Complexation of celecoxib with β‐cyclodextrin: Characterization of the interaction in solution and in solid state

Sinha, Vivek Ranjan; Anitha, R.; Ghosh, Soma; Nanda, Amita; Kumria, Rachana

doi:10.1002/jps.20287

Cited by 127 publications

(53 citation statements)

References 25 publications

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“…4c, the DSC curve of Eze was characterized by a very sharp peak at 163.56°C with an onset at 163.07°C and end set at 165.74°C. The broad endotherm of HPBCD between 50°C and 110°C suggested loss of water molecules from the CD cavity [29]. AA2G and TPGS displayed peaks at 170.72°C and 40.43°C, respectively.…”

Section: Characterizationmentioning

confidence: 99%

Improved Aqueous Solubility and Antihypercholesterolemic Activity of Ezetimibe on Formulating with Hydroxypropyl-β-Cyclodextrin and Hydrophilic Auxiliary Substances

Srivalli

Mishra

2015

AAPS PharmSciTech

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Abstract. The purpose of this study was to improve the aqueous solubility, dissolution, and pharmacodynamic properties of a BCS class II drug, ezetimibe (Eze) by preparing ternary cyclodextrin complex systems. We investigated the potential synergistic effect of two novel hydrophilic auxiliary substances, D-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) and L-ascorbic acid-2-glucoside (AA2G) on hydroxypropyl-β-cyclodextrin (HPBCD) solubilization of poorly water-soluble hypocholesterolemic drug, Eze. In solution state, the binary and ternary systems were analyzed by phase solubility studies and Job's plot. The solid complexes prepared by freeze-drying were characterized by Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), powder X-ray diffraction (XRD), nuclear magnetic resonance (NMR), and scanning electron microscopy (SEM). The log P values, aqueous solubility, dissolution, and antihypercholesterolemic activity of all systems were studied. The analytical techniques confirmed the formation of inclusion complexes in the binary and ternary systems. HPBCD complexation significantly (p<0.05) reduced the log P and improved the solubility, dissolution, and hypocholesterolemic properties of Eze, and the addition of ternary component produced further significant improvement (p<0.05) even compared to binary system. The remarkable reduction in log P and enhancement in solubility, dissolution, and antihypercholesterolemic activity due to the addition of TPGS or AA2G may be attributed to enhanced wetting, dispersibility, and complete amorphization. The use of TPGS or AA2G as ternary hydrophilic auxiliary substances improved the HPBCD solubilization and antihypercholesterolemic activity of Eze.

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Section: Characterizationmentioning

confidence: 99%

Improved Aqueous Solubility and Antihypercholesterolemic Activity of Ezetimibe on Formulating with Hydroxypropyl-β-Cyclodextrin and Hydrophilic Auxiliary Substances

Srivalli

Mishra

2015

AAPS PharmSciTech

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“…The thermogram of HP-β-CD showed a very broad endothermic peak between 70°C and 100°C due to the release of water molecules present in the HP-β-CD cavity (34). When HP-β-CD interacts with a guest molecule, their melting peaks, boiling peaks, or sublimation peaks in DSC thermograms usually shift or disappear (35). DSC curves of LID/HP-β-CD physical mixtures (1:1 and 1:2) showed a decrease in endothermic peaks at 85°C, which indicated the presence of the free form of LID in physical mixtures.…”

