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Janko Zmitek - One of the best experts on this subject based on the ideXlab platform.
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anti inflammatory analgesic and ulcerogenic properties of s Ibuproxam racemic Ibuproxam β cyclodextrin and s Ibuproxam β cyclodextrin
Journal of Pharmacy and Pharmacology, 1996Co-Authors: Breda Bolevunduk, Katarina Verhnjak, Janko ZmitekAbstract:The anti-inflammatory, analgesic and gastric mucosal damage-inducing activities of S-(+)-Ibuproxam, and S-(+)-Ibuproxam-beta-cyclodextrin, new propionic acid derivatives, and racemic Ibuproxam-beta-cyclodextrin were investigated in three animal models and compared with those of racemic Ibuproxam, racemic ibuprofen and its optical enantiomer S-(+)-ibuprofen. The anti-inflammatory activities of racemic ibuprofen, S-(+)-ibuprofen and racemic Ibuproxam in carrageenan-induced paw oedema in rats were almost equipotent and slightly greater than those of S-(+)-Ibuproxam and S-(+)-Ibuproxam-beta-cyclodextrin, and significantly greater than that of racemic Ibuproxam-beta-cyclodextrin. In abdominal constriction tests in mice, the analgesic effects of racemic Ibuproxam, S-(+)-Ibuproxam, racemic Ibuproxam-beta-cyclodextrin and S-(+)-Ibuproxam-beta-cyclodextrin were significantly less pronounced than those of racemic ibuprofen and S-(+)-ibuprofen. Ulcerogenic activity of S-(+)-Ibuproxam-beta-cyclodextrin in rats was found to be significantly weaker than that of racemic Ibuproxam-beta-cyclodextrin, racemic Ibuproxam and S-(+)-Ibuproxam and, most notably, weaker than those of racemic ibuprofen and S-(+)ibuprofen. These results indicate that S-(+)-Ibuproxam-beta-cyclodextrin could be a novel potent anti-inflammatory and analgesic agent with a therapeutic index more favourable than that of the classical non-steroid anti-inflammatory drugs ibuprofen and Ibuproxam.
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Anti‐inflammatory, Analgesic and Ulcerogenic Properties of S‐(+)‐Ibuproxam, Racemic Ibuproxam‐β‐cyclodextrin and S‐(+)‐Ibuproxam‐β‐cyclodextrin
The Journal of pharmacy and pharmacology, 1996Co-Authors: Breda Bole-vunduk, Katarina Verhnjak, Janko ZmitekAbstract:The anti-inflammatory, analgesic and gastric mucosal damage-inducing activities of S-(+)-Ibuproxam, and S-(+)-Ibuproxam-beta-cyclodextrin, new propionic acid derivatives, and racemic Ibuproxam-beta-cyclodextrin were investigated in three animal models and compared with those of racemic Ibuproxam, racemic ibuprofen and its optical enantiomer S-(+)-ibuprofen. The anti-inflammatory activities of racemic ibuprofen, S-(+)-ibuprofen and racemic Ibuproxam in carrageenan-induced paw oedema in rats were almost equipotent and slightly greater than those of S-(+)-Ibuproxam and S-(+)-Ibuproxam-beta-cyclodextrin, and significantly greater than that of racemic Ibuproxam-beta-cyclodextrin. In abdominal constriction tests in mice, the analgesic effects of racemic Ibuproxam, S-(+)-Ibuproxam, racemic Ibuproxam-beta-cyclodextrin and S-(+)-Ibuproxam-beta-cyclodextrin were significantly less pronounced than those of racemic ibuprofen and S-(+)-ibuprofen. Ulcerogenic activity of S-(+)-Ibuproxam-beta-cyclodextrin in rats was found to be significantly weaker than that of racemic Ibuproxam-beta-cyclodextrin, racemic Ibuproxam and S-(+)-Ibuproxam and, most notably, weaker than those of racemic ibuprofen and S-(+)ibuprofen. These results indicate that S-(+)-Ibuproxam-beta-cyclodextrin could be a novel potent anti-inflammatory and analgesic agent with a therapeutic index more favourable than that of the classical non-steroid anti-inflammatory drugs ibuprofen and Ibuproxam.
