Salt Stability – The Effect of pHmax on Salt to Free Base Conversion
Purpose The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH max . Methods Five miconazole salts and four sertraline salts were selected for this study. The extent of conversion was quantified using Raman spectrosc...
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| Veröffentlicht in: | Pharmaceutical research 2015-09, Vol.32 (9), p.3110-3118 |
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| creator | Hsieh, Yi-Ling Merritt, Jeremy M. Yu, Weili Taylor, Lynne S. |
| description | Purpose
The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH
max
.
Methods
Five miconazole salts and four sertraline salts were selected for this study. The extent of conversion was quantified using Raman spectroscopy. A mathematical model was utilized to estimate the theoretical amount of conversion.
Results
A trend was observed that for a given series of salts of a particular basic compound (both sertraline and miconazole are bases), the extent of disproportionation increases as pH
max
decreases. Miconazole phosphate monohydrate and sertraline mesylate, although exhibiting significantly different pH
max
values (more than 2 units apart), underwent a similar extent of disproportionation, which may be attributed to the lower buffering capacity of sertraline salts.
Conclusion
This work shows that the disproportionation tendency can be influenced by pH
max
and buffering capacity and thus highlights the importance of selecting the appropriate salt form during the screening process in order to avoid salt-to-free form conversion. |
| doi_str_mv | 10.1007/s11095-015-1691-5 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1702649833</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1702649833</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2595-4d682cdc881de55ab7c38324a7ca5acf665344c10a51b026b507b1dda3d6ae593</originalsourceid><addsrcrecordid>eNp9kLFOwzAURS0EoqXwASzII0vAL7bjZISqpUiVGFokNstxHEiVxMVOEd34B_6QL8ElhZHpSX7nXj0fhM6BXAEh4toDkIxHBHgESQYRP0BD4IJGGWFPh2hIRMyiVDAYoBPvV4SQFDJ2jAYxD6-csiGaLlTd4UWn8qquui3--vjEyxeDJ2VpdIdtidezRr1j2-IfsrN46ozBt8obPLbtm3G-su0pOipV7c3Zfo7Q43SyHM-i-cPd_fhmHumYh0tZkaSxLnSaQmE4V7nQNKUxU0IrrnSZJOEopoEoDjmJk5wTkUNRKFokyvCMjtBl37t29nVjfCebymtT16o1duMliJBiWUppQKFHtbPeO1PKtasa5bYSiNzpk70-GfTJnT7JQ-ZiX7_JG1P8JX59BSDuAR9W7bNxcmU3rg1f_qf1Gz_meZU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1702649833</pqid></control><display><type>article</type><title>Salt Stability – The Effect of pHmax on Salt to Free Base Conversion</title><source>MEDLINE</source><source>SpringerLink Journals - AutoHoldings</source><creator>Hsieh, Yi-Ling ; Merritt, Jeremy M. ; Yu, Weili ; Taylor, Lynne S.</creator><creatorcontrib>Hsieh, Yi-Ling ; Merritt, Jeremy M. ; Yu, Weili ; Taylor, Lynne S.</creatorcontrib><description>Purpose
The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH
max
.
Methods
Five miconazole salts and four sertraline salts were selected for this study. The extent of conversion was quantified using Raman spectroscopy. A mathematical model was utilized to estimate the theoretical amount of conversion.
Results
A trend was observed that for a given series of salts of a particular basic compound (both sertraline and miconazole are bases), the extent of disproportionation increases as pH
max
decreases. Miconazole phosphate monohydrate and sertraline mesylate, although exhibiting significantly different pH
max
values (more than 2 units apart), underwent a similar extent of disproportionation, which may be attributed to the lower buffering capacity of sertraline salts.
Conclusion
This work shows that the disproportionation tendency can be influenced by pH
max
and buffering capacity and thus highlights the importance of selecting the appropriate salt form during the screening process in order to avoid salt-to-free form conversion.</description><identifier>ISSN: 0724-8741</identifier><identifier>EISSN: 1573-904X</identifier><identifier>DOI: 10.1007/s11095-015-1691-5</identifier><identifier>PMID: 25874534</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkalies - chemistry ; Biochemistry ; Biomedical and Life Sciences ; Biomedical Engineering and Bioengineering ; Biomedicine ; Drug Stability ; Hydrogen-Ion Concentration ; Medical Law ; Mesylates - chemistry ; Miconazole - chemistry ; Pharmacology/Toxicology ; Pharmacy ; Research Paper ; Salts - chemistry ; Sertraline - chemistry ; Spectrum Analysis, Raman - methods</subject><ispartof>Pharmaceutical research, 2015-09, Vol.32 (9), p.3110-3118</ispartof><rights>Springer Science+Business Media New York 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2595-4d682cdc881de55ab7c38324a7ca5acf665344c10a51b026b507b1dda3d6ae593</citedby><cites>FETCH-LOGICAL-c2595-4d682cdc881de55ab7c38324a7ca5acf665344c10a51b026b507b1dda3d6ae593</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11095-015-1691-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11095-015-1691-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,41469,42538,51300</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25874534$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hsieh, Yi-Ling</creatorcontrib><creatorcontrib>Merritt, Jeremy M.</creatorcontrib><creatorcontrib>Yu, Weili</creatorcontrib><creatorcontrib>Taylor, Lynne S.</creatorcontrib><title>Salt Stability – The Effect of pHmax on Salt to Free Base Conversion</title><title>Pharmaceutical research</title><addtitle>Pharm Res</addtitle><addtitle>Pharm Res</addtitle><description>Purpose
The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH
max
.
