Enhancing the Pharmaceutical Behavior of Nateglinide by Cocrystallization: Physicochemical Assessment of Cocrystal Formation and Informed Use of Differential Scanning Calorimetry for Its Quantitative Characterization.

Abstract:

:The aim of this study was to synthetize cocrystals of nateglinide, an antidiabetic agent of biopharmaceutics classification system Class IIa, as a strategy to improve both the solubility and the dissolution rate of the drug. Benzamide was selected by a screening procedure as a suitable coformer, and binary mixtures with different compositions were prepared and analyzed by differential scanning calorimetry (DSC). An in-depth analysis of DSC data allowed obtaining both the eutectic mixture and cocrystal compositions. The rationale of such an analysis was highlighted and explained. Cocrystals were prepared by kneading and solvent evaporation. Their formation was proved by DSC and confirmed by X-ray powder diffraction, solid-state nuclear magnetic resonance, and Fourier-transform infrared spectroscopy. The functional groups involved in the interaction leading to cocrystals formation were investigated by spectroscopic techniques. The in vitro dissolution profiles show that cocrystals have definite better pharmaceutical performances than the pure drug.

journal_name

J Pharm Sci

authors

Bruni G,Maggi L,Mustarelli P,Sakaj M,Friuli V,Ferrara C,Berbenni V,Girella A,Milanese C,Marini A

doi

10.1016/j.xphs.2018.11.033

subject

Has Abstract

pub_date

2019-04-01 00:00:00

pages

1529-1539

issue

4

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(18)30781-0

journal_volume

108

pub_type

杂志文章
  • Influence of excipients, drugs, and osmotic agent in the inner core on the time-controlled disintegration of compression-coated ethylcellulose tablets.

    abstract::The effect of excipient, drug, and osmotic agent loaded in the inner core tablet on the time-controlled disintegration of compression-coated tablet prepared by direct compression with micronized ethylcellulose was investigated. The excipients [spray-dried lactose, hydroxypropyl methyl cellulose, sodium starch glycolat...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10197

    authors: Lin SY,Lin KH,Li MJ

    更新日期:2002-09-01 00:00:00

  • Mechanism of phosphate adsorption to a three-dimensional structure of boehmite in the presence of bovine serum albumin.

    abstract::A new microcrystalline boehmite (tentatively named PT-A) was synthesized as an efficient phosphate adsorbent to replace aluminum hydroxide gel. The characteristic structure of PT-A was examined by nitrogen adsorption/desorption, X-ray diffraction, deviation microscopy, and scanning electron microscopy to establish a p...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600820714

    authors: Ookubo A,Nishida M,Ooi K,Ishida K,Hashimura Y,Ikawa A,Yoshimura Y,Kawada J

    更新日期:1993-07-01 00:00:00

  • Simultaneous GLC determination of methyl salicylate and menthol in a topical analgesic formulation.

    abstract::A simultaneous GLC determination for methyl salicylate and menthol in a topical analgesic formulation is reported. n-Nonadecane is used as the internal standard. The method is rapid, accurate, precise, and selective in the presence of salicylic acid and ethyl salicylate. ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680431

    authors: Sapio JP,Sethachutkul K,Moody JE

    更新日期:1979-04-01 00:00:00

  • Effect of Controlled Ice Nucleation on Stability of Lactate Dehydrogenase During Freeze-Drying.

    abstract::Several controlled ice nucleation techniques have been developed to increase the efficiency of the freeze-drying process as well as to improve the quality of pharmaceutical products. Owing to the reduction in ice surface area, these techniques have the potential to reduce the degradation of proteins labile during free...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2017.10.020

    authors: Fang R,Tanaka K,Mudhivarthi V,Bogner RH,Pikal MJ

    更新日期:2018-03-01 00:00:00

  • Stability of tetrahydrocannabinols II.

