Inclusion complexation of weakly acidic NSAID with β-cyclodextrin: selection of arginine, an amino acid, as a novel ternary component

Bramhane, D. M.; Saindane, Nilesh S.; Vavia, Pradeep R.

doi:10.1007/s10847-010-9783-7

Cited by 25 publications

(14 citation statements)

References 14 publications

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“…Recently, arginine has been reported to possess synergistic action with hydroxypropyl-ß-cyclodextrin with respect to enhancing the aqueous solubility of naproxen (9,10). Numerous studies have reported arginine to enhance the dissolution of various drugs such as meloxicam (11), indomethacin (12), and lornoxicam (13). Exhaustive research has been carried out on dissolution enhancement of drugs using water-insoluble polymers such as crospovidone (14,15) and enteric polymers such as hydroxypropyl methylcellulose phthalate, cellulose acetate phthalate, Eudragit® L100 and S100 (16), and Eudragit® E (17,18).…”

Section: Introductionmentioning

confidence: 99%

Solid-State Characterization and Dissolution Properties of Meloxicam–Moringa Coagulant–PVP Ternary Solid Dispersions

et al. 2013

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Abstract. The effect of ternary solid dispersions of poor water-soluble NSAID meloxicam with moringa coagulant (obtained by salt extraction of moringa seeds) and polyvinylpyrrolidone on the in vitro dissolution properties has been investigated. Binary (meloxicam-moringa and meloxicam-polyvinylpyrrolidone (PVP)) and ternary (meloxicam-moringa-PVP) systems were prepared by physical kneading and ball milling and characterized by Fourier transform infrared spectroscopy, differential scanning calorimetry, and X-ray diffractometry. The in vitro dissolution behavior of meloxicam from the different products was evaluated by means of United States Pharmacopeia type II dissolution apparatus. The results of solid-state studies indicated the presence of strong interactions between meloxicam, moringa, and PVP which were of totally amorphous nature. All ternary combinations were significantly more effective than the corresponding binary systems in improving the dissolution rate of meloxicam. The best performance in this respect was given by the ternary combination employing meloxicam-moringa-PVP ratio of [1:(3:1)] prepared by ball milling, with about six times increase in percent dissolution rate, whereas meloxicam-moringa (1:3) and meloxicam-PVP (1:4) prepared by ball milling improved dissolution of meloxicam by almost 3-and 2.5-folds, respectively. The achieved excellent dissolution enhancement of meloxicam in the ternary systems was attributed to the combined effects of impartation of hydrophilic characteristic by PVP, as well as to the synergistic interaction between moringa and PVP.

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Section: Introductionmentioning

confidence: 99%

Solid-State Characterization and Dissolution Properties of Meloxicam–Moringa Coagulant–PVP Ternary Solid Dispersions

et al. 2013

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“…2 shows the phase solubility curves of bosentan monohydrate in presence and/or in absence of all ternary auxiliary substances. The solubility of pure drug increased with increasing the concentration of β-cyclodextrin, indicating A L type of phase solubility curve with remarkable enhancement in aqueous solubility of bosentan monohydrate [9,11]. The possible stoichiometries for all systems were found to be 1:1.…”

Section: Resultsmentioning

confidence: 91%

“…Despite the wide applications, unfortunately, β-cyclodextrin suffers from lower complexation efficiency, allowing its large amount to be incorporated during formulation, thus, adversely affecting its practical usefulness [7,8]. However, the complexation efficiency can be improved by the use of certain water-soluble auxiliary substances such as hydrophilic polymers [7,8] hydroxy acids [9] and/or amino acids [10][11][12][13] to the complexation media. Therefore, it was decided to investigate the effect of various auxiliary substances, theoretically as well as practically, on the complexation efficiency of β-cyclodextrin towards bosentan monohydrate.…”

Section: Introductionmentioning

confidence: 99%

in silico and Physico-Chemical Assessment of Effectiveness of Hydroxy/Amino Acids as Auxiliary Substances to Improve the Complexation Efficiency of ββ ββ β-Cyclodextrin Towards Bosentan

Pore¹,

Jadhav²

2017

Asian J. Chem.

