Photochemistry and Phototoxicity of Fluocinolone 16,17-Acetonide
Fluocinolone 16,17-acetonide is a corticosteroid used topically to treat various inflammatory skin diseases. Its photoreactivity was studied under UV-A and UV-B light in aqueous buffer in the presence of oxygen. This drug is photolabile under UV-B light and, to a lesser extent, under UV-A light, whi...
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| Veröffentlicht in: | Photochemistry and photobiology 2005-03, Vol.81 (2), p.291-298 |
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| creator | Miolo, Giorgia Caffieri, Sergio Dalzoppo, Daniele Ricci, Andrea Fasani, Elisa Albini, Angelo |
| description | Fluocinolone 16,17-acetonide is a corticosteroid used topically to treat various inflammatory skin diseases. Its photoreactivity was studied under UV-A and UV-B light in aqueous buffer in the presence of oxygen. This drug is photolabile under UV-B light and, to a lesser extent, under UV-A light, which is absorbed far less. In phosphate buffer, approximately 80% of fluocinolone acetonide decomposes after 5 J/cm2 of UV-B irradiation, whereas under 30 J/cm2 of UV-A light approximately only 20% decomposes. Both the drug and its photoproducts have been evaluated through a battery of in vitro studies and found to cause photohemolysis and induce photodamage to proteins (erythrocyte ghosts, bovine serum albumin) and linoleic acid. In addition, one of the photoproducts (the 17-hydroperoxy derivative) is highly toxic in the dark. Therefore, both loss of therapeutic activity and light-induced adverse effects may be expected when patients expose themselves to sunlight after drug administration. A major mechanism for phototoxicity involves radicals forming from drug breakdown, at least under UV-B, although reactive oxygen species may play a role, particularly under UV-A. |
| doi_str_mv | 10.1562/2004-05-25-RA-178.1 |
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Its photoreactivity was studied under UV-A and UV-B light in aqueous buffer in the presence of oxygen. This drug is photolabile under UV-B light and, to a lesser extent, under UV-A light, which is absorbed far less. In phosphate buffer, approximately 80% of fluocinolone acetonide decomposes after 5 J/cm2 of UV-B irradiation, whereas under 30 J/cm2 of UV-A light approximately only 20% decomposes. Both the drug and its photoproducts have been evaluated through a battery of in vitro studies and found to cause photohemolysis and induce photodamage to proteins (erythrocyte ghosts, bovine serum albumin) and linoleic acid. In addition, one of the photoproducts (the 17-hydroperoxy derivative) is highly toxic in the dark. Therefore, both loss of therapeutic activity and light-induced adverse effects may be expected when patients expose themselves to sunlight after drug administration. A major mechanism for phototoxicity involves radicals forming from drug breakdown, at least under UV-B, although reactive oxygen species may play a role, particularly under UV-A.</description><identifier>ISSN: 0031-8655</identifier><identifier>EISSN: 1751-1097</identifier><identifier>DOI: 10.1562/2004-05-25-RA-178.1</identifier><identifier>PMID: 15535735</identifier><identifier>CODEN: PHCBAP</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>Dose-Response Relationship, Radiation ; Fluocinolone Acetonide - chemistry ; Fluocinolone Acetonide - pharmacology ; Fluocinolone Acetonide - radiation effects ; Free Radicals - chemistry ; Free Radicals - radiation effects ; Linoleic Acid - chemistry ; Linoleic Acid - radiation effects ; Molecular Conformation ; Oxygen - chemistry ; Photochemistry ; Research s ; Time Factors ; Ultraviolet Rays ; Water - chemistry</subject><ispartof>Photochemistry and photobiology, 2005-03, Vol.81 (2), p.291-298</ispartof><rights>American Society for Photobiology</rights><rights>Copyright American Society of Photobiology Mar/Apr 