Formation of co-crystals: Kinetic and thermodynamic aspects

Gagnière, Émilie; Mangin, Denis; Puel, François; Rivoire, Alain; Monnier, Olivier; Garcia, Eric; Klein, Jean‐Paul

doi:10.1016/j.jcrysgro.2009.02.040

Cited by 102 publications

(106 citation statements)

References 9 publications

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“…The crystal obtained was collected and stored in tight container and stored in desiccators for further use. [46] Antisolvent addition method FNO (drug) and coformer were weight in 1:1 molar ratios were dissolved in 20 ml ethanol using moderate stirring. The solution was then filtered through a Whatman filter paper to remove any undissolved material.…”

Section: Slow Evaporation Methodsmentioning

confidence: 99%

“…The formed cocrystal was dried at temperature of 40°C for 48 h. The solid crystal was collected and stored in desiccators. [46] …”

Section: Slow Evaporation Methodsmentioning

confidence: 99%

“…After 6 months, the samples were withdrawn and analyzed for appearance, drug content, dissolution, Fourier transform infrared, and X-ray diffraction study. [42] Advantages of cocrystals [45,46] • Cocrystals having advantages such as stable crystalline form (as compared to amorphous solids).…”

Section: Stability Studiesmentioning

confidence: 99%

“…Applications of cocrystals [45][46][47][48][49][50] • Cocrystal engineering is relevant to production of energetic materials, pharmaceuticals, and other compounds. Of these, the most widely studied and used application is in drug development and more specifically, the formation, design, and implementation of active pharmaceutical ingredients, or API's.…”

Section: Stability Studiesmentioning

confidence: 99%

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Payghan¹

2017

AJP

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The objective of this study was to investigate whether the miscibility of a drug and coformer, as predicted by Hansen solubility parameters (HSPs), can indicate cocrystal formulation. It was also our aim to evaluate various HSPs-based approaches in miscibility predication. It is concerned with some new aspects of solvent properties, and these properties can help predict solvent behavior during the manufacturing processes and will be useful in predicting behavior in many other fields of endeavor. The work on the solubility parameter, in particular, deals with fundamental attractions among materials and should have broad application. To say that hydrogen bonding had no significant effect on solvent retention without defining hydrogen bonding was not satisfactory. To better define hydrogen bonding and polar bonding, a study based on the solubility parameter was initiated. This eventually led to the concept of a three-dimensional (3D) solubility parameter (E). The 3D solubility parameter is has been assumed that ∆E is given by the simple sum of the energies arising from dispersion forces, ∆E d , polar forces, ∆E P , and hydrogen bonding forces, ∆E h. Group contribution method for the estimation of Hansen solubility parameters of pure organic compounds is presented by characteristic groups ensure the prediction of HSP for a broad series of organic compounds, including those having complex multiring, heterocyclic, and aromatic structures. The predictions are exclusively based on the molecular structure of compounds, and no experimental data are needed. Solubility parameters for solutes are obtained by group contribution method. Using Fedor's substituent constants, Hoy's molar attraction constants and Van Kreevalen constants were calculated and are currently used methods. The resultant Δ values of active pharmaceutical ingredient and coformers are compared, and their solid-state miscibility is expressed. Possibility of cocrystal formulation by Krevlens is Δδ < 5MP and Greenhalgh Δδ < 7MP can be predicted.

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Section: Slow Evaporation Methodsmentioning

confidence: 99%

“…The formed cocrystal was dried at temperature of 40°C for 48 h. The solid crystal was collected and stored in desiccators. [46] …”

Section: Slow Evaporation Methodsmentioning

confidence: 99%

Section: Stability Studiesmentioning

confidence: 99%

Section: Stability Studiesmentioning

confidence: 99%

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Payghan¹

2017

AJP

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“…The antisolvent addition method produces small, uniform, and stable FNO cocrystal with markedly enhanced dissolution rate due to an increased solubility that is attributed to partial amorphization of drug with increased surface area and improved wettability. Analysis of molecular complexation solubility method [46] Estimation of parameter of complex [ ]…”

Section: In Vitro Dissolution Studiesmentioning

confidence: 99%

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Payghan¹

2017

AJP

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Aim: The objective of this study was to investigate whether the miscibility of a drug and coformer, as predicted by Hansen solubility parameter (HSP), can indicate cocrystal formulation. It was also our aim to evaluate various HSP-based approaches in miscibility predication. HSP for fenofibrate drug over 20 coformers was calculated according to the group contribution method. Materials and Methods: The selection of coformer was based on hydrogen bond present in structure which clearly shows the importance of hydrogen bonding in forming cocrystals. Solubility parameters for solutes are obtained by group contribution method. Result and Discussion: In the present investigation, these methods were employed to arrive at the solubility parameter values. The basic steps in Fedor's method are to open the rings and treat the resultant structure as an open-chain compound. These were sum-up, and the solubility parameter was calculated as square root of the sum of energy of mixing substituent constants divided by the sum of molar volume substituent constants. Hoy's procedure expressed in the ratio of molar attraction constant to molar volume. The resultant δ values of drug and coformers are compared, and their solid state miscibility is expressed. Possibility of cocrystal formulation by Krevelen's is Δδ < 5 MP and Greenhalgh Δδ < 7 MP. The present investigation deals with the formulation of coformer (saccharin, succinic acid, and sucrose) based on cocrystals fenofibrate by different methods and solid-state characterization of prepared cocrystals. Fenofibrate and coformers in molar ratio were used to formulate molecular complexes by solution evaporation, slow evaporation, antisolvent addition, net grinding method, and solvent-drop grinding methods. The prepared molecular complexes were characterized by powder X-ray diffraction, differential scanning calorimetry, Fourier-transform infrared spectroscopy, and in vitro dissolution study. Conclusion: Considerable improvement in the dissolution rate of fenofibrate from optimized cocrystal formulation was due to an increased solubility that is attributed to the supersaturation from the fine cocrystals which is faster due to large specific surface area of small particles and prevention of phase transformation to pure fenofibrate.

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