An investigation of flurbiprofen polymorphism by thermoanalytical and spectroscopic methods and a study of its interactions with poly-(ethylene glycol) 6000 by differential scanning calorimetry and modelling

Lacoulonche, F.; Chauvet, Alain; Masse, J.

doi:10.1016/s0378-5173(97)00102-6

Cited by 26 publications

(30 citation statements)

References 12 publications

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“…The FTIR spectra of the three modifications show significant differences. Compared with the IR spectra published by Lacoulonche et al, 2 it is clear that our mod. I corresponds to their form I and our mod.…”

Section: Discussionsupporting

confidence: 61%

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Demonstration of the Terms Enantiotropy and Monotropy in Polymorphism Research Exemplified by Flurbiprofen

Henck

Kuhnert-Brandstätter

1999

Journal of Pharmaceutical Sciences

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The thermodynamic terms enantiotropy and monotropy are demonstrated by means of solid-state analytical results of polymorphous flurbiprofen (FBP). Vibrational spectra, differential scanning calorimetry (DSC), and thermomicroscopy investigations as well as X-ray powder patterns for three modifications of FBP are described. The melting points are mod. I 113-114 degreesC (enthalpy of fusion 27.9 +/- 0.2 kJ mol-1) for modification I (mod. I), 92 degreesC for mod. II, and 87 degreesC for mod. III. The true densities of mod. I (1.279 +/- 0.001 g cm-3) and mod. II (1.231 +/- 0.002 g cm-3) were measured at 25 degreesC. Modification I (commercial product) is the thermodynamically stable crystal form from absolute zero to its melting point. Modification II was crystallized on a gram scale from a warm saturated solution of FBP in n-heptane and rapid cooling of the solution to -18 degreesC. Modification I is monotropically related to mod. II and mod. III, due to application of the density rule and the entropy-of-fusion rule. The thermodynamic relationships between the three modifications are demonstrated by a semischematic energy/temperature diagram. Theoretical vapor pressure/temperature diagrams and energy/temperature diagrams are compared and briefly discussed.

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Section: Discussionsupporting

confidence: 61%

“…Even today, some authors working in this area seem to have great trouble with these terms, as has been shown by recent publications in respected journals on chloramphenicol palmitate 1 and flurbiprofen. 2 Two pharmaceutically relevant modifications, mod. I (A) and mod.…”

Section: Introductionmentioning

confidence: 99%

Demonstration of the Terms Enantiotropy and Monotropy in Polymorphism Research Exemplified by Flurbiprofen

Henck

Kuhnert-Brandstätter

1999

Journal of Pharmaceutical Sciences

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“…Application of the fusion technique in the production of eutectics [30,[46][47][48][49][50] requires that a mixture of the two components be heated above the melting temperature of the highest melting component. The two miscible liquids are mixed until homogenous, and controlled solidification is facilitated by cooling the liquid mixture through T e .…”

Section: Eutecticsmentioning

confidence: 99%

Aqueous Solubility Enhancement Through Engineering of Binary Solid Composites: Pharmaceutical Applications

Moore

Wildfong

2009

J Pharm Innov

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Limits to the aqueous solubility of emerging new chemical entities, as well as older drug molecules, represent a barrier to solid oral dosage form development. Numerous techniques are conventionally employed in aqueous solubility enhancement, although a universal strategy has proven elusive. Formation of binary solid composites, such as eutectics or amorphous solid dispersions, offers an alternative to traditional solubility enhancement techniques. The reality of these systems, however, is that very few examples have been made commercially available, ultimately stemming from a lack of understanding regarding structural and thermodynamic stability-indicating phenomena associated with higher-energy solid materials. In the present work, a comprehensive structurally based review of the fundamental solid-state properties of binary composite materials is presented. Specific emphasis is placed on current topics of research in the area of binary composite formation and the relationship to the underutilization of this technology with the pharmaceutical industry.

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“…Flurbiprofen, (RS)-2-(2-fluorobiphenyl-4-yl) propanoic acid, contains a biphenyl group and a fluorine atom at the ortho position of the second biphenyl ring (see Figure 1), has a pKa value of 4.22 (Lacoulonche et al 1997), melting point of 115 °C and a molecular weight of 244.26 g/mol.…”

Section: Methodsmentioning

confidence: 99%

The influence of salt formation on electrostatic and compression properties of flurbiprofen salts

Šupuk

Ghori

Asare-Addo

et al. 2013

International Journal of Pharmaceutics

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Salt formation is an effective method of improving physicochemical properties of acidic and basic drugs. The selection of a salt form most suitable for drug development requires a welldesigned screening strategy to ensure various issues are addressed in the early development stages.Triboelectrification of pharmaceutical powders may cause problems during processing such as segregation of components due to the effects of particle adhesion. However, very little work has been done on the effect of salt formation on triboelectrification properties. In this paper, salts of flurbiprofen were prepared by combining the drug with a selection of closely related amine counterions. The aim of the work was to investigate the impact of the counter ion on electrostatic charge of the resultant salts to inform the salt selection process. The experimental results show the magnitude of charge and polarity of the flurbiprofen salts to be highly dependent on the type of counter ion selected for the salt formation. Furthermore, particle adhesion to the stainless steel surface of the shaking container and the salts' compression properties were measured. The formed salts had lower electrostatic charges, improved tabletability, and resulted in reduced adhesion of these powders compared with the parent drug.

show abstract

An investigation of flurbiprofen polymorphism by thermoanalytical and spectroscopic methods and a study of its interactions with poly-(ethylene glycol) 6000 by differential scanning calorimetry and modelling

Cited by 26 publications

References 12 publications

Demonstration of the Terms Enantiotropy and Monotropy in Polymorphism Research Exemplified by Flurbiprofen

Demonstration of the Terms Enantiotropy and Monotropy in Polymorphism Research Exemplified by Flurbiprofen

Aqueous Solubility Enhancement Through Engineering of Binary Solid Composites: Pharmaceutical Applications

The influence of salt formation on electrostatic and compression properties of flurbiprofen salts

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