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Article: Thermal characterization of some polymorph solvates of the anti-inflammatory/anti-cancer sulindac

Cavallari, Cristina / Adamo Fini / Fabrizio Tarterini

Thermochimica acta. 2016 June 10, v. 633

2016

Abstract: Solvates of sulindac were obtained by crystallization from acetone, chloroform, dichloromethane and tetrahydrofuran, but not from water, methanol, ethanol and propanols, acetonitrile and ethyl acetate and were studied by thermal (differential scanning ... ...

Abstract	Solvates of sulindac were obtained by crystallization from acetone, chloroform, dichloromethane and tetrahydrofuran, but not from water, methanol, ethanol and propanols, acetonitrile and ethyl acetate and were studied by thermal (differential scanning calorimetry—DSC, thermogravimetry—TGA and thermomicroscopy—HSM) and spectroscopic (micro-Raman, SEM, X-EDS) analysis.It emerged from the thermal analysis that the samples thus obtained are not simple solvates or pseudo-polymorphs, but rather polymorph solvates, where the new form could be evidenced only after desolvation in controlled conditions, since the desolvation and polymorph transition processes occur together and in the thermogram the endotherms overlap. Desolvation, that is accompanied by decoloration of the sample from orange to yellow, enabled calculation of the solvate stoichiometry by the TGA parameters. The polymorph obtained from desolvation of the acetone solvate displays different thermal parameters from those obtained with chloroform, dichloromethane and tetrahydrofuran solvates. According to the solvents employed for crystallization, these thermal events leave sulindac in the form I or both I and II, outlining the very complex nature of the solid state of this drug. A new unsolvated polymorph form was directly obtained applying the technique of the quasi emulsion solvent diffusion (QESD). These results could open new perspectives in the use of the anti-inflammatory/anti-cancer sulindac in terms of formulation and mode of delivery and release.
Keywords	acetone ; acetonitrile ; chloroform ; crystallization ; decolorization ; drugs ; emulsions ; endothermy ; ethanol ; ethyl acetate ; methanol ; methylene chloride ; propanols ; scanning electron microscopy ; solvents ; spectroscopy ; stoichiometry ; tetrahydrofuran ; thermal analysis ; thermal properties
Language	English
Dates of publication	2016-0610
Size	p. 129-139.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	1500974-9
ISSN	0040-6031
ISSN	0040-6031
DOI	10.1016/j.tca.2016.01.006
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: A Cationic Nanomicellar Complex of the Quaternary Amphiphilic Amine RC16+ with Fenretinide as a New Multitasking System for Antitumor Therapy.

Orienti, Isabella / Cripe, Timothy P / Currier, Mark A / Cavallari, Cristina / Teti, Gabriella / Falconi, Mirella

Current drug delivery

2019 Volume 16, Issue 9, Page(s) 807–817

Abstract: Objectives: This study investigated the antitumor effect of a new nanomicellar complex obtained by combining the antitumor agent fenretinide with a quaternary amphiphilic amine RC16+ also endowed with antitumor activity.: Methods: The complex (Fen- ... ...