2005</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-b397t-91c9fc155408da11bb0fb4426b496d8b515a02bf39e7714aa947746c27255833</citedby><cites>FETCH-LOGICAL-b397t-91c9fc155408da11bb0fb4426b496d8b515a02bf39e7714aa947746c27255833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://bioone.org/doi/pdf/10.1562/2004-05-25-RA-178.1$$EPDF$$P50$$Gbioone$$H</linktopdf><link.rule.ids>314,780,784,26976,27922,27923,52361</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15535735$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miolo, Giorgia</creatorcontrib><creatorcontrib>Caffieri, Sergio</creatorcontrib><creatorcontrib>Dalzoppo, Daniele</creatorcontrib><creatorcontrib>Ricci, Andrea</creatorcontrib><creatorcontrib>Fasani, Elisa</creatorcontrib><creatorcontrib>Albini, Angelo</creatorcontrib><title>Photochemistry and Phototoxicity of Fluocinolone 16,17-Acetonide</title><title>Photochemistry and photobiology</title><addtitle>Photochem Photobiol</addtitle><description>Fluocinolone 16,17-acetonide is a corticosteroid used topically to treat various inflammatory skin diseases. Its photoreactivity was studied under UV-A and UV-B light in aqueous buffer in the presence of oxygen. This drug is photolabile under UV-B light and, to a lesser extent, under UV-A light, which is absorbed far less. In phosphate buffer, approximately 80% of fluocinolone acetonide decomposes after 5 J/cm2 of UV-B irradiation, whereas under 30 J/cm2 of UV-A light approximately only 20% decomposes. Both the drug and its photoproducts have been evaluated through a battery of in vitro studies and found to cause photohemolysis and induce photodamage to proteins (erythrocyte ghosts, bovine serum albumin) and linoleic acid. In addition, one of the photoproducts (the 17-hydroperoxy derivative) is highly toxic in the dark. Therefore, both loss of therapeutic activity and light-induced adverse effects may be expected when patients expose themselves to sunlight after drug administration. A major mechanism for phototoxicity involves radicals forming from drug breakdown, at least under UV-B, although reactive oxygen species may play a role, particularly under UV-A.</description><subject>Dose-Response Relationship, Radiation</subject><subject>Fluocinolone Acetonide - chemistry</subject><subject>Fluocinolone Acetonide - pharmacology</subject><subject>Fluocinolone Acetonide - radiation effects</subject><subject>Free Radicals - chemistry</subject><subject>Free Radicals - radiation effects</subject><subject>Linoleic Acid - chemistry</subject><subject>Linoleic Acid - radiation effects</subject><subject>Molecular Conformation</subject><subject>Oxygen - chemistry</subject><subject>Photochemistry</subject><subject>Research s</subject><subject>Time Factors</subject><subject>Ultraviolet Rays</subject><subject>Water - chemistry</subject><issn>0031-8655</issn><issn>1751-1097</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqNkE1LAzEURYMotlZ_gSCDa1PzkrzJZOdQrAoFpXQfJpkMTWknOh9g_71TW3Dr6sHj3HvhEHILbAqY8kfOmKQMKUe6zCmobApnZAwKgQLT6pyMGRNAsxRxRK7adsMYSK3gkowAUaASOCZPH-vYRbf2u9B2zT4p6jL5fXXxO7jQ7ZNYJfNtH12o4zbWPoH0ARTNne9iHUp_TS6qYtv6m9OdkNX8eTV7pYv3l7dZvqBWaNVRDU5XbtiVLCsLAGtZZaXkqZU6LTOLgAXjthLaKwWyKLRUSqaOK46YCTEh98fazyZ-9b7tzCb2TT0sGi4U51qmaoDEEXJNbNvGV-azCbui2Rtg5uDMHJwZhoajWeZmcGZgSN2dqnu78-Vf5iRpAOAI2BAHA_8q_QHtP3R2</recordid><startdate>20050301</startdate><enddate>20050301</enddate><creator>Miolo, Giorgia</creator><creator>Caffieri, Sergio</creator><creator>Dalzoppo, Daniele</creator><creator>Ricci, Andrea</creator><creator>Fasani, Elisa</creator><creator>Albini, Angelo</creator><general>Blackwell Publishing Ltd</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>3V.