Role of Solvent Selection on Crystal Habit of 5-Aminosalicylic Acid-Combined Experimental and Computational Approach.

Abstract:

:Many active pharmaceutical ingredients exhibit a needle-like (acicular) crystal habit, which can significantly complicate their downstream processing. In this study, the acicular crystal habit of a model active pharmaceutical ingredient, 5-aminosalicylic acid (5-ASA), was modified by addition of selected organic solvents to the typical aqueous crystallization process. 5-ASA was crystallized by a pH shift from 7.5-8 to 4 in the presence of methanol, acetonitrile, acetone, tetramethylurea, tetrahydrofuran or dimethyl sulfoxide at 25% v/v, or butanol at 9% v/v. Changes to the experimentally observed crystal habit are rationalized by considering adsorption energy calculations for the solvent molecules onto the morphologically important crystal faces. The crystal habit was influenced most significantly by organic solvents containing a good H-bond acceptor atom, particularly oxygen in acetone, tetramethylurea, tetrahydrofuran, and dimethyl sulfoxide. Such solvents have strongly stabilizing adsorption energies onto the fast-growing crystal faces, and their presence in solution thereby serves to modify the acicular habit of 5-ASA. The developed knowledge base on crystal interface-solvent interactions can form a basis for further engineering of an optimal crystal habit for 5-ASA.

journal_name

J Pharm Sci

authors

Pudasaini N,Parker CR,Hagen SU,Bond AD,Rantanen J

doi

10.1016/j.xphs.2017.12.005

subject

Has Abstract

pub_date

2018-04-01 00:00:00

pages

1112-1121

issue

4

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(17)30875-4

journal_volume

107

pub_type

杂志文章
  • Three-Dimensional Printing of Carbamazepine Sustained-Release Scaffold.

    abstract::Carbamazepine is the first-line anti-epileptic drug for focal seizures and generalized tonic-clonic seizures. Although sustained-release formulations exist, an initial burst of drug release is still present and this results in side effects. Zero-order release formulations reduce fluctuations in serum drug concentratio...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2016.04.031

    authors: Lim SH,Chia SM,Kang L,Yap KY

    更新日期:2016-07-01 00:00:00

  • Molecular connectivity analyses of structure influencing chromatographic retention indexes.

    abstract::The molecular connectivity indexes of various aliphatic alcohols, ketones, ethers, and esters were used to describe structural features influencing chromatographic retention indexes. Good correlations were obtained within chemical classes for a particular stationary phase. ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680143

    authors: Kier LB,Hall LH

    更新日期:1979-01-01 00:00:00

  • Kinetic ratio as a parameter for product stability calculations.

    abstract::A new parameter, the kinetic ratio, is suggested for estimating product potency during storage under ambient warehouse temperatures. Actual warehouse temperature data were integrated using Arrhenius kinetics, and the resulting potency errors, due both to the integration method and to temperature averaging, were evalua...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600690318

    authors: Scher M

    更新日期:1980-03-01 00:00:00

  • Differentiation of subvisible silicone oil droplets from irregular standard dust particles.

    abstract::New methods are being applied to distinguish silicone oil droplets from subvisible particles in therapeutic protein formulations. The need to standardize these methods and compare them to established methods is critical to increase the understanding of the risks from protein aggregation and other subvisible particulat...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23554

    authors: Vandesteeg N,Kilbert C

    更新日期:2013-06-01 00:00:00

  • Enhancing effects of lipophilic vehicles on skin penetration of methyl nicotinate in vivo.

    abstract::Vehicle effects may be caused by thermodynamic effects and by specific (penetration enhancing) effects. To investigate the effects of various lipophilic vehicles on drug penetration, an in vivo permeability study was conducted with methyl nicotinate as the model drug. The drug was dissolved in the respective vehicles ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 临床试验,杂志文章

    doi:10.1002/jps.2600840214

    authors: Leopold CS,Lippold BC

    更新日期:1995-02-01 00:00:00

  • Metabolism and measurement of chloroprocaine, an ester-type local anesthetic.

    abstract::Blood levels of intact chloroprocaine were determined using a GLC procedure capable of detecting as little as 10 ng of chloroprocaine/ml of blood. It was necessary to detective plasma cholinesterases in collected samples by adding echothiophate iodide to blood sampling tubes. An extraction procedure, followed by a TLC...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680123

    authors: O'Brien JE,Abbey V,Hinsvark O,Perel J,Finster M

    更新日期:1979-01-01 00:00:00

  • Pharmacokinetics of methylphenidate in the rat using single-ion monitoring GLC-mass spectrometry.