Abstract	Objectives: This study investigated the antitumor effect of a new nanomicellar complex obtained by combining the antitumor agent fenretinide with a quaternary amphiphilic amine RC16+ also endowed with antitumor activity. Methods: The complex (Fen-RC16+) strongly improved the aqueous solubility of fenretinide (from 1,71 ± 0.08 µg/ml, pure fenretinide to 1500 ± 164 µg /ml, Fen-RC16+ complex) and provided a cytotoxic effect on SH-SY5Y neuroblastoma cell lines resulting from the intrinsic activity of both the complex components. Moreover, the mean size of the nanomicellar complex (ranging from 20 ± 1.97 nm to 40 ± 3.05 nm) was suitable for accumulation to the tumor site by the enhanced permeability and retention effect and the positive charge provided by the quaternary RC16+ induced adsorption of the complex on the tumor cell surface improving the intracellular concentration of fenretinide. Results: All these characteristics made the Fen-RC16+ complex a multitasking system for antitumor therapy. Conclusion: Indeed its in vivo activity, evaluated on SH-SY5Y xenografts, was strong, and the tumor growth did not resume after the treatment withdrawal.
MeSH term(s)	Animals ; Antineoplastic Agents/administration & dosage ; Antineoplastic Agents/chemistry ; Cell Line, Tumor ; Cell Survival/drug effects ; Drug Delivery Systems ; Drug Liberation ; Female ; Fenretinide/administration & dosage ; Fenretinide/chemistry ; Humans ; Mice, Nude ; Micelles ; Nanostructures/administration & dosage ; Neoplasms/drug therapy ; Quaternary Ammonium Compounds/administration & dosage ; Quaternary Ammonium Compounds/chemistry
Chemical Substances	Antineoplastic Agents ; Micelles ; Quaternary Ammonium Compounds ; Fenretinide (187EJ7QEXL)
Language	English
Publishing date	2019-10-02
Publishing country	United Arab Emirates
Document type	Journal Article
ZDB-ID	2185284-4
ISSN	1875-5704 ; 1567-2018
ISSN (online)	1875-5704
ISSN	1567-2018
DOI	10.2174/1567201816666191002100745
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Article ; Online: Cromolyn-crosslinked chitosan nanoparticles for the treatment of allergic rhinitis.

Abruzzo, Angela / Cerchiara, Teresa / Bigucci, Federica / Zuccheri, Giampaolo / Cavallari, Cristina / Saladini, Bruno / Luppi, Barbara

European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences

2019 Volume 131, Page(s) 136–145

Abstract: The aim of this work was to prepare new mucoadhesive nasal decongestant nanoparticles obtained by direct crosslinking between the cationic polymer chitosan and the anionic drug cromolyn. Different chitosan/cromolyn molar ratios were used in order to ... ...

Abstract	The aim of this work was to prepare new mucoadhesive nasal decongestant nanoparticles obtained by direct crosslinking between the cationic polymer chitosan and the anionic drug cromolyn. Different chitosan/cromolyn molar ratios were used in order to obtain nanoparticles of suitable size, encapsulation efficiency/drug loading and mucoadhesion. Moreover, the ability of the nanoparticles to deliver cromolyn into and through the nasal mucosa was evaluated. The obtained positively charged nanoparticles, sized 180-400 nm, showed interesting properties in terms of yield, mucoadhesion, encapsulation efficiency and drug loading. Release and permeation/penetration data indicated the ability of the nanoparticles to retain a high amount of cromolyn inside the mucosa, which is rich in mast cells. These findings suggest developing decongestant nanoparticles for potential treatment of allergic rhinitis.
MeSH term(s)	Adhesiveness ; Animals ; Anti-Allergic Agents/administration & dosage ; Anti-Allergic Agents/chemistry ; Chitosan/administration & dosage ; Chitosan/chemistry ; Cromolyn Sodium/administration & dosage ; Cromolyn Sodium/chemistry ; Drug Liberation ; Nanoparticles/administration & dosage ; Nanoparticles/chemistry ; Nasal Mucosa/metabolism ; Permeability ; Rhinitis, Allergic/drug therapy ; Sheep
Chemical Substances	Anti-Allergic Agents ; Chitosan (9012-76-4) ; Cromolyn Sodium (Q2WXR1I0PK)
Language	English
Publishing date	2019-02-13
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1154366-8
ISSN	1879-0720 ; 0928-0987
ISSN (online)	1879-0720
ISSN	0928-0987
DOI	10.1016/j.ejps.2019.02.015
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Article ; Online: Ex-vivoand in-vitro assessment of mucoadhesive patches containing the gel-forming polysaccharide psyllium for buccal delivery of chlorhexidine base.

