NDLI: Salt Stability – The Effect of pH$_{max}$ on Salt to Free Base Conversion

Content Provider	Springer Nature Link
Author	Hsieh, Yi Ling Merritt, Jeremy M. Yu, Weili Taylor, Lynne S.
Copyright Year	2015
Abstract	The aim of this study was to investigate how the disproportionation process can be impacted by the properties of the salt, specifically pH$_{max}$.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.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.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.
Starting Page	3110
Ending Page	3118
Page Count	9
File Format	PDF
ISSN	07248741
Journal	Pharmaceutical Research
Volume Number	32
Issue Number	9
e-ISSN	1573904X
Language	English
Publisher	Springer US
Publisher Date	2015-04-15
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Pharmacology/Toxicology Pharmacy Biochemistry Medical Law Biomedical Engineering
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology Molecular Medicine Pharmacology (medical) Biotechnology Pharmaceutical Science

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