    abstract::A GLC-mass spectrometric assay for methylphenidate in biological fluids was developed using the ethyl ester homolog of the drug as the internal standard. The procedure has a lower level of sensitivity of 1.2 ng/ml and is based on GLC-mass spectrometic monitoring of the m/e 180 ion common to the mass spectra of the N-t...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600660633

    authors: Gal J,Hodshon BJ,Pintauro C,Flamm BL,Cho AK

    更新日期:1977-06-01 00:00:00

  • Determination of time course of tablet disintegration II: Method using continuous functions.

    abstract::An analysis of the disintegration-dissolution sequence of drug release from a tablet leads to a mathematical expression relating disintegration to the dissolution profile of the tablet and the dissolution rate of the primary drug particles in the tablet. The equation describing the disintegration of an acetaminophen t...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670122

    authors: Nelson KG,Wang LY

    更新日期:1978-01-01 00:00:00

  • Establishment of a Drug-Induced, Bile Acid-Dependent Hepatotoxicity Model Using HepaRG Cells.

    abstract::Bile acid (BA) retention within hepatocytes is an underlying mechanism of cholestatic drug-induced liver injury (DILI). We previously developed an assay using sandwich-cultured human hepatocytes (SCHHs) to evaluate drug-induced hepatocyte toxicity accompanying intracellular BA accumulation. However, due to shortcoming...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2016.01.013

    authors: Susukida T,Sekine S,Nozaki M,Tokizono M,Oizumi K,Horie T,Ito K

    更新日期:2016-04-01 00:00:00

  • Differential elimination of synthetic butyric triglycerides in vivo: a pharmacokinetic study.

    abstract::New butyrate derivatives were synthesized to investigate the residence time of potent butyric acid in vivo. These derivatives were triglycerides in which one, two, or three butyric acid molecules were bound to glycerol or to mono- and dipalmitic esters of glycerol. Pharmacokinetic studies showed that a constant plasma...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:

    authors: Planchon P,Pouillart P,Ronco G,Villa P,Pieri F

    更新日期:1993-10-01 00:00:00

  • Physiologically Based Pharmacokinetic Modeling to Supplement Nilotinib Pharmacokinetics and Confirm Dose Selection in Pediatric Patients.

    abstract::In adult patients, nilotinib is indicated for chronic myeloid leukemia at an approved oral dose of 300 or 400 mg BID. Physiologically based pharmacokinetic (PBPK) model was developed to describe and supplement limited PK data in the pediatric population ranging from 2 to less than 6 years of age and ultimately inform ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2019.01.028

    authors: Heimbach T,Lin W,Hourcade-Potelleret F,Tian X,Combes FP,Horvath N,He H

    更新日期:2019-06-01 00:00:00

  • Polyanhydride microsphere formulation by solvent extraction.

    abstract::A novel process based on solvent extraction was developed to produce drug-loaded polyanhydride microspheres for controlled-release applications. The technique consists of adding a chloroform solution of polyanhydride and drug into a stirred silicone oil phase containing suspended droplets of surfactant. No chemical re...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600770811

    authors: Bindschaedler C,Leong K,Mathiowitz E,Langer R

    更新日期:1988-08-01 00:00:00

  • Incidence of experimental fascioliasis on hepatic disposition of [3H]tetracycline and [14C]rafoxanide in rats.

    abstract::[7-3H]Tetracycline and [carbonyl-14C]rafoxanide were injected intravenously into anesthetized controls and rats in which experimental fascioliasis had been induced by 20 Fasciola hepatica metacercariae. The biliary excretion (1 and 3 h, respectively) of the radioactivity consisted of approximately 4% of the administer...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600740921

    authors: Galtier P,Larrieu G,Franc M

    更新日期:1985-09-01 00:00:00

  • Probing the Tryptophan Environment in Therapeutic Proteins: Implications for Higher Order Structure on Tryptophan Oxidation.

    abstract::Tryptophan (Trp) oxidation in proteins leads to a number of events, including changes in color, higher order structure (HOS), and biological activity. We describe here a number of new findings through a comprehensive characterization of 6 monoclonal antibodies (mAbs) following selective oxidation of Trp residues by 2,...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2018.12.027

    authors: Barnett GV,Balakrishnan G,Chennamsetty N,Hoffman L,Bongers J,Tao L,Huang Y,Slaney T,Das TK,Leone A,Kar SR