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Synthesis of (+)‐(S)‐Ibuproxam and preparation of some new complexes of racemic and (+)‐(S)‐Ibuproxam with β‐cyclodextrin and its derivatives
Chirality, 1995Co-Authors: Janko Zmitek, Katarina Verhnjak, Uros Urleb, Sonja KotnikAbstract:(+)-(S)-Ibuproxam, a prodrug of (+)-(S)-ibuprofen, the pharmacologically active component of ibuprofen, was synthesized in order to minimize side effects (especially gastric irritation) and reduce effective dose. The low water solubility of (+)-(S)-Ibuproxam, which prevents rapid dissolution and absorption from the gastrointestinal tract, was overcome by complexation with β-cyclodextrin and its derivatives. The inclusion complex formation was confirmed by differential scanning calorimetry (DSC), by 1H-NMR spectroscopy, and X-ray powder diffractometry. The physicochemical characteristics of Ibuproxam were significantly improved by the complexation. © 1995 Wiley-Liss, Inc.
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synthesis of s Ibuproxam and preparation of some new complexes of racemic and s Ibuproxam with β cyclodextrin and its derivatives
Chirality, 1995Co-Authors: Janko Zmitek, Katarina Verhnjak, Uros Urleb, Sonja KotnikAbstract:(+)-(S)-Ibuproxam, a prodrug of (+)-(S)-ibuprofen, the pharmacologically active component of ibuprofen, was synthesized in order to minimize side effects (especially gastric irritation) and reduce effective dose. The low water solubility of (+)-(S)-Ibuproxam, which prevents rapid dissolution and absorption from the gastrointestinal tract, was overcome by complexation with β-cyclodextrin and its derivatives. The inclusion complex formation was confirmed by differential scanning calorimetry (DSC), by 1H-NMR spectroscopy, and X-ray powder diffractometry. The physicochemical characteristics of Ibuproxam were significantly improved by the complexation. © 1995 Wiley-Liss, Inc.
Katarina Verhnjak - One of the best experts on this subject based on the ideXlab platform.
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anti inflammatory analgesic and ulcerogenic properties of s Ibuproxam racemic Ibuproxam β cyclodextrin and s Ibuproxam β cyclodextrin
Journal of Pharmacy and Pharmacology, 1996Co-Authors: Breda Bolevunduk, Katarina Verhnjak, Janko ZmitekAbstract:The anti-inflammatory, analgesic and gastric mucosal damage-inducing activities of S-(+)-Ibuproxam, and S-(+)-Ibuproxam-beta-cyclodextrin, new propionic acid derivatives, and racemic Ibuproxam-beta-cyclodextrin were investigated in three animal models and compared with those of racemic Ibuproxam, racemic ibuprofen and its optical enantiomer S-(+)-ibuprofen. The anti-inflammatory activities of racemic ibuprofen, S-(+)-ibuprofen and racemic Ibuproxam in carrageenan-induced paw oedema in rats were almost equipotent and slightly greater than those of S-(+)-Ibuproxam and S-(+)-Ibuproxam-beta-cyclodextrin, and significantly greater than that of racemic Ibuproxam-beta-cyclodextrin. In abdominal constriction tests in mice, the analgesic effects of racemic Ibuproxam, S-(+)-Ibuproxam, racemic Ibuproxam-beta-cyclodextrin and S-(+)-Ibuproxam-beta-cyclodextrin were significantly less pronounced than those of racemic ibuprofen and S-(+)-ibuprofen. Ulcerogenic activity of S-(+)-Ibuproxam-beta-cyclodextrin in rats was found to be significantly weaker than that of racemic Ibuproxam-beta-cyclodextrin, racemic Ibuproxam and S-(+)-Ibuproxam and, most notably, weaker than those of racemic ibuprofen and S-(+)ibuprofen. These results indicate that S-(+)-Ibuproxam-beta-cyclodextrin could be a novel potent anti-inflammatory and analgesic agent with a therapeutic index more favourable than that of the classical non-steroid anti-inflammatory drugs ibuprofen and Ibuproxam.