Methods
Five miconazole salts and four sertraline salts were selected for this study. The extent of conversion was quantified using Raman spectroscopy. A mathematical model was utilized to estimate the theoretical amount of conversion.
Results
A trend was observed that for a given series of salts of a particular basic compound (both sertraline and miconazole are bases), the extent of disproportionation increases as pH
max
decreases. Miconazole phosphate monohydrate and sertraline mesylate, although exhibiting significantly different pH
max
values (more than 2 units apart), underwent a similar extent of disproportionation, which may be attributed to the lower buffering capacity of sertraline salts.
Conclusion
This work shows that the disproportionation tendency can be influenced by pH
max
and buffering capacity and thus highlights the importance of selecting the appropriate salt form during the screening process in order to avoid salt-to-free form conversion.</description><subject>Alkalies - chemistry</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedical Engineering and Bioengineering</subject><subject>Biomedicine</subject><subject>Drug Stability</subject><subject>Hydrogen-Ion Concentration</subject><subject>Medical Law</subject><subject>Mesylates - chemistry</subject><subject>Miconazole - chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Research Paper</subject><subject>Salts - chemistry</subject><subject>Sertraline - chemistry</subject><subject>Spectrum Analysis, Raman - methods</subject><issn>0724-8741</issn><issn>1573-904X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kLFOwzAURS0EoqXwASzII0vAL7bjZISqpUiVGFokNstxHEiVxMVOEd34B_6QL8ElhZHpSX7nXj0fhM6BXAEh4toDkIxHBHgESQYRP0BD4IJGGWFPh2hIRMyiVDAYoBPvV4SQFDJ2jAYxD6-csiGaLlTd4UWn8qquui3--vjEyxeDJ2VpdIdtidezRr1j2-IfsrN46ozBt8obPLbtm3G-su0pOipV7c3Zfo7Q43SyHM-i-cPd_fhmHumYh0tZkaSxLnSaQmE4V7nQNKUxU0IrrnSZJOEopoEoDjmJk5wTkUNRKFokyvCMjtBl37t29nVjfCebymtT16o1duMliJBiWUppQKFHtbPeO1PKtasa5bYSiNzpk70-GfTJnT7JQ-ZiX7_JG1P8JX59BSDuAR9W7bNxcmU3rg1f_qf1Gz_meZU</recordid><startdate>201509</startdate><enddate>201509</enddate><creator>Hsieh, Yi-Ling</creator><creator>Merritt, Jeremy M.</creator><creator>Yu, Weili</creator><creator>Taylor, Lynne S.</creator><general>Springer US</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>7X8</scope></search><sort><creationdate>201509</creationdate><title>Salt Stability – The Effect of pHmax on Salt to Free Base Conversion</title><author>Hsieh, Yi-Ling ; Merritt, Jeremy M. ; Yu, Weili ; Taylor, Lynne S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2595-4d682cdc881de55ab7c38324a7ca5acf665344c10a51b026b507b1dda3d6ae593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkalies - chemistry</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedical Engineering and Bioengineering</topic><topic>Biomedicine</topic><topic>Drug Stability</topic><topic>Hydrogen-Ion Concentration</topic><topic>Medical Law</topic><topic>Mesylates - chemistry</topic><topic>Miconazole - chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Research Paper</topic><topic>Salts - chemistry</topic><topic>Sertraline - chemistry</topic><topic>Spectrum Analysis, Raman - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hsieh, Yi-Ling</creatorcontrib><creatorcontrib>Merritt, Jeremy M.</creatorcontrib><creatorcontrib>Yu, Weili</creatorcontrib><creatorcontrib>Taylor, Lynne S.</creatorcontrib><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>Pharmaceutical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hsieh, Yi-Ling</au><au>Merritt, Jeremy M.</au><au>Yu, Weili</au><au>Taylor, Lynne S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Salt Stability – The Effect of pHmax on Salt to Free Base Conversion</atitle><jtitle>Pharmaceutical research</jtitle><stitle>Pharm Res</stitle><addtitle>Pharm Res</addtitle><date>2015-09</date><risdate>2015</risdate><volume>32</volume><issue>9</issue><spage>3110</spage><epage>3118</epage><pages>3110-3118</pages><issn>0724-8741</issn><eissn>1573-904X</eissn><abstract>Purpose
The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH
max
.
Methods
Five miconazole salts and four sertraline salts were selected for this study. The extent of conversion was quantified using Raman spectroscopy. A mathematical model was utilized to estimate the theoretical amount of conversion.
Results
A trend was observed that for a given series of salts of a particular basic compound (both sertraline and miconazole are bases), the extent of disproportionation increases as pH
max
decreases. Miconazole phosphate monohydrate and sertraline mesylate, although exhibiting significantly different pH
max
values (more than 2 units apart), underwent a similar extent of disproportionation, which may be attributed to the lower buffering capacity of sertraline salts.
Conclusion
This work shows that the disproportionation tendency can be influenced by pH
max
and buffering capacity and thus highlights the importance of selecting the appropriate salt form during the screening process in order to avoid salt-to-free form conversion.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>25874534</pmid><doi>10.1007/s11095-015-1691-5</doi><tpages>9</tpages></addata></record> |
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| subjects | Alkalies - chemistry Biochemistry Biomedical and Life Sciences Biomedical Engineering and Bioengineering Biomedicine Drug Stability Hydrogen-Ion Concentration Medical Law Mesylates - chemistry Miconazole - chemistry Pharmacology/Toxicology Pharmacy Research Paper Salts - chemistry Sertraline - chemistry Spectrum Analysis, Raman - methods |
| title | Salt Stability – The Effect of pHmax on Salt to Free Base Conversion |
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