    更新日期:2019-06-01 00:00:00

  • Determination of a cephalosporin antibiotic, ceftibuten, in human plasma with column-switching high-performance liquid chromatography with ultraviolet detection.

    abstract::A column-switching high-performance liquid chromatographic assay combined with a heart-cutting technique and UV detection (LC/LC/UV) was developed to determine ceftibuten, a new oral cephalosporin, in human plasma. Plasma samples were directly injected into the first chromatographic column for sample cleanup and extra...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810715

    authors: Pan HT,Kumari P,Lim J,Lin CC

    更新日期:1992-07-01 00:00:00

  • Preparation and Characterization of Ascosome Vesicles Loaded with Khellin.

    abstract::Ascorbic acid has a unique role in the prevention and treatment of a large number of chronic diseases, including skin disorders but it can hardly penetrate the skin due to its solubility in water and its high instability. This study explored the formation of phosphatidylcholine-based vesicles upon addition of ascorbyl...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.06.017

    authors: Risaliti L,Ambrosi M,Calamante M,Bergonzi MC,Lo Nostro P,Bilia AR

    更新日期:2020-10-01 00:00:00

  • Dequaternization of curare bases with sodium thiophenoxide and ethanolamine.

    abstract::To prepare (+)-tubocurine and O,O-dimethyl-(+)-tubocurine, the commonly used dequaternization procedures with sodium theophenoxide and ethanolamine were investigated. The quaternary compounds were (+)-tubocurarine chloride and the chloride and iodide salts of O,O-dimethyl-(+)-chondocurarine. The results obtained with ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670904

    authors: Naghaway JA,Soine TO

    更新日期:1978-09-01 00:00:00

  • Effect of food on the bioavailability of lisinopril, a nonsulfhydryl angiotensin-converting enzyme inhibitor.

    abstract::A randomized, two-way, crossover study was performed on 18 normal volunteers to assess the influence of food on the bioavailability of lisinopril, (1-[N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl]-L-proline), a long-acting nonsulfhydryl angiotensin converting enzyme inhibitor. A single, 20-mg oral dose of lisinopril was ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 临床试验,杂志文章,随机对照试验

    doi:10.1002/jps.2600750416

    authors: Mojaverian P,Rocci ML Jr,Vlasses PH,Hoholick C,Clementi RA,Ferguson RK

    更新日期:1986-04-01 00:00:00

  • Comparative study of interaction mode of diazepines with human serum albumin and alpha 1-acid glycoprotein.

    abstract::The binding of nine diazepines to human serum albumin (HSA) and to alpha 1-acid glycoprotein (AGP) was investigated by means of fluorescence and circular dichroism (CD) spectroscopies. The binding parameters of diazepam obtained from fluorescence agreed with those obtained from CD measurements. Diazepines have one tig...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810104

    authors: Maruyama T,Furuie MA,Hibino S,Otagiri M

    更新日期:1992-01-01 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

  • Effect of tumor necrosis factor-alpha and interferon-gamma on intestinal P-glycoprotein expression, activity, and localization in Caco-2 cells.

    abstract::The P-glycoprotein (Pgp), a drug efflux pump, is expressed in intestinal epithelial cells, where it constitutes a barrier against xenobiotics. In inflammatory bowel disease, a dysregulation in the production of tumor necrosis factor (TNF)alpha and interferon (IFN)gamma, and an alteration of Pgp expression and activity...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20072

    authors: Belliard AM,Lacour B,Farinotti R,Leroy C

    更新日期:2004-06-01 00:00:00

  • Passive Immunotherapies Targeting Amyloid Beta and Tau Oligomers in Alzheimer's Disease.

    abstract::Alzheimer's disease (AD) is historically difficult to treat, in part because of the inaccessible nature of brain pathology. Amyloid beta and tau proteins drive pathology by forming toxic oligomers that eventually deposit as insoluble amyloid plaques and neurofibrillary tangles. Recent clinical studies suggest that eff...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2019.10.024

    authors: Vander Zanden CM,Chi EY

    更新日期:2020-01-01 00:00:00

  • Calorimetric and spectroscopic studies on the interaction of methimazole with bovine serum albumin.

