An examination of the thermodynamics of fusion, vaporization, and sublimation of (R,S)- and (R)-flurbiprofen by correlation gas chromatography.

Abstract:

:The vaporization, fusion, and sublimation enthalpies of (R,S)- and (R)-flurbiprofen at T = 298.15 K are reported and compared with literature values when available. Correlation gas chromatography experiments were first performed to identify appropriate standards that could be used for materials containing a single fluorine substituent. Subsequent correlations resulted in a vaporization enthalpy for (R,S)-flurbiprofen and (R)-flurbiprofen, ΔH(vap) (298.15 K), of (127.5 ± 5.5) and (127.4 ± 4.7) kJ mol, respectively. Fusion enthalpies, ΔH(fus) (387 K), of (28.2 ± and, ΔH(fus) (381 K), (22.8 ± kJ mol(-1) were also measured by differential scanning calorimetry for the racemic and chiral forms of flurbiprofen. Adjusted to T = 298.15 K and combined with the vaporization enthalpy resulted in sublimation enthalpies, ΔH(sub) (298.15 K), of (155.6 ± 5.8) and (145.1 ± 5.7) kJ mol(-1) for (R,S)- and (R)-flurbiprofen, respectively. The fusion enthalpy measured for the racemic form was in excellent agreement with the literature value, while the sublimation enthalpy varies substantially from previous work. Two weak solid-solid phase transitions were also observed for (R)-flurbiprofen at T = 353.9 K (0.30 ± 0.1) and 363.2 K (0.21 ± 0.03) kJ · mol(-1).

journal_name

J Pharm Sci

authors

Umnahanant P,Hasty D,Chickos J

doi

10.1002/jps.23094

subject

Has Abstract

pub_date

2012-06-01 00:00:00

pages

2045-54

issue

6

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)31563-X

journal_volume

101

pub_type

杂志文章
  • Biodegradable microspheres. X: Some properties of polyacryl starch microparticles prepared from acrylic acid-esterified starch.

    abstract::Acrylic acid-esterified starch was produced by reacting starch with acrylic acid chloride. This reaction was rapid and easy to control. Introduction of acrylic groups into starch reduced the enzymatic degradability of starch (e.g., with 12 acrylic groups/100 glucose residues, approximately 75% of the degradation produ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600761219

    authors: Laakso T,Sjöholm I

    更新日期:1987-12-01 00:00:00

  • Optimizing a Novel Au-Grafted Lipid Nanoparticle Through Chelation Chemistry for High Photothermal Biologic Activity.

    abstract::Gold nanoparticles through nucleation of Au clusters have been extensively studied. However, due to low potency, prolonged tissue retention, and irreversible accumulation, the safety considerations have limited their therapeutic and diagnostic applications. Novel gold nanostructures with retained physical properties a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.02.010

    authors: Gao Y,Mu Q,Zhu L,Li Z,Ho RJY

    更新日期:2020-05-01 00:00:00

  • Drug diffusion through cystic fibrotic mucus: steady-state permeation, rheologic properties, and glycoprotein morphology.

    abstract::One manifestation of cystic fibrosis (CF) is the presence of a viscid mucus secretion in the lungs. The clearance of this mucus is significantly slower than in "normals" due to uncoordinated beating of the cilia and the increased viscosity of the mucus. In these studies, the permeabilities of p-aminosalicylic acid, is...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js950381s

    authors: Bhat PG,Flanagan DR,Donovan MD

    更新日期:1996-06-01 00:00:00

  • Kinetics and mechanism of degradation of cefotaxime sodium in aqueous solution.

    abstract::The degradation kinetics and mechanism of a potent new cephalosporin, cefotaxime sodium, in aqueous solution were investigated at pH 0-10 at 25 degrees and an ionic strength of 0.5. The degradation rates were determined by high-pressure liquid chromatography and were observed to follow pseudo first-order kinetics with...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720114

    authors: Berge SM,Henderson NL,Frank MJ

    更新日期:1983-01-01 00:00:00

  • Oil-frozen W₁/O/W₂ double emulsions for dermal biomacromolecular delivery containing ethanol as chemical penetration enhancer.

    abstract::Oil-frozen water-in-oil-in-water (W₁/O/W₂) double emulsions (DE) containing ethanol up to 40% (w/v) in the external aqueous W₂ phase exhibited external coalescence upon thawing of the oil phase, releasing up to 85% of the encapsulated protein of the internal aqueous phase. These emulsions were studied in vitro as pote...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22362

    authors: Jaimes-Lizcano YA,Lawson LB,Papadopoulos KD

    更新日期:2011-04-01 00:00:00

  • Difference spectrophotometric determination of p-hydroxybenzoic acid in presence of its esters.

