Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents
Ibutilide fumarate, racemic N‐[4‐[4‐(ethyl‐n‐heptylamino)‐1‐hydroxybutyl]phenyl]methanesulfonamide hemifumarate, and artilide, the R‐(+)‐enantiomer of N‐[4‐[4‐(di‐n‐butylalmino)‐1‐hydroxybutyl]‐phenyl]methanesulfonamide hemifumerate, are under clinical investigation as Class III antiarrhythmic agent...
Gespeichert in:
| Veröffentlicht in: | Journal of labelled compounds & radiopharmaceuticals 1994-10, Vol.34 (10), p.929-942 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 942 |
|---|---|
| container_issue | 10 |
| container_start_page | 929 |
| container_title | Journal of labelled compounds & radiopharmaceuticals |
| container_volume | 34 |
| creator | Stolle, Wayne T. Stelzer, Lindsay S. Hester, Jackson B. Perricone, Salvatore C. Hsi, Richard S. P. |
| description | Ibutilide fumarate, racemic N‐[4‐[4‐(ethyl‐n‐heptylamino)‐1‐hydroxybutyl]phenyl]methanesulfonamide hemifumarate, and artilide, the R‐(+)‐enantiomer of N‐[4‐[4‐(di‐n‐butylalmino)‐1‐hydroxybutyl]‐phenyl]methanesulfonamide hemifumerate, are under clinical investigation as Class III antiarrhythmic agents. For conducting drug disposition studies, we synthesized carbon‐14 labeled ibutilide, as well as its two enantiomeric forms. In addition, high specific activity tritium labeled ibutilide was also prepared to facilitate development of a radioimmunoassay and for studying receptor site characteristics of this agent. Results of metabolism studies with [14C]ibutilide led us to prepare tritium labeled artilide, which is more readily accessible than the C‐14 labeled drug. The optical antipode of artilide was also labeled with tritium for comparative drug disposition investigations on the two enantiomers. |
| doi_str_mv | 10.1002/jlcr.2580341006 |
| format | Article |
| fullrecord | <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_jlcr_2580341006</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_67QR84G6_G</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3586-ab9e169e93e95a846a0336bc6b7e2b86a916c0355777ac79762e7ea3651c6bda3</originalsourceid><addsrcrecordid>eNqFkL1PwzAQxS0EEqUws2ZgDbVjx07EhCpIQRWIAmK0Ls6FuqRJZUeC_PekDSpiYrqP93530iPknNFLRmk0WVXGXUZxQrnoZ3lARoymaci4EIdkRLmMQtGLx-TE-xWlvSbEiMyeu7pdorc-aMrAQWGbCnKssOgHg2trAqiLAGuoW9us0e0WrQXnll273OnvWLf-lByVUHk8-6lj8np78zKdhfPH7G56PQ8NjxMZQp4ikymmHNMYEiGBci5zI3OFUZ5ISJk0lMexUgqMSpWMUCFwGbPeUwAfk8lw17jGe4el3ji7BtdpRvU2CL0NQv8G0RMXA7EBb6AqHdTG-j0mIq6YSnrb1WD7tBV2_13V9_Pp4s-TcKCtb_FrT4P70FJxFeu3h6zvnhaJyKTO-De-XX9B</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents</title><source>Wiley Online Library</source><creator>Stolle, Wayne T. ; Stelzer, Lindsay S. ; Hester, Jackson B. ; Perricone, Salvatore C. ; Hsi, Richard S. P.</creator><creatorcontrib>Stolle, Wayne T. ; Stelzer, Lindsay S. ; Hester, Jackson B. ; Perricone, Salvatore C. ; Hsi, Richard S. P.</creatorcontrib><description>Ibutilide fumarate, racemic N‐[4‐[4‐(ethyl‐n‐heptylamino)‐1‐hydroxybutyl]phenyl]methanesulfonamide hemifumarate, and artilide, the R‐(+)‐enantiomer of N‐[4‐[4‐(di‐n‐butylalmino)‐1‐hydroxybutyl]‐phenyl]methanesulfonamide hemifumerate, are under clinical investigation as Class III antiarrhythmic agents. For conducting drug disposition studies, we synthesized carbon‐14 labeled ibutilide, as well as its two enantiomeric forms. In addition, high specific activity tritium labeled ibutilide was also prepared to facilitate development of a radioimmunoassay and for studying receptor site characteristics of this agent. Results of metabolism studies with [14C]ibutilide led us to prepare tritium labeled artilide, which is more readily accessible than the C‐14 labeled drug. The optical antipode of artilide was also labeled with tritium for comparative drug disposition investigations on the two enantiomers.