Cavallari, Cristina / Brigidi, Patrizia / Fini, Adamo

International journal of pharmaceutics

2015 Volume 496, Issue 2, Page(s) 593–600

Abstract: The aim of the present study was to evaluate the gel-forming polysaccharide psyllium in the preparation of mucoadhesive patches for the controlled release of chlorhexidine (CHX) to treat pathologies in the oral cavity, using the casting-solvent ... ...

Abstract	The aim of the present study was to evaluate the gel-forming polysaccharide psyllium in the preparation of mucoadhesive patches for the controlled release of chlorhexidine (CHX) to treat pathologies in the oral cavity, using the casting-solvent evaporation technique. A number of different film-forming semi-synthetic polymers, such as sodium carboxymethyl cellulose (SCMC) and hydroxypropylmethyl cellulose (HPMC) were evaluated for comparison. The patch formulations were characterized in terms of drug content, morphology surface, swelling and mucoadhesive properties, microbiology inhibition assay and in vitro release tests. Three ex-vivo testswere carried out using porcine mucosa: an alternative dissolution test using artificial saliva that allows contemporary measurement of dissolution and mucoadhesion, a permeation test through the mucosa and the measurement of mucoadhesion using a Nouy tensile tester, as the maximum force required for the separation of the patch from the mucosa surface. The patches were also examined for determination of the minimum inhibitory concentration in cultures of Escherichia coli and Staphylococcus aureus. All the patches incorporating psyllium were found suitable in terms of external morphology, mucoadhesion and controlled release of the drug: in the presence of psyllium the drug displays prolonged zero-order release related to slower swelling rate of the system.
MeSH term(s)	Adhesives/administration & dosage ; Adhesives/chemistry ; Adhesives/metabolism ; Administration, Buccal ; Animals ; Chlorhexidine/administration & dosage ; Chlorhexidine/chemistry ; Chlorhexidine/metabolism ; Drug Delivery Systems/methods ; Gels/administration & dosage ; Gels/chemistry ; Gels/metabolism ; Mouth Mucosa/drug effects ; Mouth Mucosa/metabolism ; Organ Culture Techniques ; Polysaccharides/administration & dosage ; Polysaccharides/chemistry ; Polysaccharides/metabolism ; Psyllium/administration & dosage ; Psyllium/chemistry ; Psyllium/metabolism ; Swine
Chemical Substances	Adhesives ; Gels ; Polysaccharides ; Psyllium (8063-16-9) ; Chlorhexidine (R4KO0DY52L)
Language	English
Publishing date	2015-12-30
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	428962-6
ISSN	1873-3476 ; 0378-5173
ISSN (online)	1873-3476
ISSN	0378-5173
DOI	10.1016/j.ijpharm.2015.10.077
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Article: Design of olanzapine/lutrol solid dispersions of improved stability and performances.

Cavallari, Cristina / Fini, Adamo / Ceschel, Giancarlo

Pharmaceutics

2013 Volume 5, Issue 4, Page(s) 570–590

Abstract: Eleven solid dispersions containing olanzapine, with carriers of different composition (Lutrol® F68, Lutrol® F127, Gelucire® 44/14), were prepared and examined by thermal (differential scanning calorimetry (DSC); thermomicroscopy (HSM)) and X-ray ... ...

Abstract	Eleven solid dispersions containing olanzapine, with carriers of different composition (Lutrol® F68, Lutrol® F127, Gelucire® 44/14), were prepared and examined by thermal (differential scanning calorimetry (DSC); thermomicroscopy (HSM)) and X-ray diffraction (XRD) analysis, both as fresh or aged (one year) samples. Drug and carriers were preliminarily selected in order to avoid problems related to the aging of the formulation, according to the solubility parameters of carriers and drug. These parameters make it possible to predict the low solubility of olanzapine in the carriers (alone or in mixtures). Systems containing only Lutrol (also in the presence of Transcutol®) contain the drug in the form of particles of reduced size and in a crystalline form. Gelucire® 44/14 apparently increases the amount of olanzapine dissolved in the solid carrier, but this is presumed to be a metastable state, probably related to the heterogeneous nature of the carrier that delays crystallization of the drug. The high hydrophilicity of the carriers proves suitable to an accelerated and quick release of the drug regardless of aging. Differences in the release profiles between Lutrol- and Gelucire-containing systems were interpreted in terms of the formation of polymer micelles by the Lutrols when in aqueous solution.
Language	English
Publishing date	2013-10-25
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics5040570
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Article ; Online: Olanzapine solvates.

