Thermodynamics of the Enantiotropic Pharmaceutical Compound Benzocaine and Solubility in Pure Organic Solvents.

Abstract:

:The thermodynamic relationship between FI and FII of ethyl 4-aminobenzoate (benzocaine) has been investigated. Slurry conversion experiments show that the transition temperature below which FI is stable is located between 302 K-303 K (29 °C-30 °C). The polymorphs FI and FII have been characterised by infrared spectroscopy (IR), Raman spectroscopy, transmission powder X-ray diffraction (XRPD) and differential scanning calorimetry (DSC). The isobaric solid state heat capacities have been measured by DSC. The quantitative thermodynamic stability relationship has been determined in a comprehensive thermodynamic analysis of the calorimetric data. The solubility of both polymorphs has been determined in eight pure organic solvents over the temperature range 278 K-323 K by a gravimetric method. The mole fraction solubility of benzocaine decreases in the order: 1,4-dioxane, acetone, ethyl acetate, chloroform, acetonitrile, methanol, n-butanol and toluene. Comparison with the determined activity of solid benzocaine forms shows that negative deviation from Raoult's law ideality is found in dioxane, acetone and ethyl acetate solutions, and positive deviation in solutions of the other investigated solvents.

journal_name

J Pharm Sci

authors

Cheuk D,Svärd M,Rasmuson ÅC

doi

10.1016/j.xphs.2020.07.022

subject

Has Abstract

pub_date

2020-11-01 00:00:00

pages

3370-3377

issue

11

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(20)30413-5

journal_volume

109

pub_type

杂志文章
  • Electromigration of ions across the skin: determination and prediction of transport numbers.

    abstract::In iontophoresis, an electric field across the skin induces electromigration of exogenously applied and endogenously present ions. The approach can be used to improve dramatically drug delivery by elimination of competing co-ions in the externally applied formulation, as this maximizes the fraction of current carried ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20561

    authors: Mudry B,Guy RH,Delgado-Charro MB

    更新日期:2006-03-01 00:00:00

  • Cerebral kinetics of oxycodone in conscious sheep.

    abstract::Oxycodone is an opioid analgesic that is administered orally or parenterally. The time-course of opioid action is a function of the systemic kinetics of the opioid, and the rate and extent of its entry into the brain and central nervous system. The latter is incompletely understood for oxycodone. Therefore, the cerebr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20632

    authors: Villesen HH,Foster DJ,Upton RN,Somogyi AA,Martinez A,Grant C

    更新日期:2006-08-01 00:00:00

  • Dosage intervals based on mean residence times.

    abstract::It is shown that a suitable dosage interval, tau, can be estimated by a factor times the sum of the mean residence time (MRT) of the central compartment (MRTC) and the MRT of the absorption site (MRTA). This value of tau will provide a ratio, maximum steady-state plasma concentration: minimum steady-state plasma conce...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600760111

    authors: Wagner JG

    更新日期:1987-01-01 00:00:00

  • GI absorption of beta-lactam antibiotics. III: Kinetic evidence for in situ absorption of ionized species of monobasic penicillins and cefazolin from the rat small intestine and structure-absorption rate relationships.

    abstract::Absorption rates of monobasic beta-lactam antibiotics were measured as a function of lumen solution pH between 4 and 9 by utilizing the rat intestinal recirculating method in situ. Between pH 6.5 and 9, the absorption rate constants of ionized antibiotics were almost identical; but, at pH 4, the unionized species were...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680706

    authors: Tsuji A,Miyamoto E,Kubo O,Yamana T

    更新日期:1979-07-01 00:00:00

  • A new approach in the synthesis of immunotoxins: ribosome inactivating protein noncovalently bound to monoclonal antibody.

    abstract::This study describes the synthesis of a new generation of immunotoxins made by a noncovalent interaction between a monoclonal antibody derivatized with a dichlorotriazinic dye and the ribosomal inhibitor protein gelonin. The scheme of preparation has several advantages with respect to the traditional methods, which us...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600830218

    authors: Dosio F,Brusa P,Delprino L,Grosa G,Ceruti M,Cattel L

    更新日期:1994-02-01 00:00:00

  • Relating Protein-Protein Interactions and Aggregation Rates From Low to High Concentrations.