    abstract::The biphasic degradation of delta9-tetrahydrocannabinol (I), as monitored by flame-ionization GLC, produced delta8-tetrahydrocannabinol (II), cannabidiol (X), 9-hydroxyhexahydrocannabinol (VI), 9,10-dihydro-9-hydroxyisocannabidiol (VI), and and 6,12-dihydro-6-hydroxycannabidiol (VIII) in acidic solutions. Further iden...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670108

    authors: Garrett ER,Gouyette AJ,Roseboom H

    更新日期:1978-01-01 00:00:00

  • Mass spectrometry of chlorambucil, its degradation products, and its metabolite in biological samples.

    abstract::A sensitive and specific method for the determination of chlorambucil and its metabolite in biological fluids is reported. The method is based on selected-ion monitoring detection following simple extraction of the parent compound, its metabolite, and an internal standard (chlorambucil-d8) from plasma and urine sample...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600690122

    authors: Chang SY,Larcom BJ,Alberts DS,Larsen B,Walson PD,Sipes IG

    更新日期:1980-01-01 00:00:00

  • Complexation of steroid hormones with cyclodextrin derivatives: substituent effects of the guest molecule on solubility and stability in aqueous solution.

    abstract::The inclusion complexation of homologous derivatives of steroid hormones with cyclodextrins and 2-hydroxypropyl-beta-cyclodextrin (2-HP-beta-CD) was investigated with regard to underlying structure-interaction relationship. The interaction was studied by phase solubility analysis and stabilization effects of complex f...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810808

    authors: Albers E,Müller BW

    更新日期:1992-08-01 00:00:00

  • Monitoring the film coating unit operation and predicting drug dissolution using terahertz pulsed imaging.

    abstract::Understanding the coating unit operation is imperative to improve product quality and reduce output risks for coated solid dosage forms. Three batches of sustained-release tablets coated with the same process parameters (pan speed, spray rate, etc.) were subjected to terahertz pulsed imaging (TPI) analysis followed by...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21766

    authors: Ho L,Müller R,Gordon KC,Kleinebudde P,Pepper M,Rades T,Shen Y,Taday PF,Zeitler JA

    更新日期:2009-12-01 00:00:00

  • Thyroxine revisited.

    abstract::The crystal structure of the common therapeutic agent, the pentahydrated sodium salt of L-thyroxine hormone (3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine), has been determined and discussed in relation to the drug's stability. The stoichiometry and absolute configuration (-)-C(8)S-[C15H10I4NO4]-.Na+....

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20155

    authors: Katrusiak A,Katrusiak A

    更新日期:2004-12-01 00:00:00

  • Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state.

    abstract::Though there is an advantage in using the higher solubility amorphous state in cases where low solubility limits absorption, physical instability poses a significant barrier limiting its use in solid oral dosage forms. Unlike chemical instability, where useful accelerated stability testing protocols are common, no met...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1002/jps.21138

    authors: Bhugra C,Pikal MJ

    更新日期:2008-04-01 00:00:00

  • Characterization of the physical stability of a lyophilized IgG1 mAb after accelerated shipping-like stress.

    abstract::Upon exposure to shaking stress, an IgG1 mAb formulation in both the liquid and lyophilized state formed subvisible particles. Because freeze-drying was expected to minimize protein physical instability under these conditions, the extent and nature of aggregate formation in the lyophilized preparation were examined us...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24242

    authors: Telikepalli S,Kumru OS,Kim JH,Joshi SB,O'Berry KB,Blake-Haskins AW,Perkins MD,Middaugh CR,Volkin DB

    更新日期:2015-02-01 00:00:00

  • Solubility and partitioning. VII: Solubility of barbiturates in water.

    abstract::The solubility equation of Yalkowsky was used to estimate the aqueous solubility of 33 barbiturates in the temperature range of 5 to 45 degrees C. The equation was extended by adding a term which accounts for the effect of pH on the solubility of the drug. The extended equation is successful in estimating the aqueous ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600760120

    authors: Pinal R,Yalkowsky SH

    更新日期:1987-01-01 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

  • Pharmacokinetic study of methotrexate following intra-articular injection of methotrexate loaded poly(L-lactic acid) microspheres in rabbits.