Cavallari, Cristina / Santos, Beatriz Pérez-Artacho / Fini, Adamo

Journal of pharmaceutical sciences

2013 Volume 102, Issue 11, Page(s) 4046–4056

Abstract: Olanzapine was crystallized from 12 organic solvents alone or in mixture, by cooling in the freezer, by slow evaporation of the solvent, or by suspending olanzapine powder for some time in the solvent. All the samples thus obtained were examined by ... ...

Abstract	Olanzapine was crystallized from 12 organic solvents alone or in mixture, by cooling in the freezer, by slow evaporation of the solvent, or by suspending olanzapine powder for some time in the solvent. All the samples thus obtained were examined by thermal analysis (differential scanning calorimetry-DSC and thermogravimetry-TG) to certify the formation of a solvate, the presence of polymorph (form 1 or 2) in the desolvated olanzapine, comparing the different profile of the thermograms, and to calculate the stoichiometry of the possible solvate. According to the DSC thermogram, the solvents can be divided into four classes: those that do not form solvates and leave olanzapine form 1 (ethyl acetate, toluene, diethyl ether, and acetone); those that form solvate and leave form 1 of olanzapine after desolvation (methanol, 1- and 2-propanol); those that after desolvation of the solvate show a polymorph transition in the thermogram indicating the presence of form 2 of olanzapine (ethanol); other solvents (tetrahydrofuran, chloroform, acetonitrile) give solvate thermograms, where this last thermal trace is only poorly evident. With few exceptions, each solvent forms solvate both when pure and in mixture (10%, v/v, in ethyl acetate). Methanol monosolvate displays complex thermogram and thermogravimetric desolvation profiles, depending on the crystallization experimental conditions, used to prepare the solvates. Dichloromethane solvate was found by X-ray diffraction analysis to be amorphous and, on heating during DSC analysis, allowed the crystallization of both form 1 and 2, with different weight ratio, according to the experimental conditions of the solvate preparation.
MeSH term(s)	Antiemetics/chemistry ; Antipsychotic Agents/chemistry ; Benzodiazepines/chemistry ; Calorimetry, Differential Scanning ; Crystallization ; Powder Diffraction ; Solubility ; Solvents/chemistry ; Thermogravimetry ; X-Ray Diffraction
Chemical Substances	Antiemetics ; Antipsychotic Agents ; Solvents ; Benzodiazepines (12794-10-4) ; olanzapine (N7U69T4SZR)
Language	English
Publishing date	2013-11
Publishing country	United States
Document type	Journal Article
ZDB-ID	3151-3
ISSN	1520-6017 ; 0022-3549
ISSN (online)	1520-6017
ISSN	0022-3549
DOI	10.1002/jps.23714
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Article ; Online: Mucoadhesive multiparticulate patch for the intrabuccal controlled delivery of lidocaine.

Cavallari, Cristina / Fini, Adamo / Ospitali, Francesca

European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V

2013 Volume 83, Issue 3, Page(s) 405–414

Abstract: The aim of the present study was to prepare and evaluate patches for the controlled release of lidocaine in the oral cavity. Mucoadhesive buccal patches, containing 8 mg/cm(2) lidocaine base, were formulated and developed by solvent casting method ... ...