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Anti‐inflammatory, Analgesic and Ulcerogenic Properties of S‐(+)‐Ibuproxam, Racemic Ibuproxam‐β‐cyclodextrin and S‐(+)‐Ibuproxam‐β‐cyclodextrin
The Journal of pharmacy and pharmacology, 1996Co-Authors: Breda Bole-vunduk, Katarina Verhnjak, Janko ZmitekAbstract:The anti-inflammatory, analgesic and gastric mucosal damage-inducing activities of S-(+)-Ibuproxam, and S-(+)-Ibuproxam-beta-cyclodextrin, new propionic acid derivatives, and racemic Ibuproxam-beta-cyclodextrin were investigated in three animal models and compared with those of racemic Ibuproxam, racemic ibuprofen and its optical enantiomer S-(+)-ibuprofen. The anti-inflammatory activities of racemic ibuprofen, S-(+)-ibuprofen and racemic Ibuproxam in carrageenan-induced paw oedema in rats were almost equipotent and slightly greater than those of S-(+)-Ibuproxam and S-(+)-Ibuproxam-beta-cyclodextrin, and significantly greater than that of racemic Ibuproxam-beta-cyclodextrin. In abdominal constriction tests in mice, the analgesic effects of racemic Ibuproxam, S-(+)-Ibuproxam, racemic Ibuproxam-beta-cyclodextrin and S-(+)-Ibuproxam-beta-cyclodextrin were significantly less pronounced than those of racemic ibuprofen and S-(+)-ibuprofen. Ulcerogenic activity of S-(+)-Ibuproxam-beta-cyclodextrin in rats was found to be significantly weaker than that of racemic Ibuproxam-beta-cyclodextrin, racemic Ibuproxam and S-(+)-Ibuproxam and, most notably, weaker than those of racemic ibuprofen and S-(+)ibuprofen. These results indicate that S-(+)-Ibuproxam-beta-cyclodextrin could be a novel potent anti-inflammatory and analgesic agent with a therapeutic index more favourable than that of the classical non-steroid anti-inflammatory drugs ibuprofen and Ibuproxam.
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Synthesis of (+)‐(S)‐Ibuproxam and preparation of some new complexes of racemic and (+)‐(S)‐Ibuproxam with β‐cyclodextrin and its derivatives
Chirality, 1995Co-Authors: Janko Zmitek, Katarina Verhnjak, Uros Urleb, Sonja KotnikAbstract:(+)-(S)-Ibuproxam, a prodrug of (+)-(S)-ibuprofen, the pharmacologically active component of ibuprofen, was synthesized in order to minimize side effects (especially gastric irritation) and reduce effective dose. The low water solubility of (+)-(S)-Ibuproxam, which prevents rapid dissolution and absorption from the gastrointestinal tract, was overcome by complexation with β-cyclodextrin and its derivatives. The inclusion complex formation was confirmed by differential scanning calorimetry (DSC), by 1H-NMR spectroscopy, and X-ray powder diffractometry. The physicochemical characteristics of Ibuproxam were significantly improved by the complexation. © 1995 Wiley-Liss, Inc.
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synthesis of s Ibuproxam and preparation of some new complexes of racemic and s Ibuproxam with β cyclodextrin and its derivatives
Chirality, 1995Co-Authors: Janko Zmitek, Katarina Verhnjak, Uros Urleb, Sonja KotnikAbstract:(+)-(S)-Ibuproxam, a prodrug of (+)-(S)-ibuprofen, the pharmacologically active component of ibuprofen, was synthesized in order to minimize side effects (especially gastric irritation) and reduce effective dose. The low water solubility of (+)-(S)-Ibuproxam, which prevents rapid dissolution and absorption from the gastrointestinal tract, was overcome by complexation with β-cyclodextrin and its derivatives. The inclusion complex formation was confirmed by differential scanning calorimetry (DSC), by 1H-NMR spectroscopy, and X-ray powder diffractometry. The physicochemical characteristics of Ibuproxam were significantly improved by the complexation. © 1995 Wiley-Liss, Inc.
Charles Martin Heard - One of the best experts on this subject based on the ideXlab platform.
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Enantiomeric resolution of some 2-arylpropionic acids using L-(-)-serine-impregnated silica as stationary phase by thin layer chromatography.
