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Coffman, Renee; Kildsig, Dane O.

doi:10.1023/a:1016011125302

Cited by 76 publications

(58 citation statements)

References 14 publications

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“…Another example, nicotinamide, is well-known to self-associate in water so the temptation persists. 22 However, urea has no significant tendency to self-associate in water, so for urea at least, the analogy cannot be correct. 23 As we shall see, the analogy is positively wrong.…”

Section: Jonathan J Boothmentioning

confidence: 99%

Practical molecular thermodynamics for greener solution chemistry

2017

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We all know that to enhance solubility using greener chemistry we should harness sound principles of molecular-based thermodynamics. The problem is that even for simple systems it can be hard to know how to use fundamental tools for formulation benefit, and for the more complex systems that we must often use, calculations required for molecular thermodynamics can often be quite involved. In this paper we show that a fundamental, assumption-free statistical thermodynamics approach, the Kirkwood-Buff theory, can be used in practical, complex aqueous systems to provide the insights we need to optimise formulations. The theory itself is not that difficult, but its implementation, which requires many steps of thermodynamic calculations, has up to now not been straightforward. Taking full advantage of an interactive approach, here we review what the Kirkwood-Buff theory can provide for formulators; we use the power of modern web browsers to provide open-source, user-friendly, responsive-design apps to do the hard work of data analysis, leaving formulators to focus on the interpretation of the results for their specific optimisation task. Indeed the apps are intended to be used by researchers and formulators for specific systems of interest to them.

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Section: Jonathan J Boothmentioning

confidence: 99%

Practical molecular thermodynamics for greener solution chemistry

2017

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“…The following hypothesis was formulated [225]. CAF and NMD molecules are well known as effective hydrotropes increasing the solubility of aromatic drugs via the hetero-association mechanism [163,[194][195][196]. However, their hydrotropic potency is limited due to their intrinsic ability to self-associate.…”

Section: Hetero-association In Three-component Systemsmentioning

confidence: 99%

Hetero-association of aromatic molecules in aqueous solution

Evstigneev

2014

International Reviews in Physical Chemistry

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Knowledge of the physical chemistry of small molecules complexation (the hetero-association) in aqueous solution is increasingly important in view of the rapidly emerging branch of supramolecular chemistry dealing with the formation of heterogeneous polymeric structures having specific functional roles. In this paper, the 50-year history of scientific studies of hetero-association of heterocyclic aromatic molecules in aqueous solution has been reviewed. Some important correlations of structural and thermodynamic parameters of complexation have been reported based on large data-set of hetero-association parameters accumulated to date. The fundamental problem of 'energetic composition' of π-stacking is extensively discussed. The review has shown that there are some gaps in our understanding of heteroassociation, which provides a challenge for further studies in this area.

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“…The complexation of some local anesthetic esters such as benzocaine, 2) procaine, 3) and lidocaine 4) (LDC) with caffeine was also attempted to inhibit the hydrolysis of the ester group on these drugs in aqueous solution. To improve chemical stability and/or increase solubility, such molecular coupling, which is not covalent bonding, has been extensively investigated, for example, riboflavin-nicotinamide, 5) ampicillin-benzaldehyde, 6) and iodine-polyvinyl pyrrolidone. 7) Indomethacin (IDM), a non-steroidal anti-inflammatory drug (NSAID), has been widely used to treat tendovaginitis, arthritis, and muscle pain as an ointment, cream, gel and adhesive plaster.…”

mentioning

confidence: 99%

Molecular Complex Consisting of Two Typical External Medicines: Intermolecular Interaction between Indomethacin and Lidocaine

Umeda

Fukami

Furuishi

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Molecular complexes have been studied to improve the physico-chemical properties of drugs for the past half century. Higuchi et al. reported that caffeine formed complexes with benzoic acid and various benzoate derivative esters in solution.1) They attempted the first quantitative evaluation regarding the molecular association responsible for the existence of these complexes and the effect on chemical stability. The complexation of some local anesthetic esters such as benzocaine,2) procaine, 3) and lidocaine 4) (LDC) with caffeine was also attempted to inhibit the hydrolysis of the ester group on these drugs in aqueous solution. To improve chemical stability and/or increase solubility, such molecular coupling, which is not covalent bonding, has been extensively investigated, for example, riboflavin-nicotinamide, 5) ampicillin-benzaldehyde, 6) and iodine-polyvinyl pyrrolidone. 7)Indomethacin (IDM), a non-steroidal anti-inflammatory drug (NSAID), has been widely used to treat tendovaginitis, arthritis, and muscle pain as an ointment, cream, gel and adhesive plaster. Since IDM is, however, practically insoluble (ca. 2.5 mg/ml) in water, cyclodextrins, 8,9) poly(amidoamine) dendrimers, 10) and several additives 11) have been utilized to improve its dissolution. Furthermore, skin permeation of IDM was enhanced by the complexation of additives with L-menthol 12) or smectite. 13)LDC topical systems are used to relieve the pain and discomfort associated with herpes zoster virus infections of the skin. Our previous study using Neurometer ® demonstrated that the application of a 9% LDC ointment decreased sensory nerve function in 12 volunteers. Nevertheless, pain relief was not achieved efficiently, because the hydrochloride salt of LDC did not sufficiently penetrate the skin tissue.14) Accordingly, the LDC ointment was reformulated by adding IDM which was expected to heal the inflamed region, because there is no commercially available external medicine consisting of LDC and IDM. In a preliminary study, we obtained a reconstituted viscous paste from IDM and LDC kneaded with an appropriate amount of water.In this study, the intermolecular interaction between IDM and LDC was examined and the formation of a complex was confirmed using thermal analysis, a polarized microscope with a hot stage, fast-atom bombardment (FAB)-MS, phasesolubility techniques, IR, and 1 H-NMR. Finally, the molecular structure of the novel complex in aqueous solution was estimated. ExperimentalMaterials IDM and LDC were of reagent grade and purchased from Wako Pure Chemical Industries Ltd. (Osaka, Japan). All other chemicals and solvents were of reagent grade and used without further purification.Preparation of the IDM and LDC Complex An equimolar mixture of IDM and LDC was kneaded with an appropriate amount of distilled water using an agate mortar and pestle for 20 min. Then the milled mixture was dried at room temperature under reduced pressure overnight.Determination of IDM and LDC IDM, LDC, and the kneaded mixture were subjected to a HPLC analysis...

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Untitled

Cited by 76 publications

References 14 publications

Practical molecular thermodynamics for greener solution chemistry

Practical molecular thermodynamics for greener solution chemistry

Hetero-association of aromatic molecules in aqueous solution

Molecular Complex Consisting of Two Typical External Medicines: Intermolecular Interaction between Indomethacin and Lidocaine

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