Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules
Tetralysal® is a Galderma oral drug product (DP) marketed for the treatment of acne. Tetralysal® is sold in capsules containing either 150 mg or 300 mg of the drug substance. In the British Pharmacopoeia monograph for Lymecycline Capsules, the impurities already specified in the drug substance (A-G)...
Gespeichert in:
| Veröffentlicht in: | European journal of pharmaceutical sciences 2023-09, Vol.188, p.106519-106519, Article 106519 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 106519 |
|---|---|
| container_issue | |
| container_start_page | 106519 |
| container_title | European journal of pharmaceutical sciences |
| container_volume | 188 |
| creator | Billié, Stéphan Reversé, Kevin Arlabosse, Jean-Marie Bertin, Didier Boulier, Antoine Cachot, Tony Chambon, Sandrine Charras, Karine Cren, Cécile Furnes, Bjarte Gerfaud, Thibaud Joly-Battaglini, Marine Longoni, Davide Mouis, Gregoire Pierre, Romain Raynard, Héloïse Texier, Thomas Trognon, Caroline Zanelli, Ugo Boiteau, Jean-Guy Harris, Craig S. |
| description | Tetralysal® is a Galderma oral drug product (DP) marketed for the treatment of acne. Tetralysal® is sold in capsules containing either 150 mg or 300 mg of the drug substance. In the British Pharmacopoeia monograph for Lymecycline Capsules, the impurities already specified in the drug substance (A-G), visible in the European Pharmacopoeia 〈1654〉, are also specified together with an unidentified impurity at RRT 1.6 (Impurity J). Based on both monographs Galderma has focused on characterizing most of specified and unspecified impurities to better understand the stability and degradation processes of the formulation. In this manuscript, through both formal synthesis, preparative LCMS and formal degradation studies, we are the first group to confirm the structural identities of 5 unidentified impurities (Impurity J (RRT 1.6), RRT 2.2, 2.4, 2.6 and 3.4), conditions which exacerbate the formation of all 5 impurities and response factors for RRT 2.2, 2.6 and 3.4.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejps.2023.106519 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2841027393</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0928098723001495</els_id><sourcerecordid>2841027393</sourcerecordid><originalsourceid>FETCH-LOGICAL-c351t-f6172aad9256baeaf97aee57eede5341542047d0f1c7e6b4395119c20c90f0403</originalsourceid><addsrcrecordid>eNp9kM9q3DAQh0Vo6G7TvkAOQcceYmf0x5YFuZSlaRMWCiG99CK08hi08cqOZKfsS-Uh8mSx2W2PuczA8P1-MB8h5wxyBqy82ua47VPOgYvpUBZMn5Alq5TOQHH4QJageZWBrtSCfEppCwBlpeAjWQglVVVUYkn-3NYYBt94ZwffBdo1dAyPofsbqN_1Y_SDx0TvLun9_QPlOb-chpxHSW2oqcgl9YEOOETb7pNtX1-os30aW0yfyWlj24RfjvuM_L75_rD6ma1__bhdfVtnThRsyJqSKW5trXlRbizaRiuLWCjEGgshWSE5SFVDw5zCciOFLhjTjoPT0IAEcUa-Hnr72D2NmAaz88lh29qA3ZgMryQDroQWE8oPqItdShEb00e_s3FvGJjZqdma2amZnZqD0yl0cewfNzus_0f-SZyA6wOA05fPHqNJzmNwWPuIbjB159_rfwMFOIVc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2841027393</pqid></control><display><type>article</type><title>Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules</title><source>DOAJ Directory of Open Access Journals</source><source>Elsevier ScienceDirect Journals</source><source>EZB-FREE-00999 freely available EZB journals</source><creator>Billié, Stéphan ; Reversé, Kevin ; Arlabosse, Jean-Marie ; Bertin, Didier ; Boulier, Antoine ; Cachot, Tony ; Chambon, Sandrine ; Charras, Karine ; Cren, Cécile ; Furnes, Bjarte ; Gerfaud, Thibaud ; Joly-Battaglini, Marine ; Longoni, Davide ; Mouis, Gregoire ; Pierre, Romain ; Raynard, Héloïse ; Texier, Thomas ; Trognon, Caroline ; Zanelli, Ugo ; Boiteau, Jean-Guy ; Harris, Craig S.</creator><creatorcontrib>Billié, Stéphan ; Reversé, Kevin ; Arlabosse, Jean-Marie ; Bertin, Didier ; Boulier, Antoine ; Cachot, Tony ; Chambon, Sandrine ; Charras, Karine ; Cren, Cécile ; Furnes, Bjarte ; Gerfaud, Thibaud ; Joly-Battaglini, Marine ; Longoni, Davide ; Mouis, Gregoire ; Pierre, Romain ; Raynard, Héloïse ; Texier, Thomas ; Trognon, Caroline ; Zanelli, Ugo ; Boiteau, Jean-Guy ; Harris, Craig S.