlg4zIMU8OcmjYGb33A-W_1YrQpmpgGn2PAXbLhoM24t7o75OX66vnytrh_vLm7vLgvTKn4UDRoFYhGlExyVoEzsqq1bkBwJWvGuQAoEVhjeKPPLJ9eXjtpnLLOiDMw1Q45-OP2n02H9q1PvoM0vq0GmvTDlQ7ZQOvScp78b6ukZlrp6ge4R3hn</recordid><startdate>19931101</startdate><enddate>19931101</enddate><creator>BÜYÜKTIMKIN, S</creator><creator>BÜYÜKTIMKIN, N</creator><creator>RYTTING, J. H</creator><general>Springer</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>19931101</creationdate><title>Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone</title><author>BÜYÜKTIMKIN, S ; BÜYÜKTIMKIN, N ; RYTTING, J. H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-bed8a4b4207103afc73599ba418750114aa2ea0bc1b96d1ea015f7cf8dfc46ac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Administration, Cutaneous</topic><topic>Alanine - analogs & derivatives</topic><topic>Alanine - chemical synthesis</topic><topic>Alanine - pharmacology</topic><topic>Animals</topic><topic>Biodegradation, Environmental</topic><topic>Biological and medical sciences</topic><topic>Clonidine - administration & dosage</topic><topic>Colubridae</topic><topic>General pharmacology</topic><topic>Hydrocortisone - administration & dosage</topic><topic>In Vitro Techniques</topic><topic>Indomethacin - administration & dosage</topic><topic>Medical sciences</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Skin Absorption - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>BÜYÜKTIMKIN, S</creatorcontrib><creatorcontrib>BÜYÜKTIMKIN, N</creatorcontrib><creatorcontrib>RYTTING, J. H</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Pharmaceutical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>BÜYÜKTIMKIN, S</au><au>BÜYÜKTIMKIN, N</au><au>RYTTING, J. H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone</atitle><jtitle>Pharmaceutical research</jtitle><addtitle>Pharm Res</addtitle><date>1993-11-01</date><risdate>1993</risdate><volume>10</volume><issue>11</issue><spage>1632</spage><epage>1637</epage><pages>1632-1637</pages><issn>0724-8741</issn><eissn>1573-904X</eissn><coden>PHREEB</coden><abstract>The biodegradable transdermal penetration enhancer, dodecyl 2-(N,N-dimethylamino)propionate (II; DDAIP), was prepared by reacting dodecyl 2-bromopropionate (I), obtained by reaction of n-dodecanol with 2-bromopropionyl halogenide, with dimethylamine. The penetration enhancing effects of DDAIP on the transport of indomethacin, clonidine, and hydrocortisone across shed snake skin (Elaphe obsoleta) were evaluated. Azone and lauryl alcohol, a possible decomposition product of DDAIP, were used as standard enhancers for comparison. In terms of flux, DDAIP showed 4.7 and 7.5 times the promoting effect for indomethacin compared to azone and lauryl alcohol, respectively. With clonidine this effect was 1.7 and 3.1 times, whereas with hydrocortisone it was 2.4 and 2.8 times higher, respectively. In vitro biodegradability of DDAIP was demonstrated in the presence of porcine esterase. The results indicate that DDAIP increases markedly the transepidermal delivery of several types of drug substances.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>8290477</pmid><doi>10.1023/A:1018980905312</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0724-8741 |
| ispartof | Pharmaceutical research, 1993-11, Vol.10 (11), p.1632-1637 |
| issn | 0724-8741 1573-904X |
| language | eng |
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| source | MEDLINE; SpringerLink Journals |
| subjects | Administration, Cutaneous Alanine - analogs & derivatives Alanine - chemical synthesis Alanine - pharmacology Animals Biodegradation, Environmental Biological and medical sciences Clonidine - administration & dosage Colubridae General pharmacology Hydrocortisone - administration & dosage In Vitro Techniques Indomethacin - administration & dosage Medical sciences Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Skin Absorption - drug effects |
| title | Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone |
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