Solubility and Some Crystallization Properties of Conglomerate Forming Chiral Drug Guaifenesin in Water
The solubility of 3-(2-methoxyphenoxy)-propane-1,2-diol, the well-known chiral drug guaifenesin 1, in water has been investigated by means of polythermal and isothermal approaches. It was found that the solubilities of racemic and enantiomeric diols rac- and (R)-1 depend strongly on temperature. The...
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| Veröffentlicht in: | Journal of pharmaceutical sciences 2014-10, Vol.103 (10), p.3176-3182 |
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| creator | Fayzullin, Robert R. Lorenz, Heike Bredikhina, Zemfira A. Bredikhin, Alexander A. Seidel-Morgenstern, Andreas |
| description | The solubility of 3-(2-methoxyphenoxy)-propane-1,2-diol, the well-known chiral drug guaifenesin 1, in water has been investigated by means of polythermal and isothermal approaches. It was found that the solubilities of racemic and enantiomeric diols rac- and (R)-1 depend strongly on temperature. The ternary phase diagram of the guaifenesin enantiomers in water in the temperature range between 10°C and 40°C was constructed. Clear evidence was obtained that rac-1 crystallizes as a stable conglomerate. The Meyerhoffer coefficient for the guaifenesin–water system is more than two and strongly depends on temperature. Neither crystalline hydrates nor polymorphs were detected within the range of conditions covered. Metastable zone width data with regard to primary nucleation were also collected for rac-1 and (R)-1. On the basis of the knowledge acquired, the resolution of racemic guaifenesin by preferential crystallization from solution could be realized successfully. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 103:3176–3182, 2014 |
| doi_str_mv | 10.1002/jps.24104 |
| format | Article |
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It was found that the solubilities of racemic and enantiomeric diols rac- and (R)-1 depend strongly on temperature. The ternary phase diagram of the guaifenesin enantiomers in water in the temperature range between 10°C and 40°C was constructed. Clear evidence was obtained that rac-1 crystallizes as a stable conglomerate. The Meyerhoffer coefficient for the guaifenesin–water system is more than two and strongly depends on temperature. Neither crystalline hydrates nor polymorphs were detected within the range of conditions covered. Metastable zone width data with regard to primary nucleation were also collected for rac-1 and (R)-1. On the basis of the knowledge acquired, the resolution of racemic guaifenesin by preferential crystallization from solution could be realized successfully. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 103:3176–3182, 2014</description><identifier>ISSN: 0022-3549</identifier><identifier>EISSN: 1520-6017</identifier><identifier>DOI: 10.1002/jps.24104</identifier><identifier>PMID: 25091705</identifier><identifier>CODEN: JPMSAE</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>chirality ; Crystallization ; Expectorants - chemistry ; guaifenesin ; Guaifenesin - chemistry ; metastable zone width ; miscibility gap ; phase diagram ; Powder Diffraction ; preferential crystallization ; racemic conglomerate ; separation science ; Solubility ; Stereoisomerism ; Water - chemistry ; X-ray powder diffractometry</subject><ispartof>Journal of pharmaceutical sciences, 2014-10, Vol.103 (10), p.3176-3182</ispartof><rights>2014 Wiley Periodicals, Inc. and the American Pharmacists Association</rights><rights>2014 Wiley Periodicals, Inc. and the American Pharmacists Association.</rights><rights>Copyright © 2014 Wiley Periodicals, Inc., A Wiley Company</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4674-1657d9453f7abc6bbc42fba23bd786f78105495c2c136c55efcff28ca9afd5013</citedby><cites>FETCH-LOGICAL-c4674-1657d9453f7abc6bbc42fba23bd786f78105495c2c136c55efcff28ca9afd5013</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%2Fjps.24104$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjps.24104$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25091705$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fayzullin, Robert R.