    abstract::The potential binding interaction(s) of the anti-thyroid drug methimazole (MMZ) with the protein bovine serum albumin (BSA) has been studied using isothermal titration calorimetry (ITC) and UV-Visible, fluorescence and circular dichroism (CD) spectroscopic techniques. The binding of MMZ to BSA has been studied in both...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21140

    authors: Singh SK,Kishore N

    更新日期:2008-06-01 00:00:00

  • Dynamics of disinfection of selected preservatives against Escherichia coli.

    abstract::Mathematical models were determined relating preservative concentration and D values (decimal reduction times at 25 degrees C; pH 6.9-7.1) against Escherichia coli in aqueous medium. Preservatives investigated were 2-bromo-2-nitro-1,3-propanediol (Bronopol), N-(hydroxymethyl)-N-(1,3-dihydroxymethyl-2, 5-dioxo-4-imidaz...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600740820

    authors: Hurwitz SJ,McCarthy TJ

    更新日期:1985-08-01 00:00:00

  • Dietary polyphenols (-)-epicatechin and chrysin inhibit intestinal glucuronidation metabolism to increase drug absorption.

    abstract::The effect of dietary polyphenols on the intestinal glucuronidation and absorption of a model phenolic drug, alpha-naphthol (alpha-NA), was studied in isolated rat small intestine. (-)-Epicatechin significantly inhibited the glucuronidation of alpha-NA. Chrysin, (-)-epigallocatechin galleate (EGCG), and quercetin decr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20146

    authors: Mizuma T,Awazu S

    更新日期:2004-09-01 00:00:00

  • Association efficiency of three ionic forms of oxytetracycline to cationic and anionic oil-in-water nanoemulsions analyzed by diafiltration.

    abstract::The association efficiency of oxytetracycline (OTC) to pharmaceutical available, ionic oil-in-water nanoemulsions is studied. Theoretical mathematical developments allowed us to differentiate by diafiltration (DF) between thermodynamically and kinetically controlled binding of the drug to the nanoemulsions, and relate...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24255

    authors: Orellana SL,Torres-Gallegos C,Araya-Hermosilla R,Oyarzun-Ampuero F,Moreno-Villoslada I

    更新日期:2015-03-01 00:00:00

  • Nondestructive measurements of the compact strength and the particle-size distribution after milling of roller compacted powders by near-infrared spectroscopy.

    abstract::Compact strength and the particle-size distribution of milled roller compacted compacts were correlated to the slope of the best-fit line through near-infrared spectra for samples prepared under different roll speeds and feed rates. The above correlations were found to hold for compacts prepared from microcrystalline ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20003

    authors: Gupta A,Peck GE,Miller RW,Morris KR

    更新日期:2004-04-01 00:00:00

  • Determination of safrole, dihydrosafrole, and chloromethyldihydrosafrole in piperonyl butoxide by high-performance liquid chromatography.

    abstract::An HPLC method for the simultaneous determination of safrole (S), dihydrosafrole (DHS), and chloromethyldihydrosafrole (CM-DHS) in piperonyl butoxide, with fluorimetric detection and elution gradient, is described. Samples with internal standard (piperonyl isobutyrate) are adsorbed on silica cartridges, then eluted wi...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600820812

    authors: Schreiber-Deturmeny EM,Pauli AM,Pastor JL

    更新日期:1993-08-01 00:00:00

  • Lyotropic liquid crystals and the structural lipids of the stratum corneum.

    abstract::Lipids were extracted from human stratum corneum and the remaining corneocytes were reaggregated with different lyotropic liquid crystals. Water transport through the reaggregated stratum corneum was determined using a diffusion chamber according to Smith and Blank. The permeability constant for the reaggregated strat...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600800506

    authors: Kayali I,Suhery T,Friberg SE,Simion FA,Rhein LD

    更新日期:1991-05-01 00:00:00

  • Protein adsorption, desorption, and aggregation mediated by solid-liquid interfaces.

    abstract::Adsorption of proteins to solid-fluid interfaces is often empirically found to promote formation of soluble aggregates and larger, subvisible, and visible particles, but key stages in this process are often difficult to probe directly. Aggregation mediated by adsorption to water-silicon oxide (SiOx) interfaces, akin t...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24429

    authors: Perevozchikova T,Nanda H,Nesta DP,Roberts CJ

    更新日期:2015-06-01 00:00:00