Direct chiral separation of troglitazone stereoisomers using reversed-phase high-performance liquid chromatography
A simple HPLC method for the direct chiral separation of troglitazone stereoisomers was developed. The separation was performed on a reversed-phase cellulose-derivertized chiral column (Chiralcel OJ-R) using a mobile phase consisting of methanol–acetic acid (1000:1, v/v) at a flow rate of 0.5 ml/min...
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| Veröffentlicht in: | Journal of pharmaceutical and biomedical analysis 2002-10, Vol.30 (3), p.823-836 |
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| container_title | Journal of pharmaceutical and biomedical analysis |
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| creator | Suzuki, Nobuyuki Takemura, Akira Miyamoto, Akifumi Yoshioka, Takao Tsutsumi, Shinya Kawasaki, Takao |
| description | A simple HPLC method for the direct chiral separation of troglitazone stereoisomers was developed. The separation was performed on a reversed-phase cellulose-derivertized chiral column (Chiralcel OJ-R) using a mobile phase consisting of methanol–acetic acid (1000:1, v/v) at a flow rate of 0.5 ml/min. The peak areas of stereoisomers separated from 0.13 to 0.75 mg/ml of troglitazone had good linearity, with correlation coefficients >0.999 in the reversed-phase mode. The repeatability of the ratios of stereoisomers isolated from 0.5 mg/ml of troglitazone had a relative standard deviation of 0.1–0.2%. The relative sensitivities of the four isomers at UV 285 nm were similar, as each response factor was within the range of 0.99–1.01. Troglitazone racemized at the chiral center of the thiazolidine ring in methanol solution, but was found to be stable for 24 h in methanol–acetic acid (1000:1, v/v). This method was applied to the stereoisomeric analysis of troglitazone in pharmaceutical formulations and used to evaluate the constancy of the stereoisomer ratio in the manufacturing process and stability testing. |
| doi_str_mv | 10.1016/S0731-7085(02)00391-6 |
| format | Article |
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The separation was performed on a reversed-phase cellulose-derivertized chiral column (Chiralcel OJ-R) using a mobile phase consisting of methanol–acetic acid (1000:1, v/v) at a flow rate of 0.5 ml/min. The peak areas of stereoisomers separated from 0.13 to 0.75 mg/ml of troglitazone had good linearity, with correlation coefficients >0.999 in the reversed-phase mode. The repeatability of the ratios of stereoisomers isolated from 0.5 mg/ml of troglitazone had a relative standard deviation of 0.1–0.2%. The relative sensitivities of the four isomers at UV 285 nm were similar, as each response factor was within the range of 0.99–1.01. Troglitazone racemized at the chiral center of the thiazolidine ring in methanol solution, but was found to be stable for 24 h in methanol–acetic acid (1000:1, v/v). This method was applied to the stereoisomeric analysis of troglitazone in pharmaceutical formulations and used to evaluate the constancy of the stereoisomer ratio in the manufacturing process and stability testing.</description><identifier>ISSN: 0731-7085</identifier><identifier>EISSN: 1873-264X</identifier><identifier>DOI: 10.1016/S0731-7085(02)00391-6</identifier><identifier>PMID: 12367708</identifier><identifier>CODEN: JPBADA</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Analysis ; Anti-diabetic drug ; Biological and medical sciences ; Chemistry, Pharmaceutical ; Chiral column ; Chiral separation ; Chromans - analysis ; Chromans - chemistry ; Chromatography, High Pressure Liquid - methods ; General pharmacology ; Medical sciences ; Pharmacology. Drug treatments ; Reproducibility of Results ; Reversed-phase LC ; Stereoisomerism ; Thiazoles - analysis ; Thiazoles - chemistry ; Thiazolidinediones ; Troglitazone</subject><ispartof>Journal of pharmaceutical and biomedical analysis, 2002-10, Vol.30 (3), p.823-836</ispartof><rights>2002 Elsevier Science B.V.