Abstract
The partitioning of two non-steroidal anti-inflammatory drugs (NSAIDs), flurbiprofen and ketoprofen, into cationic cetyltrimethylammonium micelles was investigated using semi-equilibrium dialysis at 37℃ in phosphate buffered saline. The micellar-water solubilization equilibrium constants for both NSAIDs, in their deprotonated forms, were observed to decrease linearly with increasing mole fraction of drug in micelles. For flurbiprofen, the solubilization constant in the limit as mole fraction of drug in micelles approaches zero was found to be 11,200 (co = 1 M), while for ketoprofen the value was 1950 (co = 1 M). Using 1H-NMR and UV spectroscopic techniques, the locus of solubilization for ketoprofen was found to be towards the charged exterior of the micelles, in the Stern layer, whereas flurbiprofen was found to solubilize more in the micellar interior.
Highlights
Non-steroidal anti-inflammatory drugs (NSAIDs) are a classification of medication used primarily for their anti-inflammatory, antipyretic, and analgesic activities
non-steroidal anti-inflammatory drugs (NSAIDs),mic Across similar micellar mole fraction ranges, this trend has been observed for cresols with cetylpyridinium chloride (CPC) [35], for benzoate with CPC [36], and for phenol with CPC [37]
Semi-equilibrium dialysis was used to assess the partitioning of flurbiprofen and ketoprofen into cetyltrimethylammonium bromide (CTAB) micelles
Summary
Non-steroidal anti-inflammatory drugs (NSAIDs) are a classification of medication used primarily for their anti-inflammatory, antipyretic, and analgesic activities. Certain NSAIDs have emerged as valuable drugs in the treatment or prevention of breast cancer [2], colorectal cancer [3], bone loss in postmenopausal women [4], and even certain neurodegenerative diseases [5]. Surfactant micelles have been shown to improve these biopharmaceutical properties when used as drug carriers [7], few studies have investigated the physico-chemical interactions between NSAIDs and surfactants, especially as a function of micellar mole fraction of drug Such studies are of interest to both the pharmaceutical sciences, because of micellar-based drug delivery systems and the use of surfactant systems as biological membrane mimics, and to the environmental sciences, because of the impact these drugs have on both terrestrial and marine ecosystems, and their potential removal using a surfactant-based remediation technology i.e. micellar-enhanced ultrafiltration (MEUF)
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