</description><identifier>ISSN: 0362-4803</identifier><identifier>EISSN: 1099-1344</identifier><identifier>DOI: 10.1002/jlcr.2580341006</identifier><language>eng</language><publisher>Chichester: John Wiley & Sons, Ltd</publisher><subject>Antiarrhythmics ; Artilide ; Carbon-14 ; Chemistry ; Enantiomers ; Exact sciences and technology ; Ibutilide ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Tritium</subject><ispartof>Journal of labelled compounds & radiopharmaceuticals, 1994-10, Vol.34 (10), p.929-942</ispartof><rights>Copyright © 1994 John Wiley & Sons, Ltd.</rights><rights>1994 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3586-ab9e169e93e95a846a0336bc6b7e2b86a916c0355777ac79762e7ea3651c6bda3</citedby><cites>FETCH-LOGICAL-c3586-ab9e169e93e95a846a0336bc6b7e2b86a916c0355777ac79762e7ea3651c6bda3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlcr.2580341006$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlcr.2580341006$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4237178$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Stolle, Wayne T.</creatorcontrib><creatorcontrib>Stelzer, Lindsay S.</creatorcontrib><creatorcontrib>Hester, Jackson B.</creatorcontrib><creatorcontrib>Perricone, Salvatore C.</creatorcontrib><creatorcontrib>Hsi, Richard S. P.</creatorcontrib><title>Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents</title><title>Journal of labelled compounds & radiopharmaceuticals</title><addtitle>J Label Compd Radiopharm</addtitle><description>Ibutilide fumarate, racemic N‐[4‐[4‐(ethyl‐n‐heptylamino)‐1‐hydroxybutyl]phenyl]methanesulfonamide hemifumarate, and artilide, the R‐(+)‐enantiomer of N‐[4‐[4‐(di‐n‐butylalmino)‐1‐hydroxybutyl]‐phenyl]methanesulfonamide hemifumerate, are under clinical investigation as Class III antiarrhythmic agents. For conducting drug disposition studies, we synthesized carbon‐14 labeled ibutilide, as well as its two enantiomeric forms. In addition, high specific activity tritium labeled ibutilide was also prepared to facilitate development of a radioimmunoassay and for studying receptor site characteristics of this agent. Results of metabolism studies with [14C]ibutilide led us to prepare tritium labeled artilide, which is more readily accessible than the C‐14 labeled drug. The optical antipode of artilide was also labeled with tritium for comparative drug disposition investigations on the two enantiomers.</description><subject>Antiarrhythmics</subject><subject>Artilide</subject><subject>Carbon-14</subject><subject>Chemistry</subject><subject>Enantiomers</subject><subject>Exact sciences and technology</subject><subject>Ibutilide</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Tritium</subject><issn>0362-4803</issn><issn>1099-1344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxS0EEqUws2ZgDbVjx07EhCpIQRWIAmK0Ls6FuqRJZUeC_PekDSpiYrqP93530iPknNFLRmk0WVXGXUZxQrnoZ3lARoymaci4EIdkRLmMQtGLx-TE-xWlvSbEiMyeu7pdorc-aMrAQWGbCnKssOgHg2trAqiLAGuoW9us0e0WrQXnll273OnvWLf-lByVUHk8-6lj8np78zKdhfPH7G56PQ8NjxMZQp4ikymmHNMYEiGBci5zI3OFUZ5ISJk0lMexUgqMSpWMUCFwGbPeUwAfk8lw17jGe4el3ji7BtdpRvU2CL0NQv8G0RMXA7EBb6AqHdTG-j0mIq6YSnrb1WD7tBV2_13V9_Pp4s-TcKCtb_FrT4P70FJxFeu3h6zvnhaJyKTO-De-XX9B</recordid><startdate>199410</startdate><enddate>199410</enddate><creator>Stolle, Wayne T.</creator><creator>Stelzer, Lindsay S.</creator><creator>Hester, Jackson B.</creator><creator>Perricone, Salvatore C.