</rights><rights>2003 INIST-CNRS</rights><rights>Copyright 2002 Elsevier Science B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-f67b41f1d8e0fc12bcfb6dd2c247da881a9f467cd447a1917e2a54af48e4e5eb3</citedby><cites>FETCH-LOGICAL-c391t-f67b41f1d8e0fc12bcfb6dd2c247da881a9f467cd447a1917e2a54af48e4e5eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0731708502003916$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>309,310,314,776,780,785,786,3537,23909,23910,25118,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13983518$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12367708$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Suzuki, Nobuyuki</creatorcontrib><creatorcontrib>Takemura, Akira</creatorcontrib><creatorcontrib>Miyamoto, Akifumi</creatorcontrib><creatorcontrib>Yoshioka, Takao</creatorcontrib><creatorcontrib>Tsutsumi, Shinya</creatorcontrib><creatorcontrib>Kawasaki, Takao</creatorcontrib><title>Direct chiral separation of troglitazone stereoisomers using reversed-phase high-performance liquid chromatography</title><title>Journal of pharmaceutical and biomedical analysis</title><addtitle>J Pharm Biomed Anal</addtitle><description>A simple HPLC method for the direct chiral separation of troglitazone stereoisomers was developed. The separation was performed on a reversed-phase cellulose-derivertized chiral column (Chiralcel OJ-R) using a mobile phase consisting of methanol–acetic acid (1000:1, v/v) at a flow rate of 0.5 ml/min. The peak areas of stereoisomers separated from 0.13 to 0.75 mg/ml of troglitazone had good linearity, with correlation coefficients >0.999 in the reversed-phase mode. The repeatability of the ratios of stereoisomers isolated from 0.5 mg/ml of troglitazone had a relative standard deviation of 0.1–0.2%. The relative sensitivities of the four isomers at UV 285 nm were similar, as each response factor was within the range of 0.99–1.01. Troglitazone racemized at the chiral center of the thiazolidine ring in methanol solution, but was found to be stable for 24 h in methanol–acetic acid (1000:1, v/v). This method was applied to the stereoisomeric analysis of troglitazone in pharmaceutical formulations and used to evaluate the constancy of the stereoisomer ratio in the manufacturing process and stability testing.</description><subject>Analysis</subject><subject>Anti-diabetic drug</subject><subject>Biological and medical sciences</subject><subject>Chemistry, Pharmaceutical</subject><subject>Chiral column</subject><subject>Chiral separation</subject><subject>Chromans - analysis</subject><subject>Chromans - chemistry</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Reproducibility of Results</subject><subject>Reversed-phase LC</subject><subject>Stereoisomerism</subject><subject>Thiazoles - analysis</subject><subject>Thiazoles - chemistry</subject><subject>Thiazolidinediones</subject><subject>Troglitazone</subject><issn>0731-7085</issn><issn>1873-264X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1u1TAQRi0EoreFRwBlA4JFwHYcO1lVqJRSqRILQGJnOfb4xiiJ03FSqX16fH9El12NrDnzeXxMyBtGPzHK5OefVFWsVLSpP1D-kdKqZaV8RjasUVXJpfjznGz-IyfkNKW_lNKateIlOWG8kio3NgS_BgS7FLYPaIYiwWzQLCFORfTFgnE7hMU8xAmKtABCDCmOgKlYU5i2BcJdPoAr594kKPqw7csZ0EcczWShGMLtGlwOxziaJW7RzP39K_LCmyHB62M9I7-_Xf66-F7e_Li6vvhyU9r8lqX0UnWCeeYaoN4y3lnfSee45UI50zTMtF5IZZ0QyrCWKeCmFsaLBgTU0FVn5P0hd8Z4u0Ja9BiShWEwE8Q1acVZLau6zWB9AC3GlBC8njGMBu81o3onW-9l651JTbney9Yyz709XrB2I7jHqaPdDLw7AiZZM3jMUkJ65Kq2qWq2484PHGQddwFQJxsgC3T7z9EuhidW-Qf095-0</recordid><startdate>20021015</startdate><enddate>20021015</enddate><creator>Suzuki, Nobuyuki</creator><creator>Takemura, Akira</creator><creator>Miyamoto, Akifumi</creator><creator>Yoshioka, Takao</creator><creator>Tsutsumi, Shinya</creator><creator>Kawasaki, Takao</creator><general>Elsevier B.V</general><general>Elsevier Science</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><scope>7X8</scope></search><sort><creationdate>20021015</creationdate><title>Direct