The third evolution of ionic liquids: active pharmaceutical ingredients

Hough, Whitney L.; Śmiglak, Marcin; Rodríguez, Héctor; Swatloski, Richard P.; Spear, Scott K.; Daly, Daniel T.; Pernak, Juliusz; Grisel, Judith E.; Carliss, Richard D.; Soutullo, Morgan D.; Davis, James H.; Rogers, Robin D.

doi:10.1039/b706677p

Cited by 767 publications

(649 citation statements)

References 26 publications

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“…The first attempt to specifically prepare active pharmaceutical ionic liquids (API-ILs) was accomplished by Rogers and co-workers (Hough et al, 2007), who developed the potential scope of this poorly exploited drug phase. Since then, API-ILs have been studied by a number of groups.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

102

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a b s t r a c tIn order to overcome the problems associated with low water solubility, and consequently low bioavailability of active pharmaceutical ingredients (APIs), herein we explore a modular ionic liquid synthetic strategy for improved APIs. Ionic liquids containing l-ampicillin as active pharmaceutical ingredient anion were prepared using the methodology developed in our previous work, using organic cations selected from substituted ammonium, phosphonium, pyridinium and methylimidazolium salts, with the intent of enhancing the solubility and bioavailability of l-ampicillin forms. In order to evaluate important properties of the synthesized API-ILs, the water solubility at 25 • C and 37 • C (body temperature) as well as octanol-water partition coefficients (K ow 's) and HDPC micelles partition at 25 • C were measured. Critical micelle concentrations (CMC's) in water at 25 • C and 37 • C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements.

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Section: Introductionmentioning

confidence: 99%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

102

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“…This dual functionality inherent in ILs is rarely exploited, 67,68 and we have only recently published our first paper with the designed incorporation of two biologically active ions into an IL. 69 Given that polymorphism and solvate formation cannot be predicted; that the exact crystalline state affects chemical (e.g., dissolution rate, solubility), biological (e.g., bioavailability, pharmacokinetics), mechanical, and physical properties, as well as, manufacturing processes; and that polymorphs and solvates may inconveniently interconvert-what are needed are chemical compositions that a) are effective for their intended purpose; b) have controlled and tunable chemical, biological, and physical properties, c) are in a form that is not subject to polymorphism, and d) for which controlled tunable dissolution and solubility are possible. In other words, ionic liquids.…”

Section: Ionic Liquids As Active Pharmaceutical Ingredients (Apis)mentioning

confidence: 99%

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Hough¹,

Rogers²

2007

Bulletin of the Chemical Society of Japan

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318

219

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Ionic liquids (ILs) have evolved from salts studied primarily for their physical properties (low melting salts which could be used as solvents) to tunable materials based upon the physical, chemical, and now even biological properties that can be introduced through either ion. In this perspective, we follow this interesting evolution with respect to our work in this growing field, and discuss possible future directions, such as the use of ILs as active pharmaceutical ingredients (APIs).

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“…ILs have received considerable attention for a wide range of applications, across catalysis reactions, electrochemistry, separation science, polymer chemistry, formulation of pharmaceutical drugs, amongst others (81,82). The reader is invited to consult several reviews available in the literature to have a wider insight on this matter.…”

Section: Introduction To Ionic Liquidsmentioning

confidence: 99%