    abstract::A difference spectrophotometric analytical method was developed for the selective determination of p-hydroxybenzoic acid in the presence of its alkyl esters without prior separation. Based on the spectral shift to a shorter wavelength accompanyint carboxyl dissociation, the procedure measures as little as 2% of this a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670629

    authors: Fink DW,Fink HC,Tolan JW,Blodinger J

    更新日期:1978-06-01 00:00:00

  • Low-density microparticles with petaloid surface structure for pulmonary drug delivery.

    abstract::The morphology of spray-dried particles composed of psicose and hydroxypropyl methylcellulose was modified by adding ammonium bicarbonate (ABC) to the solution. The surface structure of the particles was altered by immediate transformation of ABC to gaseous components during the spray drying. As a result, low-density ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23899

    authors: Kawakami K,Hasegawa Y,Zhang S,Yoshihashi Y,Yonemochi E,Terada K

    更新日期:2014-04-01 00:00:00

  • In vitro and in vivo evaluation of a sulfenamide prodrug of basic metformin.

    abstract::In the present study, a previously described sulfenamide prodrug of a basic antidiabetic drug, metformin, was evaluated further. This sulfenamide prodrug was designed to improve the permeability and consequently the oral absorption and bioavailability (F) of the highly water-soluble metformin. Bioactivation of the pro...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23221

    authors: Huttunen KM,Leppänen J,Vepsäläinen J,Sirviö J,Laine K,Rautio J

    更新日期:2012-08-01 00:00:00

  • Antiradiation compounds XV: condensations of carbon disulfide with amino, chloro, cyanomethyl, and sulfonamido heterocycles.

    abstract::Condensations of carbon disulfide were carried out with amino, chloro, and diamino heterocycles to give condensed ring thiazoline-2-thiones and imidazoline-2-thiones, with cyanomethyl heterocycles to give dithio acid derivatives, and with heterocyclic sulfonamides to give sulfonyldithiocarbamates. Of several examples ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600640823

    authors: Foye WO,Kauffman JM,Lanzillo JJ,LaSala EF

    更新日期:1975-08-01 00:00:00

  • Porous resins as a cavitation enhancer for low-frequency sonophoresis.

    abstract::The application of low-frequency ultrasound enhances drug transport through the skin, a phenomenon referred to as low-frequency sonophoresis. This enhancement is mediated through cavitation, the formation and collapse of gaseous bubbles. We hypothesized that the efficacy of low-frequency sonophoresis can be significan...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10080

    authors: Terahara T,Mitragotri S,Langer R

    更新日期:2002-03-01 00:00:00

  • Differences in Food Effects for 2 Weak Bases With Similar BCS Drug-Related Properties: What Is Happening in the Intestinal Lumen?

    abstract::Ketoconazole and posaconazole are both Biopharmaceutics Classification System class 2 drugs (highly permeable, poorly soluble), are structurally similar, and are administered at the same doses. Nevertheless, the duodenal concentration profile and the magnitude of the positive food effect observed for these 2 drugs are...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2015.11.033

    authors: Cristofoletti R,Patel N,Dressman JB

    更新日期:2016-09-01 00:00:00

  • A novel class of cardiotonic agents: synthesis and biological evaluation of pyridazino[4,5-b]indoles with cyclic AMP phosphodiesterases inhibiting properties.

    abstract::Some fused pyridazino[4,5-b]indoles (7) were synthesized. These new compounds present a planar topography and some resemblance to carbazeram, imadozan, and other pyridazino agents with cardiotonic activity. These compounds also possess a complementary effect as inhibitors of platelet aggregation. 6-(3,5-Dimethylpyrazo...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600820519

    authors: Monge A,Aldana I,Losa MJ,Font M,Castiella E,Frechilla D,Cenarruzabeitia E,Martinez de Irujo JJ,Lopez-Unzu J,Alberdi E

    更新日期:1993-05-01 00:00:00

  • Isomeric benzoylpyrroleacetic acids: some structural aspects for aldose reductase inhibitory and anti-inflammatory activities.

    abstract::A number of isomeric benzoylpyrroleacetic acids (1-6) were prepared and tested in vitro for rat lenses aldose reductase activity. These pyrrole derivatives are structurally related to the acidic nonsteroidal anti-inflammatory drugs. Therefore, their anti-inflammatory properties were also evaluated in the carrageenan-i...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600840119

    authors: Demopoulos VJ,Rekka E

    更新日期:1995-01-01 00:00:00

  • Estimation of the effect of NaCl on the solubility of organic compounds in aqueous solutions.