</creatorcontrib><description>Tetralysal® is a Galderma oral drug product (DP) marketed for the treatment of acne. Tetralysal® is sold in capsules containing either 150 mg or 300 mg of the drug substance. In the British Pharmacopoeia monograph for Lymecycline Capsules, the impurities already specified in the drug substance (A-G), visible in the European Pharmacopoeia 〈1654〉, are also specified together with an unidentified impurity at RRT 1.6 (Impurity J). Based on both monographs Galderma has focused on characterizing most of specified and unspecified impurities to better understand the stability and degradation processes of the formulation. In this manuscript, through both formal synthesis, preparative LCMS and formal degradation studies, we are the first group to confirm the structural identities of 5 unidentified impurities (Impurity J (RRT 1.6), RRT 2.2, 2.4, 2.6 and 3.4), conditions which exacerbate the formation of all 5 impurities and response factors for RRT 2.2, 2.6 and 3.4.
[Display omitted]</description><identifier>ISSN: 0928-0987</identifier><identifier>EISSN: 1879-0720</identifier><identifier>DOI: 10.1016/j.ejps.2023.106519</identifier><identifier>PMID: 37478583</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>12-aminotetracycline ; Allotetracycline ; Retro-Claisen ; Tetralysal</subject><ispartof>European journal of pharmaceutical sciences, 2023-09, Vol.188, p.106519-106519, Article 106519</ispartof><rights>2023 The Author(s)</rights><rights>Copyright © 2023 The Author(s). Published by Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c351t-f6172aad9256baeaf97aee57eede5341542047d0f1c7e6b4395119c20c90f0403</cites><orcidid>0000-0002-1136-8236</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0928098723001495$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,860,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37478583$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Billié, Stéphan</creatorcontrib><creatorcontrib>Reversé, Kevin</creatorcontrib><creatorcontrib>Arlabosse, Jean-Marie</creatorcontrib><creatorcontrib>Bertin, Didier</creatorcontrib><creatorcontrib>Boulier, Antoine</creatorcontrib><creatorcontrib>Cachot, Tony</creatorcontrib><creatorcontrib>Chambon, Sandrine</creatorcontrib><creatorcontrib>Charras, Karine</creatorcontrib><creatorcontrib>Cren, Cécile</creatorcontrib><creatorcontrib>Furnes, Bjarte</creatorcontrib><creatorcontrib>Gerfaud, Thibaud</creatorcontrib><creatorcontrib>Joly-Battaglini, Marine</creatorcontrib><creatorcontrib>Longoni, Davide</creatorcontrib><creatorcontrib>Mouis, Gregoire</creatorcontrib><creatorcontrib>Pierre, Romain</creatorcontrib><creatorcontrib>Raynard, Héloïse</creatorcontrib><creatorcontrib>Texier, Thomas</creatorcontrib><creatorcontrib>Trognon, Caroline</creatorcontrib><creatorcontrib>Zanelli, Ugo</creatorcontrib><creatorcontrib>Boiteau, Jean-Guy</creatorcontrib><creatorcontrib>Harris, Craig S.</creatorcontrib><title>Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules</title><title>European journal of pharmaceutical sciences</title><addtitle>Eur J Pharm Sci</addtitle><description>Tetralysal® is a Galderma oral drug product (DP) marketed for the treatment of acne. Tetralysal® is sold in capsules containing either 150 mg or 300 mg of the drug substance. In the British Pharmacopoeia monograph for Lymecycline Capsules, the impurities already specified in the drug substance (A-G), visible in the European Pharmacopoeia 〈1654〉, are also specified together with an unidentified impurity at RRT 1.6 (Impurity J). Based on both monographs Galderma has focused on characterizing most of specified and unspecified impurities to better understand the stability and degradation processes of the formulation. In this manuscript, through both formal synthesis, preparative LCMS and formal degradation studies, we are the first group to confirm the structural identities of 5 unidentified impurities (Impurity J (RRT 1.6), RRT 2.2, 2.4, 2.6 and 3.4), conditions which exacerbate the formation of all 5 impurities and response factors for RRT 2.2, 2.6 and 3.4.