Abstract	The aim of the present study was to prepare and evaluate patches for the controlled release of lidocaine in the oral cavity. Mucoadhesive buccal patches, containing 8 mg/cm(2) lidocaine base, were formulated and developed by solvent casting method technique, using a number of different bio-adhesive and film-forming semi-synthetic and synthetic polymers (Carbopol, Poloxamer, different type Methocel) and plasticizers (PEG 400, triethyl citrate); the patches were evaluated for bioadhesion, in vitro drug release and permeation using a modified Franz diffusion cell. A lidocaine/Compritol solid dispersion in the form of microspheres, embedded inside the patch, alone or together with free lidocaine, was also examined to prolong the drug release. The effects of the composition were evaluated considering a number of technological parameters and the release of the drug. All the formulations tested offer a variety of drug release mechanisms, obtaining a quick or delayed or prolonged anesthetic local activity with simple changes of the formulation parameters.
MeSH term(s)	Adhesives ; Anesthetics, Local/administration & dosage ; Anesthetics, Local/pharmacokinetics ; Animals ; Calorimetry, Differential Scanning ; Cell Line ; Lidocaine/administration & dosage ; Lidocaine/pharmacokinetics ; Mice ; Microscopy, Electron, Scanning ; Mouth Mucosa ; Particle Size ; Spectrum Analysis, Raman
Chemical Substances	Adhesives ; Anesthetics, Local ; Lidocaine (98PI200987)
Language	English
Publishing date	2013-04
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1065368-5
ISSN	1873-3441 ; 0939-6411
ISSN (online)	1873-3441
ISSN	0939-6411
DOI	10.1016/j.ejpb.2012.10.004
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Article: Diclofenac Salts, VIII. Effect of the Counterions on the Permeation through Porcine Membrane from Aqueous Saturated Solutions.

Fini, Adamo / Bassini, Glenda / Monastero, Annamaria / Cavallari, Cristina

Pharmaceutics

2012 Volume 4, Issue 3, Page(s) 413–429

Abstract: The following bases: monoethylamine (EtA), diethylamine (DEtA), triethylamine (TEtA), monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), pyrrolidine (Py), piperidine (Pp), morpholine (M), piperazine (Pz) and their N-2-hydroxyethyl (HE) ... ...

Abstract	The following bases: monoethylamine (EtA), diethylamine (DEtA), triethylamine (TEtA), monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), pyrrolidine (Py), piperidine (Pp), morpholine (M), piperazine (Pz) and their N-2-hydroxyethyl (HE) analogs were employed to prepare 14 diclofenac salts. The salts were re-crystallized from water in order to obtain forms that are stable in the presence of water. Vertical Franz-type cells with a diffusional surface area of 9.62 cm2 were used to study the permeation of these diclofenac salts from their saturated solutions through an internal pig ear membrane. The receptor compartments of the cells contained 100 mL of phosphate buffer (pH 7.4); a saturated solution (5 mL) of each salt was placed in the donor compartment, thermostated at 37 °C. Aliquots were withdrawn at predetermined time intervals over 8 h and then immediately analyzed by HPLC. Fluxes were determined by plotting the permeated amount, normalized for the membrane surface area versus time. Permeation coefficients were obtained dividing the flux values J by the concentration of the releasing phase-that is, water solubility of each salt. Experimental results show that fluxes could be measured when diclofenac salts with aliphatic amines are released from a saturated aqueous solution. Different chemical species (acid, anion, ion pairs) contribute to permeation of the anti-inflammatory agent even though ion-pairs could be hypothesized to operate to a greater extent. Permeation coefficients were found higher when the counterion contains a ring; while hydroxy groups alone do not appear to play an important role, the ring could sustain permeation, disrupting the organized domains of the membrane.
Language	English
Publishing date	2012-09-12
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics4030413
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Article ; Online: Image analysis of lutrol/gelucire/olanzapine microspheres prepared by ultrasound-assisted spray congealing.

