Conformational polymorphism in bicalutamide
Two crystalline forms (forms I and II) and an amorphous phase of bicalutamide were fully characterized through combined results of differential scanning calorimetry, X-ray powder and single crystal diffraction and Raman spectroscopy. Each polymorph crystallizes with one molecule in the asymmetric un...
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| Veröffentlicht in: | International journal of pharmaceutics 2007-01, Vol.328 (2), p.112-118 |
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| container_end_page | 118 |
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| container_title | International journal of pharmaceutics |
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| creator | Vega, Daniel R. Polla, Griselda Martinez, Andrea Mendioroz, Elsa Reinoso, María |
| description | Two crystalline forms (forms I and II) and an amorphous phase of bicalutamide were fully characterized through combined results of differential scanning calorimetry, X-ray powder and single crystal diffraction and Raman spectroscopy. Each polymorph crystallizes with one molecule in the asymmetric unit and the molecular conformations are quite different between them. The main difference is provided by C12–C11–S8–C5 torsion angle, which assumes a value of −88.3(4)° (−Syn–Clinal) and 72.5(4)° (+Syn–Clinal) in forms I and II, respectively. Consequently, molecules in form I show an open folding and molecules in form II a closed one. The relative stability between forms I and II is presented in an energy versus temperature diagram, where forms I and II are considered as a monotropic system, being form I the more stable one. The amorphous phase was observed very metastable and it converts to form II spontaneously at RT in around a week |
| doi_str_mv | 10.1016/j.ijpharm.2006.08.001 |
| format | Article |
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Each polymorph crystallizes with one molecule in the asymmetric unit and the molecular conformations are quite different between them. The main difference is provided by C12–C11–S8–C5 torsion angle, which assumes a value of −88.3(4)° (−Syn–Clinal) and 72.5(4)° (+Syn–Clinal) in forms I and II, respectively. Consequently, molecules in form I show an open folding and molecules in form II a closed one. The relative stability between forms I and II is presented in an energy versus temperature diagram, where forms I and II are considered as a monotropic system, being form I the more stable one. 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Each polymorph crystallizes with one molecule in the asymmetric unit and the molecular conformations are quite different between them. The main difference is provided by C12–C11–S8–C5 torsion angle, which assumes a value of −88.3(4)° (−Syn–Clinal) and 72.5(4)° (+Syn–Clinal) in forms I and II, respectively. Consequently, molecules in form I show an open folding and molecules in form II a closed one. The relative stability between forms I and II is presented in an energy versus temperature diagram, where forms I and II are considered as a monotropic system, being form I the more stable one. The amorphous phase was observed very metastable and it converts to form II spontaneously at RT in around a week</description><subject>Androgen Antagonists - chemistry</subject><subject>Anilides - chemistry</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Bicalutamide</subject><subject>Biological and medical sciences</subject><subject>Calorimetry, Differential Scanning</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Drug Stability</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Nitriles</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Polymorphism</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Spectrum Analysis, Raman</subject><subject>Stability</subject><subject>Thermal analysis</subject><subject>Tosyl Compounds - chemistry</subject><subject>X-Ray Diffraction</subject><issn>0378-5173</issn><issn>1873-3476</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LxDAQhoMo7rr6E5S96EVaJ02bpCeRxS9Y8KLnkCYpm9I2NWmF_fdm2YJHT3N53ndmHoSuMaQYMH1oUtsMO-m7NAOgKfAUAJ-gJeaMJCRn9BQtgTCeFJiRBboIoYEIZpicowWmJeMc4yW637i-dr6To3W9bNeDa_ed88POhm5t-3VllWynUXZWm0t0Vss2mKt5rtDXy_Pn5i3Zfry-b562iSIlGZMcpCpNBZpKgnPDNCGU8ZrJrMgIY4BlrQvKK5npknOmgdS55JiVuDBcgSErdHfsHbz7nkwYRWeDMm0re-OmICiPNQXNIlgcQeVdCN7UYvC2k34vMIiDJdGI2ZI4WBLARbQUczfzgqnqjP5LzVoicDsDMsT_ay97ZcMfx3PAOWWRezxyJur4scaLoKzpldHWGzUK7ew_p_wCHhyHbQ</recordid><startdate>20070110</startdate><enddate>20070110</enddate><creator>Vega, Daniel R.</creator><creator>Polla, Griselda</creator><creator>Martinez, Andrea</creator><creator>Mendioroz, Elsa</creator><creator>Reinoso, María</creator><general>Elsevier B.V</general><general>Elsevier</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>20070110</creationdate><title>Conformational polymorphism in bicalutamide</title><author>Vega, Daniel R. ; Polla, Griselda ; Martinez, Andrea ; Mendioroz, Elsa ; Reinoso, María</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c393t-40ac9eb0d6a314e7d33678f7a25237701afd568ba2d9887d03f4a817915e8c0e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Androgen Antagonists - chemistry</topic><topic>Anilides - chemistry</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Bicalutamide</topic><topic>Biological and medical sciences</topic><topic>Calorimetry, Differential Scanning</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Drug Stability</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Nitriles</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Polymorphism</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Spectrum Analysis, Raman</topic><topic>Stability</topic><topic>Thermal analysis</topic><topic>Tosyl Compounds - chemistry</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vega, Daniel R.</creatorcontrib><creatorcontrib>Polla, Griselda</creatorcontrib><creatorcontrib>Martinez, Andrea</creatorcontrib><creatorcontrib>Mendioroz, Elsa</creatorcontrib><creatorcontrib>Reinoso, María</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>International journal of pharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vega, Daniel R.</au><au>Polla, Griselda</au><au>Martinez, Andrea</au><au>Mendioroz, Elsa</au><au>Reinoso, María</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conformational polymorphism in bicalutamide</atitle><jtitle>International journal of pharmaceutics</jtitle><addtitle>Int J Pharm</addtitle><date>2007-01-10</date><risdate>2007</risdate><volume>328</volume><issue>2</issue><spage>112</spage><epage>118</epage><pages>112-118</pages><issn>0378-5173</issn><eissn>1873-3476</eissn><coden>IJPHDE</coden><abstract>Two crystalline forms (forms I and II) and an amorphous phase of bicalutamide were fully characterized through combined results of differential scanning calorimetry, X-ray powder and single crystal diffraction and Raman spectroscopy. Each polymorph crystallizes with one molecule in the asymmetric unit and the molecular conformations are quite different between them. The main difference is provided by C12–C11–S8–C5 torsion angle, which assumes a value of −88.3(4)° (−Syn–Clinal) and 72.5(4)° (+Syn–Clinal) in forms I and II, respectively. Consequently, molecules in form I show an open folding and molecules in form II a closed one. The relative stability between forms I and II is presented in an energy versus temperature diagram, where forms I and II are considered as a monotropic system, being form I the more stable one. The amorphous phase was observed very metastable and it converts to form II spontaneously at RT in around a week</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>16978811</pmid><doi>10.1016/j.ijpharm.2006.08.001</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Androgen Antagonists - chemistry Anilides - chemistry Antineoplastic Agents - chemistry Bicalutamide Biological and medical sciences Calorimetry, Differential Scanning Crystal structure Crystallization Drug Stability General pharmacology Medical sciences Molecular Conformation Nitriles Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Polymorphism Spectrophotometry, Ultraviolet Spectrum Analysis, Raman Stability Thermal analysis Tosyl Compounds - chemistry X-Ray Diffraction |
| title | Conformational polymorphism in bicalutamide |
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