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The effectiveness of certain hydroxy and amino acids as an auxiliary substance to improve the complexation efficiency of β-cyclodextrin towards bosentan, a poorly soluble endothelin receptor antagonist, were assessed to enhance its physico-chemical performance. The phase solubility studies conducted in distilled water demonstrated a better choice of L-arginine as an auxiliary substance to improve complexation efficiency and association constant (Ks) of β-cyclodextrin. As a complementary evidence, in silico calculations were performed to foresee the stability, possible interactions and geometry of bosentan monohydrate inside β-cyclodextrin cavity, optimizing L-arginine again as an auxiliary substance. Subsequently, the solution state thermodynamic investigations revealed entropy driven complexation process. The lyophilized complexes were characterized by FTIR, DSC, XRPD and SEM. The performance of ternary complex was found to be appreciating in overall assessment, indicating better effectiveness of L-arginine as an auxiliary substance in improving complexation efficiency of β-cyclodextrin towards bosentan monohydrate.

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“…Alternately, if association takes place at the exterior of the torus (surface interaction), H-1, H-2, H-4 and H-6 will be strongly shielded (12). The H-3 triplet of b-CD appears at d 3.891 along with H-5 and H-6 at d 3.822 and 3.808, respectively.…”

Section: Effect Of Formulation Variablesmentioning

confidence: 99%

“…Efficient delivery of this poorly water-soluble drug was achieved by increasing its solubility, which resulted in dissolution enhancement. One of the methods used to increase the solubility of a poorly water-soluble drug is the cyclodextrin complexation technique (11,12). The proposed mechanism by which this solubilisation occurs is the inclusion complex formation, in which there is dynamic equilibrium between the guest and host molecules with the complex (13,14).…”

mentioning

confidence: 99%

Felodipine β-cyclodextrin complex as an active core for time delayed chronotherapeutic treatment of hypertension

Pagar

Vavia²

2012

Acta Pharmaceutica

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The key to the success of any drug delivery system depends upon the development of formulations that accomplish the therapeutic needs associated with a particular pathological condition or disease state (1). Many physiological body functions (e.g., blood The present research work deals with the development of a time delayed chronotherapeutic formulation of felodipine (FD) aimed at rapid drug release after a desired lag time in the management of hypertension. The developed system comprises a drug core embedded within a swellable layer and coated with an insoluble, water permeable polymeric system. FD cyclodextrin complex was used as an active core while ethyl cellulose was used as an effective coating layer. Dissolution studies of the complex revealed that there was a 3-fold increase in dissolution of the complex compared to plain FD. This dissolution enhancement and rapid drug release resulted from FD amorphisation, as confirmed by XRD, DSC and SEM studies. FTIR and 1 H NMR studies confirmed the complex formation between FD and cyclodextrin based on the observed hydrogen bond interactions. FD release was adequately adjusted by using a pH independent polymer, i.e., ethyl cellulose, along with dibutyl phthalate as plasticizer. Influence of formulation variables like polymer viscosity, plasticizer concentration, super disintegrant concentration in the swellable layer and percent coating weight gain was investigated to characterize the lag time. Upon permeation of water, the core tablet swelled, resulting in the rupture of the coating layer, followed by rapid drug release. The developed formulation of FD showed a lag time of 5-7 h, which is desirable for chronotherapeutic application.

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Inclusion complexation of weakly acidic NSAID with β-cyclodextrin: selection of arginine, an amino acid, as a novel ternary component

Cited by 25 publications

References 14 publications

Solid-State Characterization and Dissolution Properties of Meloxicam–Moringa Coagulant–PVP Ternary Solid Dispersions

Solid-State Characterization and Dissolution Properties of Meloxicam–Moringa Coagulant–PVP Ternary Solid Dispersions

in silico and Physico-Chemical Assessment of Effectiveness of Hydroxy/Amino Acids as Auxiliary Substances to Improve the Complexation Efficiency of ββ ββ β-Cyclodextrin Towards Bosentan

Felodipine β-cyclodextrin complex as an active core for time delayed chronotherapeutic treatment of hypertension

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