    abstract::The Setschenow constant, K(salt), of a nonelectrolyte in a NaCl solution is shown to be related to the logarithm of its octanol-water partition coefficient, log K(ow), determined by K(salt) = A log K(ow) + B, where K(ow) is the octanol-water partition coefficient of the solute and the coefficients A and B are constant...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/1520-6017(200012)89:12<1620::aid-jps13>3.0

    authors: Ni N,El-Sayed MM,Sanghvi T,Yalkowsky SH

    更新日期:2000-12-01 00:00:00

  • Pharmacokinetics and tissue distribution after intravenous administration of a single dose of amphotericin B cochleates, a new lipid-based delivery system.

    abstract::Model independent pharmacokinetic analysis of intravenous (iv) amphotericin B cochleates (CAMB), a new lipid-based drug delivery system, in mice (0.625 mg/kg) shows a two-phase disposition profile in blood [area under the curve of concentration versus time from time zero to infinity (AUC(0-infinity)) = 1.01 microg. h/...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10173

    authors: Segarra I,Movshin DA,Zarif L

    更新日期:2002-08-01 00:00:00

  • Protein nanoparticles for intracellular delivery of therapeutic enzymes.

    abstract::The use of enzymes as therapeutics is very promising because of their catalytic activity and specificity. However, intracellular delivery of active enzymes is challenging due to their low stability and large size. The production of protein-enzyme nanoparticles was investigated with the goal of developing a protein car...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23974

    authors: Estrada LH,Chu S,Champion JA

    更新日期:2014-06-01 00:00:00

  • Quantitative dexamethasone and dexamethasone sodium phosphate determinations in pharmaceutical dosage forms by high-pressure liquid chromatography.

    abstract::A high-pressure liquid chromatographic procedure for quantitative dexamethasone and dexamethasone sodium phosphate determinations in all types of commercially available pharmaceutical dosage forms was developed. The method also separates dexamethasone from its phosphate salt and separates dexamethasone or its salt fro...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680743

    authors: Gupta VD

    更新日期:1979-07-01 00:00:00

  • Simultaneously manufactured nano-in-micro (SIMANIM) particles for dry-powder modified-release delivery of antibodies.

    abstract::Simultaneously Manufactured Nano-In-Micro (SIMANIM) particles for the pulmonary delivery of antibodies have been prepared by the spray-drying of a double-emulsion containing human IgG (as a model antibody), lactose, poly(lactide-co-glycolide) (PLGA) and dipalmitoylphosphatidylcholine (DPPC). The one-step drying proces...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21673

    authors: Kaye RS,Purewal TS,Alpar HO

    更新日期:2009-11-01 00:00:00

  • Steady-state pharmacokinetics of haloperidol and reduced haloperidol in schizophrenic patients: analysis of factors determining their concentrations in hair.

    abstract::Profiles of the steady-state concentrations of haloperidol (HL) and its major metabolite, reduced haloperidol (RHL), in plasma versus time were determined in 10 Japanese patients whose schizophrenic symptoms were clinically controlled by fixed, oral maintenance doses (4-30 mg/day, three times a day) for greater than 4...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600811010

    authors: Uematsu T,Matsuno H,Sato H,Hirayama H,Hasegawa K,Nakashima M

    更新日期:1992-10-01 00:00:00

  • Determination of sodium fusidate and fusidic acid in dosage forms by high-performance liquid chromatography and a microbiological method.

    abstract::A new High-performance liquid chromatographic (HPLC) method for the assay of sodium fusidate (I) or fusidic acid in dosage forms was developed and compared to a microbiological assay. A linear relationship was obtained between absolute peak area and amount of I(r = 0.99+) in the 50-1000-microgram/ml range. In the micr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600711130

    authors: Hikal AH,Shibl A,El-Hoofy S

    更新日期:1982-11-01 00:00:00

  • Intravenous dosing conditions may affect systemic clearance for highly lipophilic drugs: implications for lymphatic transport and absolute bioavailability studies.

    abstract::The clearance (Cl) and volume of distribution (V(ss)) of a lipophilic, lymphatically transported drug, halofantrine (Hf) have been evaluated after intravenous delivery to the systemic circulation in ex vivo lymph and plasma, and compared with the data obtained after administration of a lipid-based emulsion and a lipid...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23211

    authors: Caliph SM,Trevaskis NL,Charman WN,Porter CJ

    更新日期:2012-09-01 00:00:00

  • Freeze drying of L-arginine/sucrose-based protein formulations, part I: influence of formulation and arginine counter ion on the critical formulation temperature, product performance and protein stability.