Section: Differential Scanning Calorimetrymentioning

confidence: 99%

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

et al. 2014

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Abstract. Several attempts have been made to mask the bitter taste of oral formulations, but none have been made for injectable formulations. This study aims to mask the bitter taste of dental lidocaine HCl (LID) injection using hydroxypropyl-β-cyclodextrin (HP-β-CD) and sodium saccharin. Inclusion complexes of LID and HP-β-CD were prepared by the solution method in 1:1 and 1:2 M ratios. Inclusion complexes in solution were studied using phase solubility in phosphate buffer solutions (pH 8, 9, and 10). Freeze-dried inclusion complexes were characterized using differential scanning calorimetry (DSC), Xray, Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR), scanning electron microscopy (SEM), and in vitro release. Injectable formulations were prepared using inclusion complexes and characterized for stability and for taste using an Alpha MOS ASTREE electronic tongue (ETongue). The association constants of HP-β-CD with lidocaine-free base and its ionized form were found to be 26.23± 0.00025 and 0.8694±0.00045 M −1 , respectively. Characterization studies confirmed the formation of stable inclusion complexes of LID and HP-β-CD. Injectable formulations were found to be stable for up to 6 months at 4°C, 25°C, and 40°C. The taste evaluation study indicated that HP-β-CD (1:1 and 1:2 M ratios) significantly improved the bitter taste of LID injectable formulation. In conclusion, inclusion complex in the 1:1 M ratio with 0.09% sodium saccharin was considered to be optimum in masking the bitter taste of LID.

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“…The existence of an interaction between two components can be obtained by thermal analysis (DSC). When guest molecules are included in the CD cavity, their melting, boiling and sublimation points usually shift to a different temperature or disappear (20)(21). The value of peak area and the DELTA H value give an estimation of the number of molecules undergoing the transition (20)(21).…”

Section: Differential Scanning Calorimetrymentioning

confidence: 99%

“…When guest molecules are included in the CD cavity, their melting, boiling and sublimation points usually shift to a different temperature or disappear (20)(21). The value of peak area and the DELTA H value give an estimation of the number of molecules undergoing the transition (20)(21). Thus, the decrease in both peak area and DELTA H value for ternary complex (Table III) suggests that the complexation efficiency was enhanced due to the presence of polymer leading to a decrease in the amount of free drug in ternary complex as compared to both binary complex and physical mixture.…”

Section: Differential Scanning Calorimetrymentioning

confidence: 99%

Preparation and Evaluation of Taste Masked Famotidine Formulation Using Drug/β-cyclodextrin/Polymer Ternary Complexation Approach

Patel

Vavia

2008

AAPS PharmSciTech

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Abstract. The main aim of the present study was to evaluate potential of ternary complexation (comprising of drug, cyclodextrin and polymer) as an approach for taste masking. For this purpose famotidine with property of bitter taste was selected as a model drug. Improvement in taste masking capability of cyclodextrin towards famotidine was evaluated by formulating a ternary complex including hydrophilic polymer hydroxyl propyl methyl cellulose (HPMC 5 cps) as the third component. Phase solubility analysis at 25°C was carried out for both the binary systems (viz. drug-cyclodextrin and drugpolymer) and the ternary system (drug-cyclodextrin-polymer). Ternary complex was prepared using solution method and was further characterized using XRD, DSC, FT-IR and microscopic studies. In vitro dissolution study was carried out to see the effect of ternary complexation on drug release. Taste perception study was carried out on human volunteers to evaluate the taste masking ability of ternary complexation. Results obtained from phase solubility analysis showed that the combined use of polymer and cyclodextrin effectively increased the stability constant of the complex [from 538 M −1 for binary system to 15,096 M −1 for ternary system]. Ternary system showed effective taste masking as compared to binary complex and at the same time showed no limiting effect on the drug release (D.E 15min =90%). The effective taste masking was attributed to the enhanced complexation of famotidine in ternary system compared to binary system and the same was confirmed from the characterization studies. In conclusion, the study confirmed that ternary complexation can be utilized as an alternative approach for effective taste masking.

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Complexation of celecoxib with β‐cyclodextrin: Characterization of the interaction in solution and in solid state

Cited by 127 publications

References 25 publications

Improved Aqueous Solubility and Antihypercholesterolemic Activity of Ezetimibe on Formulating with Hydroxypropyl-β-Cyclodextrin and Hydrophilic Auxiliary Substances

Improved Aqueous Solubility and Antihypercholesterolemic Activity of Ezetimibe on Formulating with Hydroxypropyl-β-Cyclodextrin and Hydrophilic Auxiliary Substances

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

Preparation and Evaluation of Taste Masked Famotidine Formulation Using Drug/β-cyclodextrin/Polymer Ternary Complexation Approach

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