</creator><creator>Hsi, Richard S. P.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199410</creationdate><title>Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents</title><author>Stolle, Wayne T. ; Stelzer, Lindsay S. ; Hester, Jackson B. ; Perricone, Salvatore C. ; Hsi, Richard S. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3586-ab9e169e93e95a846a0336bc6b7e2b86a916c0355777ac79762e7ea3651c6bda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Antiarrhythmics</topic><topic>Artilide</topic><topic>Carbon-14</topic><topic>Chemistry</topic><topic>Enantiomers</topic><topic>Exact sciences and technology</topic><topic>Ibutilide</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Tritium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stolle, Wayne T.</creatorcontrib><creatorcontrib>Stelzer, Lindsay S.</creatorcontrib><creatorcontrib>Hester, Jackson B.</creatorcontrib><creatorcontrib>Perricone, Salvatore C.</creatorcontrib><creatorcontrib>Hsi, Richard S. P.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stolle, Wayne T.</au><au>Stelzer, Lindsay S.</au><au>Hester, Jackson B.</au><au>Perricone, Salvatore C.</au><au>Hsi, Richard S. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents</atitle><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle><addtitle>J Label Compd Radiopharm</addtitle><date>1994-10</date><risdate>1994</risdate><volume>34</volume><issue>10</issue><spage>929</spage><epage>942</epage><pages>929-942</pages><issn>0362-4803</issn><eissn>1099-1344</eissn><abstract>Ibutilide fumarate, racemic N‐[4‐[4‐(ethyl‐n‐heptylamino)‐1‐hydroxybutyl]phenyl]methanesulfonamide hemifumarate, and artilide, the R‐(+)‐enantiomer of N‐[4‐[4‐(di‐n‐butylalmino)‐1‐hydroxybutyl]‐phenyl]methanesulfonamide hemifumerate, are under clinical investigation as Class III antiarrhythmic agents. For conducting drug disposition studies, we synthesized carbon‐14 labeled ibutilide, as well as its two enantiomeric forms. In addition, high specific activity tritium labeled ibutilide was also prepared to facilitate development of a radioimmunoassay and for studying receptor site characteristics of this agent. Results of metabolism studies with [14C]ibutilide led us to prepare tritium labeled artilide, which is more readily accessible than the C‐14 labeled drug. The optical antipode of artilide was also labeled with tritium for comparative drug disposition investigations on the two enantiomers.</abstract><cop>Chichester</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/jlcr.2580341006</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0362-4803 |
| ispartof | Journal of labelled compounds & radiopharmaceuticals, 1994-10, Vol.34 (10), p.929-942 |
| issn | 0362-4803 1099-1344 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_jlcr_2580341006 |
| source | Wiley Online Library |
| subjects | Antiarrhythmics Artilide Carbon-14 Chemistry Enantiomers Exact sciences and technology Ibutilide Noncondensed benzenic compounds Organic chemistry Preparations and properties Tritium |
| title | Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T19%3A17%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20radiolabeled%20racemic%20and%20enantiomeric%20antiarrhythmic%20agents&rft.jtitle=Journal%20of%20labelled%20compounds%20&%20radiopharmaceuticals&rft.au=Stolle,%20Wayne%20T.&rft.date=1994-10&rft.volume=34&rft.issue=10&rft.spage=929&rft.epage=942&rft.pages=929-942&rft.issn=0362-4803&rft.eissn=1099-1344&rft_id=info:doi/10.1002/jlcr.2580341006&rft_dat=%3Cistex_cross%3Eark_67375_WNG_67QR84G6_G%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |