Effect of cocrystallization techniques on compressional properties of caffeine/oxalic acid 2:1 cocrystal

Aher, Suyog; Dhumal, Ravindra S.; Mahadik, Kakasaheb R.; Ketolainen, Jarkko; Paradkar, Anant

doi:10.3109/10837450.2011.618950

Cited by 24 publications

(16 citation statements)

References 25 publications

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“…Many studies have shown that co-crystals improve the solubility in water and dissolution rates of parent compounds [9][10][11], and moreover, co-crystals can affect other physico-chemical properties of the same drug. In the literature can be found a description of an increase in physical and chemical stability or improvement in mechanical properties [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

“…Solvent evaporation, slurry conversion and cooling crystallisation are examples of traditional solutionbased methods [12,14]. The recent literature provides various modifications of solution-based methods such as approaches using supercritical fluid technology [17] or an ultrasound-assisted solution process [13]. As solid-state and solution-based methods have some drawbacks [15], attempts at co-crystal formation are usually conducted using both methods together in order to obtain co-crystals with the most suitable properties, at least in the opinion of the researchers.…”

Section: Introductionmentioning

confidence: 99%

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DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Saganowska

Wesołowski

2017

J Therm Anal Calorim

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In recent years, co-crystals have been the subject of increasing interest within the pharmaceutical industry because these new solid forms of active pharmaceutical ingredients have the ability to enhance the bioavailability of poorly water-soluble drugs with a low dissolution rate. For this reason, it is crucial to prepare co-crystals of benzodiazepines, i.e. psychoactive drugs with a wide range of medical applications but classified as very slightly or practically insoluble in water. Thus, the objective of this research was to show to what extent the DSC method can be used as a screening tool for detection of cocrystal formation in binary physical mixtures of drugs and co-formers. To obtain potential co-crystals, eight benzodiazepines (diazepam, temazepam, oxazepam, lormetazepam, lorazepam, clonazepam, estazolam and chlordiazepoxide) were gently mixed in an agate mortar at 1:1 molar ratios with nine co-formers-succinic, glutaric, fumaric, citric and paminobenzoic acids, nicotinamide, saccharin, urea and caffeine, and heated under DSC conditions. A detailed comparison of the DSC scans of mixtures against scans of both ingredients in isolation indicates the occurrence of subtle physical changes in the samples. Thus, additional endothermic or exothermic peaks due to melting or crystallisation suggested the formation of potential co-crystals. To conclude, this study confirms that the DSC method can be used as a rapid screening tool for co-crystal detection. In this case, based on the DSC scans, 15 physical mixtures of benzodiazepines (clonazepam, diazepam, lorazepam, oxazepam and temazepam) with co-formers (citric, fumaric, glutaric, p-aminobenzoic and succinic acids, nicotinamide, saccharin and urea) have been selected as potential co-crystals for further detailed study.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Saganowska

Wesołowski

2017

J Therm Anal Calorim

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“…The batch mode cocrystallization techniques include mechanochemical methods such as Solid-State grinding [ 151 , 152 ], Liquid-Assisted grinding [ 151 ], Ion and Liquid-Assisted Grinding [ 153 ] and solvent-based techniques such as slow evaporation [ 154 ], ultrasound-assisted cocrystallization [ 155 , 156 ], slurry conversion [ 140 , 157 ] or solvent-mediated phase transformation [ 158 ], generation of cocrystals from moisture [ 159 , 160 ] and anti-solvent precipitation (Liquid Anti-Solvent precipitation) [ 161 ] and Gas Anti-Solvent precipitation [ 162 ]. Table 7 presents the principle involved behind these batch cocrystallization techniques [ 151 , 153 , 154 , 155 , 159 , 161 , 162 , 163 ].…”

Section: Synthesis Of Cocrystalsmentioning

confidence: 99%

“…Ultrasound can therefore induce crystallization easily from solution which otherwise is difficult to attain by conventional solution crystallization experiments [ 155 ]. Reports are available in the literature where ultrasound-assisted solution cocrystallization (USSC) [ 60 , 155 , 156 , 177 ] has been reported as a method to crystallize caffeine-maleic acid (2:1) [ 155 ] and caffeine-oxalic acid (2:1) [ 155 , 156 ].…”