    abstract::At low protein concentrations (c2), non-native protein aggregation rates are known to be sensitive to changes in conformational stability and "weak" or "colloidal" protein-protein interactions. Protein-protein interactions are also known to be strong functions of c2. In the present work, protein-protein interactions a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2016.01.004

    authors: Ghosh R,Calero-Rubio C,Saluja A,Roberts CJ

    更新日期:2016-03-01 00:00:00

  • GLC method for iminodibenzyl and desipramine impurities in imipramine hydrochloride and its formulated products.

    abstract::A GLC method is described for the determination of iminodibenzyl and desipramine impurities in imipramine hydrochloride and its formulated products. These impurities were extracted from an alkaline solution with a mixture of 30% methylene chloride in hexane for chromatography on a 3% OV-17 GLC column. Iminodibenzyl wa...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600710515

    authors: Thompson DW

    更新日期:1982-05-01 00:00:00

  • Hydrazine levels in formulations of hydralazine, isoniazid, and phenelzine over a 2-year period.

    abstract::Hydrazine levels in formulations of hydralazine, isoniazid, and phenelzine have been measured over a 2-year period under ambient conditions and under temperature and humidity stress. Hydralazine tablets are stable under ambient conditions, but the hydrazine level in an injectable formulation increased from 4.5 to 10 m...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720836

    authors: Lovering EG,Matsui F,Curran NM,Robertson DL,Sears RW

    更新日期:1983-08-01 00:00:00

  • Computation of in-house quality control limits for pharmaceutical dosage forms based on product variability.

    abstract::A method for establishing sampling plans for in-house limits that fix both the producer's and consumer's risks is presented for pharmaceutical systems in which both between-batch and within-batch variations are present. Such plans can always be constructed and require more or less sample assays depending on the variab...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720421

    authors: Bolton S

    更新日期:1983-04-01 00:00:00

  • Improvement in solubility and dissolution rate of 1, 2-dithiole-3-thiones upon complexation with beta-cyclodextrin and its hydroxypropyl and sulfobutyl ether-7 derivatives.

    abstract::Inclusion complexes between beta-cyclodextrin derivatives and 1, 2-dithione-3-thiones were studied in aqueous solution and in the solid state. Phase solubility study was used to evaluate the complexation in solution, at 37 degrees C, of three cyclodextrins, i. e., beta-cyclodextrin (betaCD), hydroxypropyl-beta-cyclode...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js990067o

    authors: Dollo G,Le Corre P,Chollet M,Chevanne F,Bertault M,Burgot JL,Le Verge R

    更新日期:1999-09-01 00:00:00

  • 3D Printing of Solid Oral Dosage Forms: Numerous Challenges With Unique Opportunities.

    abstract::Since the FDA approval of Spritam, there has been a growing interest in the application of 3D printing in pharmaceutical science. 3D printing is a method of manufacturing involving the layer-by-layer deposition of materials to create a final product according to a digital model. There are various techniques used to ac...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1016/j.xphs.2020.08.029

    authors: Okafor-Muo OL,Hassanin H,Kayyali R,ElShaer A

    更新日期:2020-12-01 00:00:00

  • Barriers to nonviral gene delivery.

    abstract::The use of various synthetic lipids and polymers to deliver DNA for gene therapy applications has been the subject of intense examination for the last 15 years. Our understanding of the processes involved in the delivery of DNA, although still limited, can be described in terms of specific physical and chemical barrie...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1002/jps.10286

    authors: Wiethoff CM,Middaugh CR

    更新日期:2003-02-01 00:00:00

  • Determination of 17-hydroxycorticosteroids in human urine.

    abstract::A study was undertaken to develop a method that could be used an an indication of the absorption of steroids. It was demonstrated that 17-hydroxycorticosteroids in urine could be quantitatively determined via absorptivity values obtained through the use of standard hydrocortisone-alcohol solutions or standard solution...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600640643

    authors: Feinstein W,Sciarra JJ

    更新日期:1975-06-01 00:00:00

  • Stereospecific assay and stereospecific disposition of racemic carprofen in rats.