Journal of Pharmaceutical and Biomedical Analysis, 2003Co-Authors: Hassan Y. Aboul-enein, Mahmoud I. El-awady, Charles Martin HeardAbstract:The enantiomeric resolution of certain 2-arylpropionic acids was achieved on thin silica gel plates impregnated with optically pure l-(−)-serine as chiral selector. The mobile phase enabling successful resolution of (±)-Ibuproxam and (±)-ketoprofen was acetonitrile–methanol–water (16:4:0.5, v/v/v) and (16:3:0.5, v/v/v) for (±)-tiaprofenic acid. The spots were detected with iodine vapors and the detection limits were found to be different for each of the 2-arylpropionic acid, ranging between 0.25 and 0.50 μg/ml. The effect of concentration of the impregnating chiral selector, temperature and pH on resolution has been studied. The procedure was applied successfully to resolve commercial ampoules of ketoprofen dosage formulation.
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Thin layer chromatographic resolution of some 2‐arylpropionic acid enantiomers using L‐(−)‐serine, L‐(−)‐threonine and a mixture of L‐(−)‐serine and L‐(−)‐threonine‐impregnated silica gel as stationary phases
Biomedical chromatography : BMC, 2003Co-Authors: Hassan Y. Aboul-enein, Mahmoud I. El-awady, Charles Martin HeardAbstract:Impregnated silica TLC plates with L-(−)-serine and L-(−)-threonine and a mixture of L-(−)-serine and L-(−)-threonine (1:1) as chiral selectors were prepared to use as chiral stationary phases (CSPs) in thin layer chromatography. The resolution of the enantiomers of 2-arylpropionic drugs, including ibuprofen, Ibuproxam, ketoprofen, pranoprofen, benoxaprofen, flurbiprofen and tiaprofenic acid was investigated on these CSPs. A mobile phase system of acetonitrile–methanol–water (16:4:0.5, v/v/v) was used. The spots were detected with iodine vapours and the detection limits were found to range between 0.25 and 0.5 µg/mL for all racemic compounds investigated. The effect of temperature, pH and concentration of the impregnating chiral selectors on resolution has been studied. Copyright © 2003 John Wiley & Sons, Ltd.
Peter Bukovec - One of the best experts on this subject based on the ideXlab platform.
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Decomposition kinetics of β-cyclodextrin and inclusion complex of β-cyclodextrin with Ibuproxam, 2-(4-isobutylphenyl)propiohydroxamic acid
Thermochimica Acta, 1991Co-Authors: A. Demšar, N. Bukovec, Peter BukovecAbstract:Abstract The kinetics of the thermal decomposition of β-cyclodextrin and of the inclusion complex of β-cyclodextrin with Ibuproxam have been studied by isothermal thermogravimetry between 250 and 275°C. The isothermal curves of β-cyclodextrin and the inclusion complex up to mass losses of 58.1% and 62.0% respectively have been used in the kinetic calculations. The first half of the mass loss obeys nucleation mechanism A2 and the second half obeys a first order F1 mechanism. Activation energies have been calculated.
Paola Mura - One of the best experts on this subject based on the ideXlab platform.
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Characterization of Ibuproxam binary and ternary dispersions with hydrophilic carriers.
Drug development and industrial pharmacy, 2004Co-Authors: Marzia Cirri, Paola Mura, Antonio M. Rabasco, Juan M. Gines, J. R. Moyano, M.l. González-rodríguezAbstract:This work investigates the possibility of increasing the dissolution properties of Ibuproxam (a poorly water‐soluble anti‐inflammatory drug) using hydrophilic carriers such as polyvinylpyrrolidone (PVP), polyethylene glycol (PEG), or urea, alone or in combination. Phase‐solubility studies showed that the carrier solubilizing power was in the order PEG > PVP > urea and evidenced a synergistic effect in drug solubility improvement when using carrier combinations. Binary and ternary systems, at 20/80 or 20/40/40 (w/w) drug/carrier(s) ratios, prepared by coevaporation of their ethanolic solutions or by cogrinding physical mixtures in a high‐energy vibrational micromill, were characterized by differential scanning calorimetry (DSC), hot stage microscopy (HSM), and scanning electron microscopy (SEM) analyses. The results of dissolution tests (USP paddle method), in terms of Dissolution Efficiency, indicated that ternary systems were up to 35% more effective than the corresponding binary preparations and coevapo...
