Imidazolium ionic liquids as solvents of pharmaceuticals: Influence on HSA binding and partition coefficient of nimesulide

Azevedo, Ana M.O.; Ribeiro, Diogo M; Pinto, Paula C.A.G.; Lúcio, Marlene; Reis, Salette; Saraiva, M. Lúcia M.F.S.

doi:10.1016/j.ijpharm.2012.12.030

Cited by 37 publications

(29 citation statements)

References 33 publications

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“…13 As a result, these solvents can be designed for a particular application or to present a particular set of intrinsic properties such as acidicity, basicity, hydrophilicity/ hydrophobicity and water miscibility, 14 as well as toxicity. 15 The combination of these excellent properties thus allows for designing green processes based on ILs. 16,17 The possibility of engineering the properties of ILs by manipulating the anion−cation combination, in association with their solvent properties and in some cases water-miscibility, makes them promising as potential pharmaceutical solvents in different situations.…”

Section: ■ Introductionmentioning

confidence: 99%

Solubility of a New Cardioactive Prototype Drug in Ionic Liquids

et al. 2014

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Solubility in different solvents is an intrinsic material characteristic for a defined molecule. The solubility of a new cardioactive prototype drug, 3,4-methylenedioxybenzoyl-2-thienylhydrazone (LASSBio-294), was determined in seven different imidazolium based ionic liquids (ILs). The ionic liquids selected were 1-ethyl-3-methylimidazolium methyl phosphonate; 1-ethyl-3-methylimidazolium ethyl phosphonate; 1-ethyl-3-methylimidazolium acetate; 1,3-dimethylimidazolium methyl phosphonate; 1-butyl-3-methylimidazolium acetate; 1-butyl-3-methylimidazolium tetrafluoroborate; and 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide. In addition, solubility data of LASSBio-294 in water and in mixtures of water and ILs were also measured. For all solvents, the concentration of drug in saturated solutions was determined by high performance liquid chromatography (HPLC). Solid−liquid equilibrium measurements were performed in a range of temperatures from 288.15 K to 308.15 K, at atmospheric pressure. From the solubility data it can be concluded that the drug showed sufficient solubility in five of the tested ILs so that these compounds can be suitable for further crystallization studies. The aim of this work is also to discuss and understand the solubility of LASSBio-294 in these alternative solvents. The results indicate that the solubility of the drug is dependent on IL structural variations (cation−anion combinations).

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Section: ■ Introductionmentioning

confidence: 99%

Solubility of a New Cardioactive Prototype Drug in Ionic Liquids

et al. 2014

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“…Furthermore, the ILs can be used as solvents for pharmaceutical components (30) and choline salts can be useful for stabilization of protein-based APIs in the formulation (31 Formulations that included SEPINEO™ P 600 resulted in high-viscosity gels or emulsion-gels. Addition of cetylstearyl alcohol as an additional thickener led to a slight increase in viscosity, in comparison to the formulation without cetylstearyl alcohol, due to the formation of a liquid crystalline phase (32).…”

Section: Discussionmentioning

confidence: 99%

Hydrophilic Ionic Liquids as Ingredients of Gel-Based Dermal Formulations

et al. 2015

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Abstract. Ionic liquids (ILs) have several properties that offer many advantages in dermal drug delivery systems. Depending on the chemical structure, ILs can be used for protection against microorganisms, to enhance skin penetration, and as a solvent. In the present work, SEPINEO™ P 600 formulations and hydroxyethylcellulose gels containing the hydrophilic ILs hexylpyridinium chloride, choline dihydrogen phosphate, and 1-ethyl-3-methylimidazolium ethyl sulfate were prepared, and the influence of the ILs on the formulation properties was evaluated. ILs were successfully incorporated into the emulsion structure, resulting in stable formulations. The antimicrobial activity of the ILs was estimated. The minimal inhibitory concentration values for hexylpyridinium chloride are about 2.5 mg/mL. The other two ILs have no antimicrobial activity. Skin penetration enhancement of caffeine, a hydrophilic model substance, was observed in the presence of hexylpyridinium chloride.

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“…8 Ao longo da última década, os LIs apresentaram enorme potencial como (co) solventes e/ou reagentes em uma ampla gama de aplicações, incluindo a Engenharia Química (separação, extração e membranas), 9 Química (síntese orgânica, reações catalíticas, síntese de nanomateriais e reações de polimerização), 10 conversão de energia (baterias, células de combustível e armazenamento de calor), 11 biotecnologia 3 Os autores agradecem ao suporte das agências de amparo à pesquisa CNPq e Fapesp. 4 Brooks (2014) Azevedo et al (2013). 9 Rao et al (2013).…”

Section: Modelagem Computacional Deunclassified

Aplicações de química teórica no estudo de materiais: métodos in silico para nanomateriais

Freitas¹,

Oliveira²

2018

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Imidazolium ionic liquids as solvents of pharmaceuticals: Influence on HSA binding and partition coefficient of nimesulide

Cited by 37 publications

References 33 publications

Solubility of a New Cardioactive Prototype Drug in Ionic Liquids

Solubility of a New Cardioactive Prototype Drug in Ionic Liquids

Hydrophilic Ionic Liquids as Ingredients of Gel-Based Dermal Formulations

Aplicações de química teórica no estudo de materiais: métodos in silico para nanomateriais

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