    abstract::A procedure was developed for the separation and selective quantitative determination of the (S)(+)- and (R)(-)-enantiomers of the racemic anti-inflammatory drug carprofen as their diastereomeric l-(-)-alpha-methylbenzylamides. These derivatives are obtained in equivalent yields by reacint purified 14C-carprofen from ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600681021

    authors: Kemmerer JM,Rubio FA,McClain RM,Koechlin BA

    更新日期:1979-10-01 00:00:00

  • Experimental evaluation of a model for predicting micellar composition and concentration of monomeric species in bile salt binary mixtures.

    abstract::The critical micellar concentration (cmc) values of some mixed systems containing two bile salts were determined by a maximum pressure bubble method and compared with those derived from a theoretical model developed for nonionic surfactants to assess the applicability of this model to such systems. Some assumptions on...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600840514

    authors: Roda A,Cerré C,Fini A,Sipahi AM,Baraldini M

    更新日期:1995-05-01 00:00:00

  • GLC determination of procainamide in biological fluids.

    abstract::A GLC method for the determination of procainamide in biological fluids is presented. By using a dipropyl analog of procainamide as an internal standard, both compounds can be chromatographed directly, yielding linear calibration curves and a sensitivity that allows quantitative determination of concentrations as low ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600641213

    authors: Simons KJ,Levy RH

    更新日期:1975-12-01 00:00:00

  • Identification of the major degradation products of 4-methoxy-2-(3-phenyl-2-propynyl)phenol formed by exposure to air and light.

    abstract::Exposure of 4-methoxy-2-(3-phenyl-2-propynyl)phenol (CO/1828) to air and light (accelerated by temperature) yields 1-(2-hydroxy-5- methoxyphenyl)-3-phenylpropynone as the major degradation product. With extraction, this product rapidly degrades to 5-methoxyaurone and 6-methoxyflavone. In addition, a mixture of dimeric...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810818

    authors: Schiavi M,Serafini S,Italia A,Villa M,Fronza G,Selva A

    更新日期:1992-08-01 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

  • Effect of characteristics of compounds on maintenance of an amorphous state in solid dispersion with crospovidone.

    abstract::Solid dispersion (SD) of indomethacin with crospovidone (CrosPVP) shows useful characteristics for preparation of dosage forms. This study aimed to determine the types of drugs that could adopt a stable amorphous form in SD. Twenty compounds with various melting points (70-218 degrees C), molecular weights (135-504) a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20794

    authors: Shibata Y,Fujii M,Kokudai M,Noda S,Okada H,Kondoh M,Watanabe Y

    更新日期:2007-06-01 00:00:00

  • Extraction and analysis by high-performance liquid chromatography of antibiotics in a drug delivery system for farmed fish.

    abstract::Simple assays for extraction and determination of the concentrations of the antibiotics oxytetracycline, oxolinic acid, and flumequine in a drug dosage form for farmed fish are described. HPLC with UV detection was used in the analyses. The recovery of all three drugs was approximately 100%, and the precision varied f...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600820517

    authors: Rogstad A,Weng B

    更新日期:1993-05-01 00:00:00

  • Progesterone retention by rat uterus I. Pharmacokinetics after uterine intraluminal instillation.

    abstract::Tritium-labeled progesterone was administered to mature female rats in the proestrous stage by three different routes, gastric intubation, subcutaneous injection, and uterine intraluminal instillation, to study the kinetics involved in the uptake and retention of radioactivity by the uterus and various other tissues. ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600661223

    authors: Fang SM,Lin CS,Lyon V

    更新日期:1977-12-01 00:00:00

  • A mechanistic and kinetic study of the beta-lactone hydrolysis of Salinosporamide A (NPI-0052), a novel proteasome inhibitor.

    abstract::The aim of the present study was to investigate the mechanism of aqueous degradation of Salinosporamide A (NPI-0052; 1), a potent proteasome inhibitor that is currently in Phase I clinical trials for the treatment of cancer and is characterized by a unique beta-lactone-gamma-lactam bicyclic ring structure. The degrada...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20835

    authors: Denora N,Potts BC,Stella VJ

    更新日期:2007-08-01 00:00:00

  • Enhancing Intestinal Absorption of a Model Macromolecule via the Paracellular Pathway using E-Cadherin Peptides.