chiral separation of troglitazone stereoisomers using reversed-phase high-performance liquid chromatography</title><author>Suzuki, Nobuyuki ; Takemura, Akira ; Miyamoto, Akifumi ; Yoshioka, Takao ; Tsutsumi, Shinya ; Kawasaki, Takao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-f67b41f1d8e0fc12bcfb6dd2c247da881a9f467cd447a1917e2a54af48e4e5eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Analysis</topic><topic>Anti-diabetic drug</topic><topic>Biological and medical sciences</topic><topic>Chemistry, Pharmaceutical</topic><topic>Chiral column</topic><topic>Chiral separation</topic><topic>Chromans - analysis</topic><topic>Chromans - chemistry</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Reproducibility of Results</topic><topic>Reversed-phase LC</topic><topic>Stereoisomerism</topic><topic>Thiazoles - analysis</topic><topic>Thiazoles - chemistry</topic><topic>Thiazolidinediones</topic><topic>Troglitazone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suzuki, Nobuyuki</creatorcontrib><creatorcontrib>Takemura, Akira</creatorcontrib><creatorcontrib>Miyamoto, Akifumi</creatorcontrib><creatorcontrib>Yoshioka, Takao</creatorcontrib><creatorcontrib>Tsutsumi, Shinya</creatorcontrib><creatorcontrib>Kawasaki, Takao</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><collection>MEDLINE - Academic</collection><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suzuki, Nobuyuki</au><au>Takemura, Akira</au><au>Miyamoto, Akifumi</au><au>Yoshioka, Takao</au><au>Tsutsumi, Shinya</au><au>Kawasaki, Takao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct chiral separation of troglitazone stereoisomers using reversed-phase high-performance liquid chromatography</atitle><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle><addtitle>J Pharm Biomed Anal</addtitle><date>2002-10-15</date><risdate>2002</risdate><volume>30</volume><issue>3</issue><spage>823</spage><epage>836</epage><pages>823-836</pages><issn>0731-7085</issn><eissn>1873-264X</eissn><coden>JPBADA</coden><abstract>A simple HPLC method for the direct chiral separation of troglitazone stereoisomers was developed. The separation was performed on a reversed-phase cellulose-derivertized chiral column (Chiralcel OJ-R) using a mobile phase consisting of methanol–acetic acid (1000:1, v/v) at a flow rate of 0.5 ml/min. The peak areas of stereoisomers separated from 0.13 to 0.75 mg/ml of troglitazone had good linearity, with correlation coefficients >0.999 in the reversed-phase mode. The repeatability of the ratios of stereoisomers isolated from 0.5 mg/ml of troglitazone had a relative standard deviation of 0.1–0.2%. The relative sensitivities of the four isomers at UV 285 nm were similar, as each response factor was within the range of 0.99–1.01. Troglitazone racemized at the chiral center of the thiazolidine ring in methanol solution, but was found to be stable for 24 h in methanol–acetic acid (1000:1, v/v). This method was applied to the stereoisomeric analysis of troglitazone in pharmaceutical formulations and used to evaluate the constancy of the stereoisomer ratio in the manufacturing process and stability testing.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>12367708</pmid><doi>10.1016/S0731-7085(02)00391-6</doi><tpages>14</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Analysis Anti-diabetic drug Biological and medical sciences Chemistry, Pharmaceutical Chiral column Chiral separation Chromans - analysis Chromans - chemistry Chromatography, High Pressure Liquid - methods General pharmacology Medical sciences Pharmacology. Drug treatments Reproducibility of Results Reversed-phase LC Stereoisomerism Thiazoles - analysis Thiazoles - chemistry Thiazolidinediones Troglitazone |
| title | Direct chiral separation of troglitazone stereoisomers using reversed-phase high-performance liquid chromatography |
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