[Display omitted]</description><subject>12-aminotetracycline</subject><subject>Allotetracycline</subject><subject>Retro-Claisen</subject><subject>Tetralysal</subject><issn>0928-0987</issn><issn>1879-0720</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kM9q3DAQh0Vo6G7TvkAOQcceYmf0x5YFuZSlaRMWCiG99CK08hi08cqOZKfsS-Uh8mSx2W2PuczA8P1-MB8h5wxyBqy82ua47VPOgYvpUBZMn5Alq5TOQHH4QJageZWBrtSCfEppCwBlpeAjWQglVVVUYkn-3NYYBt94ZwffBdo1dAyPofsbqN_1Y_SDx0TvLun9_QPlOb-chpxHSW2oqcgl9YEOOETb7pNtX1-os30aW0yfyWlj24RfjvuM_L75_rD6ma1__bhdfVtnThRsyJqSKW5trXlRbizaRiuLWCjEGgshWSE5SFVDw5zCciOFLhjTjoPT0IAEcUa-Hnr72D2NmAaz88lh29qA3ZgMryQDroQWE8oPqItdShEb00e_s3FvGJjZqdma2amZnZqD0yl0cewfNzus_0f-SZyA6wOA05fPHqNJzmNwWPuIbjB159_rfwMFOIVc</recordid><startdate>20230901</startdate><enddate>20230901</enddate><creator>Billié, Stéphan</creator><creator>Reversé, Kevin</creator><creator>Arlabosse, Jean-Marie</creator><creator>Bertin, Didier</creator><creator>Boulier, Antoine</creator><creator>Cachot, Tony</creator><creator>Chambon, Sandrine</creator><creator>Charras, Karine</creator><creator>Cren, Cécile</creator><creator>Furnes, Bjarte</creator><creator>Gerfaud, Thibaud</creator><creator>Joly-Battaglini, Marine</creator><creator>Longoni, Davide</creator><creator>Mouis, Gregoire</creator><creator>Pierre, Romain</creator><creator>Raynard, Héloïse</creator><creator>Texier, Thomas</creator><creator>Trognon, Caroline</creator><creator>Zanelli, Ugo</creator><creator>Boiteau, Jean-Guy</creator><creator>Harris, Craig S.</creator><general>Elsevier B.V</general><scope>6I.</scope><scope>AAFTH</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1136-8236</orcidid></search><sort><creationdate>20230901</creationdate><title>Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules</title><author>Billié, Stéphan ; Reversé, Kevin ; Arlabosse, Jean-Marie ; Bertin, Didier ; Boulier, Antoine ; Cachot, Tony ; Chambon, Sandrine ; Charras, Karine ; Cren, Cécile ; Furnes, Bjarte ; Gerfaud, Thibaud ; Joly-Battaglini, Marine ; Longoni, Davide ; Mouis, Gregoire ; Pierre, Romain ; Raynard, Héloïse ; Texier, Thomas ; Trognon, Caroline ; Zanelli, Ugo ; Boiteau, Jean-Guy ; Harris, Craig S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-f6172aad9256baeaf97aee57eede5341542047d0f1c7e6b4395119c20c90f0403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>12-aminotetracycline</topic><topic>Allotetracycline</topic><topic>Retro-Claisen</topic><topic>Tetralysal</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Billié, Stéphan</creatorcontrib><creatorcontrib>Reversé, Kevin</creatorcontrib><creatorcontrib>Arlabosse, Jean-Marie</creatorcontrib><creatorcontrib>Bertin, Didier</creatorcontrib><creatorcontrib>Boulier, Antoine</creatorcontrib><creatorcontrib>Cachot, Tony</creatorcontrib><creatorcontrib>Chambon, Sandrine</creatorcontrib><creatorcontrib>Charras, Karine</creatorcontrib><creatorcontrib>Cren, Cécile</creatorcontrib><creatorcontrib>Furnes, Bjarte</creatorcontrib><creatorcontrib>Gerfaud, Thibaud</creatorcontrib><creatorcontrib>Joly-Battaglini, Marine</creatorcontrib><creatorcontrib>Longoni, Davide</creatorcontrib><creatorcontrib>Mouis, Gregoire</creatorcontrib><creatorcontrib>Pierre, Romain</creatorcontrib><creatorcontrib>Raynard, Héloïse</creatorcontrib><creatorcontrib>Texier, Thomas</creatorcontrib><creatorcontrib>Trognon, Caroline</creatorcontrib><creatorcontrib>Zanelli, Ugo</creatorcontrib><creatorcontrib>Boiteau, Jean-Guy</creatorcontrib><creatorcontrib>Harris, Craig S.