    abstract::Membrane permeation enhancers have received significant attention in recent years for enabling the oral absorption of poorly permeable drug molecules. In this study, we investigated the ability of His-Ala-Val (HAV) and Ala-Asp-Thr (ADT) peptides derived from the extracellular-1 (EC1) domain of E-cadherin proteins to i...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.12.018

    authors: Dening TJ,Siahaan TJ,Hageman MJ

    更新日期:2020-12-23 00:00:00

  • The use of xanthan gum in an ophthalmic liquid dosage form: rheological characterization of the interaction with mucin.

    abstract::The development of an ocular dosage form containing xanthan gum and capable of interacting with mucin in the precorneal area is a challenge. The polymer concentration that can be applied is restricted because of the limited patient acceptability of highly viscous preparations. The precorneal mucin concentration is low...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10106

    authors: Ceulemans J,Vinckier I,Ludwig A

    更新日期:2002-04-01 00:00:00

  • Combined assay, identification, and foreign related steroids test for methandrostenolone by high-speed liquid chromatography.

    abstract::A high-speed liquid chromatographic system is described, which can be used for the simultaneous identification of the anabolic steroid methandrostenolone and its impurities and the quantitation of each of these compounds. Separation is effected by adsorption chromatography on a slurry-packed microparticulate silica ge...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600640319

    authors: Butterfield AG,Lodge BA,Pound NJ,Sears RW

    更新日期:1975-03-01 00:00:00

  • Dissolution rate studies of compression-molded units made from hydroxypropyl cellulose films.

    abstract::Hydroxypropyl cellulose films were prepared by compression molding of three different lots of hydroxypropyl cellulose powder at 149 degrees C, 188 degrees C, and 232 degrees C. Rectangular pieces were cut from these films and viscosity average molecular weight (Mv), degree of orientation, and rate of dissolution were ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600740509

    authors: Grabowski LA,Bondi JV,Harwood RJ

    更新日期:1985-05-01 00:00:00

  • Forced degradation studies of corticosteroids with an alumina-steroid-ethanol model for predicting chemical stability and degradation products of pressurized metered-dose inhaler formulations.

    abstract::An alumina (Al(2)O(3))-steroid-ethanol model is used for forced degradation testing of corticosteroids to predict chemical stability and degradation products in pressurized metered-dose inhaler (pMDI) solution formulations. The model involves an ethanolic solution of a test steroid with Al(2)O(3), stressed at elevated...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23111

    authors: Wu ZZ,Thatcher ML,Lundberg JK,Ogawa MK,Jacoby CB,Battiste JL,Ledoux KA

    更新日期:2012-06-01 00:00:00

  • Injectable polyanhydride granules provide controlled release of water-soluble drugs with a reduced initial burst.

    abstract::A method for preparing polyanhydride granules of an injectable size was developed. The resulting granules permitted a nearly constant release of low-molecular-weight, water-soluble drugs without an initial burst. The polyanhydrides used were poly(fatty acid dimer), poly(sebacic acid), and their copolymers. The dyes ac...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600830104

    authors: Tabata Y,Domb A,Langer R

    更新日期:1994-01-01 00:00:00

  • Interactions of pluronic block copolymers on P-gp efflux activity: experience with HIV-1 protease inhibitors.

    abstract::The objective was to examine the influence of Pluronic block-copolymers on the interaction between the drug efflux transporter, P-glycoprotein and HIV-1 protease inhibitors (PIs). The ATPase assay determined the effect of various Pluronics on PI-stimulated P-gp ATPase activity. Cellular accumulation studies were condu...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21372

    authors: Shaik N,Pan G,Elmquist WF

    更新日期:2008-12-01 00:00:00

  • Dissolution rates of corticoid solutions dispersed on silicas.

    abstract::Two nonporous and three porous amorphous silicas were used as dispersion media to convert corticoid solutions into free-flowing powders. The corticoids (prednisone, prednisolone, and hydrocortisone) were dissolved in N,N-dimethylacetamide-polyethylene glycol 400 (7:3 v/v) and their 10% (w/v) solutions were mixed with ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600730330

    authors: Liao CC,Jarowski CI

    更新日期:1984-03-01 00:00:00