    abstract::The pharmacokinetics and tissue distribution of methotrexate (MTX) were investigated following intra-articular injection of either MTX solution or controlled release MTX loaded microspheres in healthy rabbit joints. MTX solution or MTX loaded microspheres (size 30-100 mum) (10 mg MTX) was injected into the right knee ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20341

    authors: Liang LS,Wong W,Burt HM

    更新日期:2005-06-01 00:00:00

  • Influence of non-water-soluble placebo pellets of different sizes on the characteristics of orally disintegrating tablets manufactured by freeze-drying.

    abstract::The present study describes the development of an orally disintegrating tablet containing a non-water-soluble drug delivery system. A model system was applied to evaluate the effect of different-sized particles on tablet characteristics. Cellets were incorporated into tablets prepared by freeze-drying from a 100 mg/mL...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23517

    authors: Stange U,Führling C,Gieseler H

    更新日期:2013-06-01 00:00:00

  • Definition of a solvent system for spherical crystallization of salbutamol sulfate by quasi-emulsion solvent diffusion (QESD) method.

    abstract::In this paper we describe how the spherical crystallization process by QESD method can be applied to a water-soluble drug, salbutamol sulfate. The type of solvent, antisolvent, and emulsifier and the concentration of emulsifier to be used for the production of spherical particles with a size range 80-500 microm are de...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.1112

    authors: Nocent M,Bertocchi L,Espitalier F,Baron M,Couarraze G

    更新日期:2001-10-01 00:00:00

  • Potential thyroliberin affinity labels II: Chloroacetyl substituted phenylalanyl prolineamides.

    abstract::Three analogs of thyroliberin (I) were prepared. These compounds, N-m-chloroacetylbenzoyl-phenylalanyl-prolineamide (VIa), N-p-chloroacetylbenzoyl-phenylalanyl-prolineamide (VIb) and N-chloroacetyl-alanyl-phenylalanyl-prolineamide (IX), were designed as potential I antagonist affinity labels. However, no significant a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600710928

    authors: Goebel RJ,Currie BL,Bowers CY

    更新日期:1982-09-01 00:00:00

  • Use of supercritical fluid extraction for sample preparation of sustained-release felodipine tablets.

    abstract::Supercritical fluid extraction (SFE) was shown to be an accurate and precise alternative to liquid extraction for sample preparation of sustained-release felodipine tablets (5 mg potency) while realizing an 80% reduction in solvent consumption. Extractions of felodipine spiked on an inert support were used to evaluate...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600831104

    authors: Howard AL,Shah MC,Ip DP,Brooks MA,Strode JT 3rd,Taylor LT

    更新日期:1994-11-01 00:00:00

  • 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

  • Reversed-phase ion-pair chromatography of tetracycline, tetracycline analogs, and their potential impurities.

    abstract::Methods are presented for the separation of tetracycline, tetracycline analogs, and their potential impurities by reversed-phase ion-pair chromatography. The mobile phase consisted of a phosphate buffer with tripropylamine or N,N-dimethyloctylamine as counterions and acetonitrile as the organic modifier. The chromatog...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600710221

    authors: Hermansson J,Andersson M

    更新日期:1982-02-01 00:00:00

  • Preparation and evaluation of Eudragit gels. III: Rectal gel preparations for sustained release of pentoxifylline.

    abstract::A novel method was established for the preparation of Eudragit S, Eudragit L, and Eudispert high-viscosity (hv) hydrogel and xerogel preparations containing a medicinal component such as pentoxifylline (an agent that improves cerebral microcirculation). A significant correlation was found between the in vitro mean dis...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810613

    authors: Kim NS,Kawata M,Uchida T,Goto S

    更新日期:1992-06-01 00:00:00

  • Miscibility studies of indomethacin and Eudragit® E PO by thermal, rheological, and spectroscopic analysis.

    abstract::The objective of this study is to understand the underlying mechanisms responsible for the superior stability of indomethacin (INM)-Eudragit® E PO (E PO) system by exploring the miscibility and intermolecular interactions through the combination of thermal, rheological, and spectroscopic analysis. The zero shear-rate ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23075

    authors: Liu H,Zhang X,Suwardie H,Wang P,Gogos CG

    更新日期:2012-06-01 00:00:00

  • Skin penetration of nonsteroidal antiinflammatory drugs out of a lipophilic vehicle: influence of the viable epidermis.