</creatorcontrib><creatorcontrib>Lorenz, Heike</creatorcontrib><creatorcontrib>Bredikhina, Zemfira A.</creatorcontrib><creatorcontrib>Bredikhin, Alexander A.</creatorcontrib><creatorcontrib>Seidel-Morgenstern, Andreas</creatorcontrib><title>Solubility and Some Crystallization Properties of Conglomerate Forming Chiral Drug Guaifenesin in Water</title><title>Journal of pharmaceutical sciences</title><addtitle>J Pharm Sci</addtitle><description>The solubility of 3-(2-methoxyphenoxy)-propane-1,2-diol, the well-known chiral drug guaifenesin 1, in water has been investigated by means of polythermal and isothermal approaches. It was found that the solubilities of racemic and enantiomeric diols rac- and (R)-1 depend strongly on temperature. The ternary phase diagram of the guaifenesin enantiomers in water in the temperature range between 10°C and 40°C was constructed. Clear evidence was obtained that rac-1 crystallizes as a stable conglomerate. The Meyerhoffer coefficient for the guaifenesin–water system is more than two and strongly depends on temperature. Neither crystalline hydrates nor polymorphs were detected within the range of conditions covered. Metastable zone width data with regard to primary nucleation were also collected for rac-1 and (R)-1. On the basis of the knowledge acquired, the resolution of racemic guaifenesin by preferential crystallization from solution could be realized successfully. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 103:3176–3182, 2014</description><subject>chirality</subject><subject>Crystallization</subject><subject>Expectorants - chemistry</subject><subject>guaifenesin</subject><subject>Guaifenesin - chemistry</subject><subject>metastable zone width</subject><subject>miscibility gap</subject><subject>phase diagram</subject><subject>Powder Diffraction</subject><subject>preferential crystallization</subject><subject>racemic conglomerate</subject><subject>separation science</subject><subject>Solubility</subject><subject>Stereoisomerism</subject><subject>Water - chemistry</subject><subject>X-ray powder diffractometry</subject><issn>0022-3549</issn><issn>1520-6017</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10EFrFDEUB_Agil2rB7-ABLzYw7QvmUlm9yhTW5WChVU8hkzmZc2SSdZkRtl-erNu60EUAjnklz_v_Ql5yeCcAfCL7S6f84ZB84gsmOBQSWDtY7Iob7yqRbM6Ic9y3gKABCGekhMuYMVaEAuyWUc_9867aU91GOg6jki7tM-T9t7d6cnFQG9T3GGaHGYaLe1i2PjCkp6QXsU0urCh3TeXtKeXad7Q61k7iwGzC7Scr8Wl5-SJ1T7ji_v7lHy5eve5e1_dfLr-0L29qUwj26ZiUrTDqhG1bXVvZN-bhtte87of2qW07ZJBWUcYblgtjRBojbV8afRK20EAq0_Jm2PuLsXvM-ZJjS4b9F4HjHNWTEjJGEgBhb7-i27jnEKZ7qAaYLLhB3V2VCbFnBNatUtu1GmvGKhD-6q0r363X-yr-8S5H3H4Ix_qLuDiCH46j_v_J6mPt-uHyPr4A0tpPxwmlY3DYHBwCc2khuj-Mcgv6j2gZw</recordid><startdate>201410</startdate><enddate>201410</enddate><creator>Fayzullin, Robert R.</creator><creator>Lorenz, Heike</creator><creator>Bredikhina, Zemfira A.</creator><creator>Bredikhin, Alexander A.</creator><creator>Seidel-Morgenstern, Andreas</creator><general>Elsevier Inc</general><general>Elsevier Limited</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>7QO</scope><scope>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>201410</creationdate><title>Solubility and Some Crystallization Properties of Conglomerate Forming Chiral Drug Guaifenesin in Water</title><author>Fayzullin, Robert R. ; 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| subjects | chirality Crystallization Expectorants - chemistry guaifenesin Guaifenesin - chemistry metastable zone width miscibility gap phase diagram Powder Diffraction preferential crystallization racemic conglomerate separation science Solubility Stereoisomerism Water - chemistry X-ray powder diffractometry |
| title | Solubility and Some Crystallization Properties of Conglomerate Forming Chiral Drug Guaifenesin in Water |
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