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Billié, Stéphan</au><au>Reversé, Kevin</au><au>Arlabosse, Jean-Marie</au><au>Bertin, Didier</au><au>Boulier, Antoine</au><au>Cachot, Tony</au><au>Chambon, Sandrine</au><au>Charras, Karine</au><au>Cren, Cécile</au><au>Furnes, Bjarte</au><au>Gerfaud, Thibaud</au><au>Joly-Battaglini, Marine</au><au>Longoni, Davide</au><au>Mouis, Gregoire</au><au>Pierre, Romain</au><au>Raynard, Héloïse</au><au>Texier, Thomas</au><au>Trognon, Caroline</au><au>Zanelli, Ugo</au><au>Boiteau, Jean-Guy</au><au>Harris, Craig S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules</atitle><jtitle>European journal of pharmaceutical sciences</jtitle><addtitle>Eur J Pharm Sci</addtitle><date>2023-09-01</date><risdate>2023</risdate><volume>188</volume><spage>106519</spage><epage>106519</epage><pages>106519-106519</pages><artnum>106519</artnum><issn>0928-0987</issn><eissn>1879-0720</eissn><abstract>Tetralysal® is a Galderma oral drug product (DP) marketed for the treatment of acne. Tetralysal® is sold in capsules containing either 150 mg or 300 mg of the drug substance. In the British Pharmacopoeia monograph for Lymecycline Capsules, the impurities already specified in the drug substance (A-G), visible in the European Pharmacopoeia 〈1654〉, are also specified together with an unidentified impurity at RRT 1.6 (Impurity J). Based on both monographs Galderma has focused on characterizing most of specified and unspecified impurities to better understand the stability and degradation processes of the formulation. In this manuscript, through both formal synthesis, preparative LCMS and formal degradation studies, we are the first group to confirm the structural identities of 5 unidentified impurities (Impurity J (RRT 1.6), RRT 2.2, 2.4, 2.6 and 3.4), conditions which exacerbate the formation of all 5 impurities and response factors for RRT 2.2, 2.6 and 3.4.
[Display omitted]</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>37478583</pmid><doi>10.1016/j.ejps.2023.106519</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-1136-8236</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0928-0987 |
| ispartof | European journal of pharmaceutical sciences, 2023-09, Vol.188, p.106519-106519, Article 106519 |
| issn | 0928-0987 1879-0720 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2841027393 |
| source | DOAJ Directory of Open Access Journals; Elsevier ScienceDirect Journals; EZB-FREE-00999 freely available EZB journals |
| subjects | 12-aminotetracycline Allotetracycline Retro-Claisen Tetralysal |
| title | Identification of unknown impurities J, RRT 2.2, 2.4, 2.6 and 3.4 in tetralysal® capsules |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T09%3A25%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Identification%20of%20unknown%20impurities%20J,%20RRT%202.2,%202.4,%202.6%20and%203.4%20in%20tetralysal%C2%AE%20capsules&rft.jtitle=European%20journal%20of%20pharmaceutical%20sciences&rft.au=Billi%C3%A9,%20St%C3%A9phan&rft.date=2023-09-01&rft.volume=188&rft.spage=106519&rft.epage=106519&rft.pages=106519-106519&rft.artnum=106519&rft.issn=0928-0987&rft.eissn=1879-0720&rft_id=info:doi/10.1016/j.ejps.2023.106519&rft_dat=%3Cproquest_cross%3E2841027393%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2841027393&rft_id=info:pmid/37478583&rft_els_id=S0928098723001495&rfr_iscdi=true |