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Computer-aided molecular modeling techniques for predicting the stability of drug–cyclodextrin inclusion complexes in aqueous solutions
Chemical Physics Letters, 2002Co-Authors: M T Faucci, Fabrizio Melani, Paola MuraAbstract:Molecular modeling was used to investigate factors influencing complex formation between cyclodextrins and guest molecules and predict their stability through a theoretical model based on the search for a correlation between experimental stability constants (Ks) and some theoretical parameters describing complexation (docking energy, host– guest contact surfaces, intermolecular interaction fields) calculated from complex structures at a minimum conformational energy, obtained through stochastic methods based on molecular dynamic simulations. Naproxen, ibuprofen, ketoprofen and Ibuproxam were used as model drug molecules. Multiple Regression Analysis allowed identification of the significant factors for the complex stability. A mathematical model (r ¼ 0:897) related log Ks with complex docking energy and lipophilic molecular fields of cyclodextrin and drug. 2002 Elsevier Science B.V. All rights reserved.
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Comparative study of Ibuproxam complexation with amorphous β-cyclodextrin derivatives in solution and in the solid state
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 2002Co-Authors: Paola Mura, Naima Zerrouk, M.teresa Faucci, Francesca Maestrelli, Chantal ChemtobAbstract:Abstract The complexing, solubilizing and amorphizing abilities toward Ibuproxam (a poorly water-soluble anti-inflammatory agent) of some randomly substituted amorphous β-cyclodextrin derivatives (i.e. methyl- (MeβCd), hydroxyethyl- (HEβCd), and hydroxypropyl- (HPβCd) β-cyclodextrins) were investigated and compared with those of the parent β-cyclodextrin. Equimolar drug–cyclodextrin solid systems were prepared by blending, cogrinding, coevaporation, and colyophilization. Drug–carrier interactions were studied in both the liquid and solid state by phase solubility analysis, supported by molecular modelling, differential scanning calorimetry, X-ray powder diffractometry, Fourier transform infrared spectroscopy and scanning electron microscopy. All the βCd derivatives showed greater solubilizing efficacies toward Ibuproxam than the parent one, due to their higher water solubility. On the contrary, a clear reduction of complexing ability was observed, indicative of some steric interferences to drug inclusion due to the presence of substituents, as confirmed by molecular modelling studies. However, this negative effect was not reflected in the dissolution behaviour (evaluated according to the dispersed amount method) of their solid binary systems, probably thanks to the greater amorphizing properties shown (DSC and X-ray analyses) by βCd derivatives. In fact their dissolution efficiencies were not significantly different (MeβCd) or only slightly lower (HEβCd and HPβCd) than those of the corresponding products with β-cyclodextrin. Colyophilized products were in all cases the most effective, followed by coground and coevaporated systems, whose dissolution efficiencies were over four times higher than the corresponding physical mixtures and about 15 times higher than the pure drug.
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Effects of the Host Cavity Size and the Preparation Method on the Physicochemical Properties of Ibuproxam-Cyclodextrin Systems
Drug development and industrial pharmacy, 1999Co-Authors: Paola Mura, Antonio M. Rabasco, J. R. Moyano, E. Adragna, J. I. Pérez-martínez, M. J. Arias, Juan M. GinesAbstract:The effect of cyclodextrin (Cd) complexation on Ibuproxam (IBUX) dissolution properties was studied by evaluating both the influence of Cd cavity size and the preparation method used for obtaining solid inclusion complexes. Binary systems of IBUX with natural Cds, prepared using different techniques (kneading, sealed-heating, spray-drying), were studied by differential scanning calorimetry (DSC), hot-stage microscopy (HSM), Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), and their dissolution behavior was evaluated according to the dispersed amount method. The nature and the dissolution performance of the end product appeared to be related to both steric factors of host molecule and preparation method of the solid system. The αCd cavity size was less suitable for accommodating the IBUX molecule, whereas spray-drying and sealed-heating methods led to a true inclusion complex of IBUX in the βCd and γCd cavity. In contrast, the kneading method did not lead in any case to a...