Section: Synthesis Of Cocrystalsmentioning

confidence: 99%

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

2018

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Biopharmaceutics Classification System (BCS) Class II and IV drugs suffer from poor aqueous solubility and hence low bioavailability. Most of these drugs are hydrophobic and cannot be developed into a pharmaceutical formulation due to their poor aqueous solubility. One of the ways to enhance the aqueous solubility of poorlywater-soluble drugs is to use the principles of crystal engineering to formulate cocrystals of these molecules with water-soluble molecules (which are generally called coformers). Many researchers have shown that the cocrystals significantly enhance the aqueous solubility of poorly water-soluble drugs. In this review, we present a consolidated account of reports available in the literature related to the cocrystallization of poorly water-soluble drugs. The current practice to formulate new drug cocrystals with enhanced solubility involves a lot of empiricism. Therefore, in this work, attempts have been made to understand a general framework involved in successful (and unsuccessful) cocrystallization events which can yield different solid forms such as cocrystals, cocrystal polymorphs, cocrystal hydrates/solvates, salts, coamorphous solids, eutectics and solid solutions. The rationale behind screening suitable coformers for cocrystallization has been explained based on the rules of five i.e., hydrogen bonding, halogen bonding (and in general non-covalent bonding), length of carbon chain, molecular recognition points and coformer aqueous solubility. Different techniques to screen coformers for effective cocrystallization and methods to synthesize cocrystals have been discussed. Recent advances in technologies for continuous and solvent-free production of cocrystals have also been discussed. Furthermore, mechanisms involved in solubilization of these solid forms and the parameters influencing dissolution and stability of specific solid forms have been discussed. Overall, this review provides a consolidated account of the rationale for design of cocrystals, past efforts, recent developments and future perspectives for cocrystallization research which will be extremely useful for researchers working in pharmaceutical formulation development.

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“…The formation of co-crystals involves combining drugs with pharmaceutically acceptable additives in the crystal lattice. The resulting multicomponent crystal form will have different physicochemical properties and can potentially improve solubility [7,8], dissolution rate [9,10], compressibility [11], chemical and physical stability [12].…”

Section: Introductionmentioning

confidence: 99%

Solubility Enhancement of Clozapine Through Co-Crystal Formation with Isonicotinamide

et al. 2019

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Clozapine (CLO) is an effective atypical antipsychotic to control the symptoms of psychosis and schizophrenia. Clozapine has low solubility and high permeability, so it is classified as a class II in the biopharmaceutical classification system. The aim of this study was to improve the solubility and dissolution rate of clozapine by clozapine-isonicotinamide (CLO-INA) co-crystal formation. CLO-INA co-crystal was prepared by solvent-drop grinding (SDG) method using water as a solvent. Characterization of SDG result was conducted by powder X-ray diffraction (PXRD) and Fourier transform infrared (FTIR). Solubility test was performed in water at room temperature. The dissolution test was performed in 900 mL of pH 6.8 phosphate buffer solution, 50 rotation per minute of paddle rotation, and at 37±0.5 °C. The PXRD pattern of SDG result of CLO-INA has many different peaks from its parent components, and this may indicate the co-crystal formation. The solubility of the co-crystal clozapine was fifteen folds higher than pure clozapine. The dissolution rate of CLO-INA co-crystal increased in the first 10 minutes compared to pure clozapine. Percentage of clozapine dissolved after 10 minutes from CLO-INA co-crystal and pure CLO were 10.2 and 2.4%, respectively. CLO and INA can form co-crystal by SDG method that can improve the solubility and dissolution rate of clozapine.Keywords: Clozapine, Isonicotinamide, Co-crystal, Solubility, Dissolution

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Effect of cocrystallization techniques on compressional properties of caffeine/oxalic acid 2:1 cocrystal

Cited by 24 publications

References 25 publications

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

Solubility Enhancement of Clozapine Through Co-Crystal Formation with Isonicotinamide

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