Ofloxacin β-Cyclodextrin Complexation
Ofloxacin (OFX) is a fluorquinolone characterized by photochemical instability. With the goal to improve its photostability in aqueous solutions, the complexation of ofloxacin with β-cyclodextrin was investigated. The complexes showed a water solubility enhancement of approximately 2.6 times; nevert...
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| Veröffentlicht in: | Drug development and industrial pharmacy 2001-01, Vol.27 (6), p.533-540 |
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| container_title | Drug development and industrial pharmacy |
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| creator | Koester, L. S. Guterres, S. S. Le Roch, M. Eifler-Lima, V. L. Zuanazzi, J. A. Bassani, V. L. |
| description | Ofloxacin (OFX) is a fluorquinolone characterized by photochemical instability. With the goal to improve its photostability in aqueous solutions, the complexation of ofloxacin with β-cyclodextrin was investigated. The complexes showed a water solubility enhancement of approximately 2.6 times; nevertheless, the photodegradation of ofloxacin was not reduced. The complexes obtained were characterized by thermal and 1H nuclear magnetic resonance (NMR) analysis, which revealed an interaction between ofloxacin and β-cyclodextrin. The last analysis indicated that only partial inclusion of the N-methylpiperazinyl moiety occurred, which can explain the fact that photostabilization was not improved. This partial inclusion phenomenon could be explained also by computer-aided molecular modeling. |
| doi_str_mv | 10.1081/DDC-100105178 |
| format | Article |
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S. ; Guterres, S. S. ; Le Roch, M. ; Eifler-Lima, V. L. ; Zuanazzi, J. A. ; Bassani, V. L.</creator><creatorcontrib>Koester, L. S. ; Guterres, S. S. ; Le Roch, M. ; Eifler-Lima, V. L. ; Zuanazzi, J. A. ; Bassani, V. L.</creatorcontrib><description>Ofloxacin (OFX) is a fluorquinolone characterized by photochemical instability. With the goal to improve its photostability in aqueous solutions, the complexation of ofloxacin with β-cyclodextrin was investigated. The complexes showed a water solubility enhancement of approximately 2.6 times; nevertheless, the photodegradation of ofloxacin was not reduced. The complexes obtained were characterized by thermal and 1H nuclear magnetic resonance (NMR) analysis, which revealed an interaction between ofloxacin and β-cyclodextrin. The last analysis indicated that only partial inclusion of the N-methylpiperazinyl moiety occurred, which can explain the fact that photostabilization was not improved. This partial inclusion phenomenon could be explained also by computer-aided molecular modeling.</description><identifier>ISSN: 0363-9045</identifier><identifier>EISSN: 1520-5762</identifier><identifier>DOI: 10.1081/DDC-100105178</identifier><identifier>PMID: 11548860</identifier><language>eng</language><publisher>Colchester: Informa UK Ltd</publisher><subject>Anti-Infective Agents - chemistry ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; beta-Cyclodextrins ; Biological and medical sciences ; Calorimetry, Differential Scanning ; Chromatography, High Pressure Liquid ; Computer Graphics ; Cyclodextrins - chemistry ; Drug Stability ; General pharmacology ; Inclusion complex ; Kinetics ; Light ; Magnetic Resonance Spectroscopy ; Medical sciences ; Models, Molecular ; Ofloxacin ; Ofloxacin - chemistry ; Ofloxacin photostability ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Solubility ; Ultraviolet Rays ; β-Cyclodextrin</subject><ispartof>Drug development and industrial pharmacy, 2001-01, Vol.27 (6), p.533-540</ispartof><rights>2001 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 2001</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-c17bca979b0e155671644e9fd4b91783c145188ada2a0f197368959af7bfdcb23</citedby><cites>FETCH-LOGICAL-c415t-c17bca979b0e155671644e9fd4b91783c145188ada2a0f197368959af7bfdcb23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1081/DDC-100105178$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1081/DDC-100105178$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,778,782,27907,27908,59628,59734,60417,60523,61202,61237,61383,61418</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1090001$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11548860$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Koester, L. S.</creatorcontrib><creatorcontrib>Guterres, S. S.</creatorcontrib><creatorcontrib>Le Roch, M.</creatorcontrib><creatorcontrib>Eifler-Lima, V. L.</creatorcontrib><creatorcontrib>Zuanazzi, J. A.</creatorcontrib><creatorcontrib>Bassani, V. L.</creatorcontrib><title>Ofloxacin β-Cyclodextrin Complexation</title><title>Drug development and industrial pharmacy</title><addtitle>Drug Dev Ind Pharm</addtitle><description>Ofloxacin (OFX) is a fluorquinolone characterized by photochemical instability. With the goal to improve its photostability in aqueous solutions, the complexation of ofloxacin with β-cyclodextrin was investigated. The complexes showed a water solubility enhancement of approximately 2.6 times; nevertheless, the photodegradation of ofloxacin was not reduced. The complexes obtained were characterized by thermal and 1H nuclear magnetic resonance (NMR) analysis, which revealed an interaction between ofloxacin and β-cyclodextrin. The last analysis indicated that only partial inclusion of the N-methylpiperazinyl moiety occurred, which can explain the fact that photostabilization was not improved. This partial inclusion phenomenon could be explained also by computer-aided molecular modeling.