    abstract::The objective of this study was to investigate product performance of freeze dried l-arginine/sucrose-based formulations under variation of excipient weight ratios, l-arginine counter ions and formulation pH as a matrix to stabilize a therapeutic monoclonal antibody (MAb) during freeze drying and shelf life. Protein a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24501

    authors: Stärtzel P,Gieseler H,Gieseler M,Abdul-Fattah AM,Adler M,Mahler HC,Goldbach P

    更新日期:2015-07-01 00:00:00

  • Stereoselective disposition of talinolol in man.

    abstract::The disposition of the beta-blocking drug talinolol is controlled by P-glycoprotein in man. Because talinolol is marketed as a racemate, we reevaluated the serum-concentration time profiles of talinolol of a previously published study with single intravenous (30 mg) and repeated oral talinolol (100 mg for 14 days) bef...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10054

    authors: Zschiesche M,Lemma GL,Klebingat KJ,Franke G,Terhaag B,Hoffmann A,Gramatté T,Kroemer HK,Siegmund W

    更新日期:2002-02-01 00:00:00

  • Plasma concentrations and bioavailability of clofibric acid from its calcium salt in humans.

    abstract::The bioavailability of clofibric acid from formulations containing calcium clofibrate along and mixed with calcium carbonate (1:1 w/w) was compared to that from a standard clofibrate formulation in a crossover study in 12 human subjects. The 95% confidence intervals of bioavailability differences were such that they ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600661138

    authors: Taylor T,Chasseaud LF

    更新日期:1977-11-01 00:00:00

  • Unified physicochemical property estimation relationships (UPPER).

    abstract::The knowledge of physicochemical properties of organic compounds becomes increasingly important in pharmaceutical sciences, chemical engineering, and other fields. In this study, we developed UPPER (Unified Physicochemical Property Estimation Relationships), a comprehensive model for the estimation of 20 physicochemic...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24033

    authors: Lian B,Yalkowsky SH

    更新日期:2014-09-01 00:00:00

  • Stabilization of proteins by recombinant human gelatins.

    abstract::Porcine gelatins have been widely used as stabilizers of macromolecular based pharmaceuticals but the mechanism by which they stabilize has not been precisely established. Their variability and immunogenicity, however, make them less than ideal excipients. In this work, we take advantage of the availability of recombi...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20980

    authors: Thyagarajapuram N,Olsen D,Middaugh CR

    更新日期:2007-12-01 00:00:00

  • A novel calmodulin antagonist O-(4-ethoxyl-butyl)-berbamine overcomes multidrug resistance in drug-resistant MCF-7/ADR breast carcinoma cells.

    abstract::Multidrug resistance (MDR) mediated by the overexpression of the drug efflux protein P-glycoprotein is one of the major obstacles to successful cancer chemotherapy. The development of safe and effective MDR-reversing agents is an important approach to addressing this problem clinically. In this study, we evaluated the...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22082

    authors: Liu R,Zhang Y,Chen Y,Qi J,Ren S,Xushi MY,Yang C,Zhu H,Xiong D

    更新日期:2010-07-01 00:00:00

  • PEGylation as a tool for the biomedical engineering of surface modified microparticles.

    abstract::Microparticles are of considerable interest for drug delivery, vaccination and diagnostic imaging. In order to obtain microparticles with long circulation times, or to provide the prerequisite for tissue specific targeting through decoration with suitable ligands, their surfaces need to be modified such that they beco...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1002/jps.21350

    authors: Wattendorf U,Merkle HP

    更新日期:2008-11-01 00:00:00

  • Computer modeling of adsorption on an activated charcoal surface.

    abstract::The molecular modeling program SYBYL was used to simulate the adsorption of various barbiturates by an activated charcoal surface. The compounds barbituric acid (BA), barbital (B), phenobarbital (PB), mephobarbital (M), and primidone (Pr) were modeled, and their structures were energetically minimized. These structure...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600831214

    authors: Wurster DE,Kolling WM,Knosp BM

    更新日期:1994-12-01 00:00:00

  • Design and optimization of self-nanoemulsifying delivery system to enhance quercetin hepatoprotective activity in paracetamol-induced hepatotoxicity.

    abstract::The present study aimed to develop optimized quercetin (QT)-loaded self-nanoemulsifying drug delivery system (SNEDDS) that offers protective effect against liver damage. Solubility study of QT in different oils, surfactants, and cosurfactants was performed. Ternary phase mixtures of the selected components were constr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23834

    authors: Ahmed OA,Badr-Eldin SM,Tawfik MK,Ahmed TA,El-Say KM,Badr JM

    更新日期:2014-02-01 00:00:00