    abstract::The skin penetration of 10 nonsteroidal antiinflammatory drugs (NSAIDs) was investigated after application in the lipophilic vehicle light mineral oil. The skin permeabilities and maximum fluxes, which were calculated from the concentration decreases of the applied solutions in the steady state phases, were correlated...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 临床试验,杂志文章

    doi:10.1021/js990032o

    authors: Wenkers BP,Lippold BC

    更新日期:1999-12-01 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

  • Diffusion and concentration profiles of drugs in gels.

    abstract::A versatile membraneless method was used to study the diffusion of acetaminophen, ibuprofen, indomethacin, theophylline, and chlorpheniramine in thermoreversible gels. Two independent ways to calculate the diffusion coefficients and to verify Fickian transport are presented; the most sensitive criterion for Fickian tr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600821106

    authors: Upadrashta SM,Häglund BO,Sundelöf LO

    更新日期:1993-11-01 00:00:00

  • High-pressure liquid chromatographic determination of cimetidine in plasma and urine.

    abstract::An assay is described for the determination of the H2-receptor antagonist, cimetidine, in human plasma and urine. Alkalinized plasma or urine was extracted with methylene chloride, the organic phase was evaporated, and the reconstituted residue was analysed by high-pressure liquid chromatography (HPLC) using a reverse...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600710528

    authors: Mihaly GW,Cockbain S,Jones DB,Hanson RG,Smallwood RA

    更新日期:1982-05-01 00:00:00

  • Synthesis and evaluation of N-nicotinoyl-2-{2-(2-methyl-5-nitroimidazol-1-yl)ethyloxy}-D,L-glycine as a colon-specific prodrug of metronidazole.

    abstract::Metronidazole (MTZ) is a drug of choice for protozoal infections such as luminal amoebiasis. We designed and synthesized N-nicotinoyl-2-{2-(2-methyl-5-nitroimidazol-1-yl)ethyloxy}-D,L-glycine (NMG) as a colon-specific prodrug of MTZ. The synthetic yield of NMG was about 34%. The apparent partition coefficient of MTZ w...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21720

    authors: Kim D,Hong S,Jung S,Jung Y,Kim YM

    更新日期:2009-11-01 00:00:00

  • Pharmaceutical impurity identification: a case study using a multidisciplinary approach.

    abstract::A multidisciplinary team approach to identify pharmaceutical impurities is presented in this article. It includes a representative example of the methodology. The first step is to analyze the sample by LC-MS. If the structure of the unknown impurity cannot be conclusively determined by LC-MS, LC-NMR is employed. If th...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20120

    authors: Alsante KM,Boutros P,Couturier MA,Friedmann RC,Harwood JW,Horan GJ,Jensen AJ,Liu Q,Lohr LL,Morris R,Raggon JW,Reid GL,Santafianos DP,Sharp TR,Tucker JL,Wilcox GE

    更新日期:2004-09-01 00:00:00

  • Pharmacokinetics and disposition of a localized lymphatic polymeric hyaluronan conjugate of cisplatin in rodents.

    abstract::Cisplatin (CDDP) is an effective anticancer agent for many solid tumors but has significant systemic toxicity limiting its use in many patients. We have designed a loco-regional delivery system to increase platinum levels in the lymphatics, where early metastasis is most likely to occur, while reducing systemic toxici...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22016

    authors: Cai S,Xie Y,Davies NM,Cohen MS,Forrest ML

    更新日期:2010-06-01 00:00:00

  • pH-Sensitive cationic copolymers of different macromolecular architecture as potential dexamethasone sodium phosphate delivery systems.

    abstract::This paper describes the synthesis and characterization of cationic copolymers with different macromolecular architecture and drug delivery properties of the corresponding dexamethasone sodium phosphate (DSP)-loaded systems. Copolyelectrolytes comprising poly[2-(acryloyloxy)ethyl] trimethylammonium chloride (PAETMAC) ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24059

    authors: Georgieva D,Kostova B,Ivanova S,Rachev D,Tzankova V,Kondeva-Burdina M,Christova D

    更新日期:2014-08-01 00:00:00