</scope><scope>4T-</scope><scope>7RV</scope><scope>7TM</scope><scope>7U7</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AF</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>NAPCQ</scope><scope>P64</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>RC3</scope><scope>S0X</scope></search><sort><creationdate>20050301</creationdate><title>Photochemistry and Phototoxicity of Fluocinolone 16,17-Acetonide</title><author>Miolo, Giorgia ; Caffieri, Sergio ; Dalzoppo, Daniele ; Ricci, Andrea ; Fasani, Elisa ; Albini, Angelo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-b397t-91c9fc155408da11bb0fb4426b496d8b515a02bf39e7714aa947746c27255833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Dose-Response Relationship, Radiation</topic><topic>Fluocinolone Acetonide - chemistry</topic><topic>Fluocinolone Acetonide - pharmacology</topic><topic>Fluocinolone Acetonide - radiation effects</topic><topic>Free Radicals - chemistry</topic><topic>Free Radicals - radiation effects</topic><topic>Linoleic Acid - chemistry</topic><topic>Linoleic Acid - radiation effects</topic><topic>Molecular Conformation</topic><topic>Oxygen - chemistry</topic><topic>Photochemistry</topic><topic>Research s</topic><topic>Time Factors</topic><topic>Ultraviolet Rays</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miolo, Giorgia</creatorcontrib><creatorcontrib>Caffieri, Sergio</creatorcontrib><creatorcontrib>Dalzoppo, Daniele</creatorcontrib><creatorcontrib>Ricci, Andrea</creatorcontrib><creatorcontrib>Fasani, Elisa</creatorcontrib><creatorcontrib>Albini, Angelo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Docstoc</collection><collection>Nursing & Allied Health Database</collection><collection>Nucleic Acids Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>STEM Database</collection><collection>ProQuest Pharma Collection</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>ProQuest Biological Science Collection</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>Nursing & Allied Health Premium</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>Genetics Abstracts</collection><collection>SIRS Editorial</collection><jtitle>Photochemistry and photobiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miolo, Giorgia</au><au>Caffieri, Sergio</au><au>Dalzoppo, Daniele</au><au>Ricci, Andrea</au><au>Fasani, Elisa</au><au>Albini, Angelo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photochemistry and Phototoxicity of Fluocinolone 16,17-Acetonide</atitle><jtitle>Photochemistry and photobiology</jtitle><addtitle>Photochem Photobiol</addtitle><date>2005-03-01</date><risdate>2005</risdate><volume>81</volume><issue>2</issue><spage>291</spage><epage>298</epage><pages>291-298</pages><issn>0031-8655</issn><eissn>1751-1097</eissn><coden>PHCBAP</coden><abstract>Fluocinolone 16,17-acetonide is a corticosteroid used topically to treat various inflammatory skin diseases. Its photoreactivity was studied under UV-A and UV-B light in aqueous buffer in the presence of oxygen. This drug is photolabile under UV-B light and, to a lesser extent, under UV-A light, which is absorbed far less. In phosphate buffer, approximately 80% of fluocinolone acetonide decomposes after 5 J/cm2 of UV-B irradiation, whereas under 30 J/cm2 of UV-A light approximately only 20% decomposes. Both the drug and its photoproducts have been evaluated through a battery of in vitro studies and found to cause photohemolysis and induce photodamage to proteins (erythrocyte ghosts, bovine serum albumin) and linoleic acid. In addition, one of the photoproducts (the 17-hydroperoxy derivative) is highly toxic in the dark. Therefore, both loss of therapeutic activity and light-induced adverse effects may be expected when patients expose themselves to sunlight after drug administration. A major mechanism for phototoxicity involves radicals forming from drug breakdown, at least under UV-B, although reactive oxygen species may play a role, particularly under UV-A.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>15535735</pmid><doi>10.1562/2004-05-25-RA-178.1</doi><tpages>8</tpages></addata></record> |
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| subjects | Dose-Response Relationship, Radiation Fluocinolone Acetonide - chemistry Fluocinolone Acetonide - pharmacology Fluocinolone Acetonide - radiation effects Free Radicals - chemistry Free Radicals - radiation effects Linoleic Acid - chemistry Linoleic Acid - radiation effects Molecular Conformation Oxygen - chemistry Photochemistry Research s Time Factors Ultraviolet Rays Water - chemistry |
| title | Photochemistry and Phototoxicity of Fluocinolone 16,17-Acetonide |
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