Cavallari, Cristina / Gonzalez-Rodriguez, Marisa / Tarterini, Fabrizio / Fini, Adamo

European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V

2014 Volume 88, Issue 3, Page(s) 909–918

Abstract: Nine systems were prepared containing Gelucire 50/13 and various amounts (9-18-36-45% w/w) of Lutrol F68 and F127 in the presence and in the absence of 10% w/w of olanzapine and formulated as a solid dispersion in the form of microspheres by ultrasound ( ... ...

Abstract	Nine systems were prepared containing Gelucire 50/13 and various amounts (9-18-36-45% w/w) of Lutrol F68 and F127 in the presence and in the absence of 10% w/w of olanzapine and formulated as a solid dispersion in the form of microspheres by ultrasound (US)-assisted spray congealing. Thermal analysis, using differential scanning calorimetry (DSC) and thermomicroscopy (HSM), suggested the presence of particles of reduced size of olanzapine precipitated inside the microspheres. The microspheres were also studied by means of electron microscopy (SEM) for their shape and aspect, by some image analysis parameters (fractal dimension) and using Energy-dispersive X-ray (X-EDS) and micro-Raman spectroscopy to qualitatively evaluate the composition of different points of the surface. The surface of the microspheres displayed a non-homogeneous distribution of the drug by the presence of wart-like protuberances, whose number increases as the Lutrol content of the systems increases. The same systems in the absence of US, obtained after cooling the molten mixtures, lack these structures and only a very few of them can be found. The blooming of the surface was hypothesized as related to crystallization or phase de-mixing or lipid component diffusion of the carrier mixture inside the cooling mass subjected to ultrasound vibration. Ultrasounds accelerate the physical changes concerning carriers and drug, outlining the importance of ultrasound to achieve stability for formulations of this type. The microspheres de-aggregate on contact with the dissolution medium and release the drug with a bimodal mode according to the Lutrol content.
MeSH term(s)	Benzodiazepines/analysis ; Benzodiazepines/chemistry ; Calorimetry, Differential Scanning/methods ; Chemistry, Pharmaceutical/methods ; Fats/analysis ; Fats/chemistry ; High-Energy Shock Waves ; Microspheres ; Oils/analysis ; Oils/chemistry ; Polyethylene Glycols/analysis ; Polyethylene Glycols/chemistry ; Spectrum Analysis, Raman/methods
Chemical Substances	Fats ; Lutrol ; Oils ; Gelucire 50-13 (121548-05-8) ; Benzodiazepines (12794-10-4) ; Polyethylene Glycols (30IQX730WE) ; olanzapine (N7U69T4SZR)
Language	English
Publishing date	2014-11
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1065368-5
ISSN	1873-3441 ; 0939-6411
ISSN (online)	1873-3441
ISSN	0939-6411
DOI	10.1016/j.ejpb.2014.08.014
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Article: Diclofenac Salts. V. Examples of Polymorphism among Diclofenac Salts with Alkyl-hydroxy Amines Studied by DSC and HSM.

Fini, Adamo / Cavallari, Cristina / Ospitali, Francesca

Pharmaceutics

2010 Volume 2, Issue 2, Page(s) 136–158

Abstract: Nine diclofenac salts prepared with alkyl-hydroxy amines were analyzed for their properties to form polymorphs by DSC and HSM techniques. Thermograms of the forms prepared from water or acetone are different in most cases, suggesting frequent examples of ...

Abstract	Nine diclofenac salts prepared with alkyl-hydroxy amines were analyzed for their properties to form polymorphs by DSC and HSM techniques. Thermograms of the forms prepared from water or acetone are different in most cases, suggesting frequent examples of polymorphism among these salts. Polymorph transition can be better highlighted when analysis is carried out by thermo-microscopy, which in most cases made it possible to observe the processes of melting of the metastable form and re-crystallization of the stable one. Solubility values were qualitatively related to the crystal structure of the salts and the molecular structure of the cation.
Language	English
Publishing date	2010-04-27
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics2020136
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