</description><subject>Anti-Infective Agents - chemistry</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>beta-Cyclodextrins</subject><subject>Biological and medical sciences</subject><subject>Calorimetry, Differential Scanning</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Computer Graphics</subject><subject>Cyclodextrins - chemistry</subject><subject>Drug Stability</subject><subject>General pharmacology</subject><subject>Inclusion complex</subject><subject>Kinetics</subject><subject>Light</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Ofloxacin</subject><subject>Ofloxacin - chemistry</subject><subject>Ofloxacin photostability</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Solubility</subject><subject>Ultraviolet Rays</subject><subject>β-Cyclodextrin</subject><issn>0363-9045</issn><issn>1520-5762</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtOwzAQRS0EoqWwZItYIHYGTxLH9hKlvKRK3cA6mji2msqNKycV7W_xIXwTRi2vRVejkc5c3TOEnAO7ASbhdjwuKDAGjIOQB2QIPGGUizw5JEOW5ilVLOMDctJ180glivNjMgDgmZQ5G5LrqXV-jbppLz_eabHRztdm3Ye4F36xdGaNfePbU3Jk0XXmbDdH5PXh_qV4opPp43NxN6E6A95TDaLSqISqmAHOcwF5lhll66xSsV6qIeMgJdaYILOgRJpLxRVaUdlaV0k6InSbq4PvumBsuQzNAsOmBFZ--ZbRt_zxjfzFll-uqoWpf-mdYASudgB2Gp0N2Oqm-5OqWAyLmNxiTWt9WOCbD64ue9w4H75v0n0VxL_TmUHXzzQGU879KrTxXXvKfwIzR4CB</recordid><startdate>20010101</startdate><enddate>20010101</enddate><creator>Koester, L. S.</creator><creator>Guterres, S. S.</creator><creator>Le Roch, M.</creator><creator>Eifler-Lima, V. L.</creator><creator>Zuanazzi, J. A.</creator><creator>Bassani, V. L.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20010101</creationdate><title>Ofloxacin β-Cyclodextrin Complexation</title><author>Koester, L. S. ; Guterres, S. S. ; Le Roch, M. ; Eifler-Lima, V. L. ; Zuanazzi, J. A. ; Bassani, V. L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-c17bca979b0e155671644e9fd4b91783c145188ada2a0f197368959af7bfdcb23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Anti-Infective Agents - chemistry</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>beta-Cyclodextrins</topic><topic>Biological and medical sciences</topic><topic>Calorimetry, Differential Scanning</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Computer Graphics</topic><topic>Cyclodextrins - chemistry</topic><topic>Drug Stability</topic><topic>General pharmacology</topic><topic>Inclusion complex</topic><topic>Kinetics</topic><topic>Light</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Ofloxacin</topic><topic>Ofloxacin - chemistry</topic><topic>Ofloxacin photostability</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Solubility</topic><topic>Ultraviolet Rays</topic><topic>β-Cyclodextrin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koester, L. S.</creatorcontrib><creatorcontrib>Guterres, S. S.</creatorcontrib><creatorcontrib>Le Roch, M.</creatorcontrib><creatorcontrib>Eifler-Lima, V. L.</creatorcontrib><creatorcontrib>Zuanazzi, J. A.</creatorcontrib><creatorcontrib>Bassani, V. L.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Drug development and industrial pharmacy</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koester, L. S.</au><au>Guterres, S. S.</au><au>Le Roch, M.</au><au>Eifler-Lima, V. L.</au><au>Zuanazzi, J. A.</au><au>Bassani, V. L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ofloxacin β-Cyclodextrin Complexation</atitle><jtitle>Drug development and industrial pharmacy</jtitle><addtitle>Drug Dev Ind Pharm</addtitle><date>2001-01-01</date><risdate>2001</risdate><volume>27</volume><issue>6</issue><spage>533</spage><epage>540</epage><pages>533-540</pages><issn>0363-9045</issn><eissn>1520-5762</eissn><abstract>Ofloxacin (OFX) is a fluorquinolone characterized by photochemical instability. With the goal to improve its photostability in aqueous solutions, the complexation of ofloxacin with β-cyclodextrin was investigated. The complexes showed a water solubility enhancement of approximately 2.6 times; nevertheless, the photodegradation of ofloxacin was not reduced. The complexes obtained were characterized by thermal and 1H nuclear magnetic resonance (NMR) analysis, which revealed an interaction between ofloxacin and β-cyclodextrin. The last analysis indicated that only partial inclusion of the N-methylpiperazinyl moiety occurred, which can explain the fact that photostabilization was not improved. This partial inclusion phenomenon could be explained also by computer-aided molecular modeling.</abstract><cop>Colchester</cop><pub>Informa UK Ltd</pub><pmid>11548860</pmid><doi>10.1081/DDC-100105178</doi><tpages>8</tpages></addata></record> |
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| source | MEDLINE; EBSCOhost Business Source Complete; Taylor & Francis; Taylor & Francis Medical Library - CRKN |
| subjects | Anti-Infective Agents - chemistry Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents beta-Cyclodextrins Biological and medical sciences Calorimetry, Differential Scanning Chromatography, High Pressure Liquid Computer Graphics Cyclodextrins - chemistry Drug Stability General pharmacology Inclusion complex Kinetics Light Magnetic Resonance Spectroscopy Medical sciences Models, Molecular Ofloxacin Ofloxacin - chemistry Ofloxacin photostability Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Solubility Ultraviolet Rays β-Cyclodextrin |
| title | Ofloxacin β-Cyclodextrin Complexation |
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