Solid-Phase and Oscillating Solution Crystallization Behavior of (+)- and (-)-N-Methylephedrine.

Abstract:

:This work involves the study of the solid-phase and solution crystallization behavior of the N-methylephedrine enantiomers. A systematic investigation of the melt phase diagram of the enantiomeric N-methylephedrine system was performed considering polymorphism. Two monotropically related modifications of the enantiomer were found. Solubilities and the ternary solubility phase diagrams of N-methylephedrine enantiomers in 2 solvents [isopropanol:water, 1:3 (Vol) and (2R, 3R)-diethyl tartrate] were determined in the temperature ranges between 15°C and 25°C, and 25°C and 40°C, respectively. Preferential nucleation and crystallization experiments at higher supersaturation leading to an unusual oscillatory crystallization behavior as well as a successful preferential crystallization experiment at lower supersaturation are presented and discussed.

journal_name

J Pharm Sci

authors

Tulashie SK,Polenske D,Seidel-Morgenstern A,Lorenz H

doi

10.1016/j.xphs.2016.08.005

subject

Has Abstract

pub_date

2016-11-01 00:00:00

pages

3359-3365

issue

11

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(16)41637-0

journal_volume

105

pub_type

杂志文章
  • Inhibitory effect of valsartan on the intestinal absorption and renal excretion of bestatin in rats.

    abstract::Peptidomimetic drugs have favorable bioavailability owing to H(+)/peptide transporter 1 (PEPT1) located in the intestine. Sartans are commonly used and likely coadministered with peptidomimetic drugs in the clinic; however, in vivo interactions between sartans and peptidomimetic drugs have not been systemically unders...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23805

    authors: Huo X,Liu Q,Wang C,Meng Q,Sun H,Peng J,Ma X,Sun P,Liu K

    更新日期:2014-02-01 00:00:00

  • Prevention of molecular self-association by sodium salicylate: effect on methylene blue.

    abstract::Sodium salicylate improves the rectal absorption of drugs which exhibit molecular self-association; it is suggested that salicylate may improve drug bioavailability by altering the drug self-association pattern. Methylene blue was chosen as a model molecule for investigating the interference of salicylate with drugs u...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600750413

    authors: Touitou E,Fisher P

    更新日期:1986-04-01 00:00:00

  • Synthesis of d-pilocarpine-N-14CH3.

    abstract::The total synthesis of d-pilocarpine specifically labeled as N-14CH3 is reported. dl-Homopilopic acid was prepared as a key intermediate and resolved into the d-enantiomer via the alpha-methylbenzylamine salt. The penultimate intermediate, 2-mercaptopilocarpine, was desulfurized by oxidation with dilute hydrogen perox...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600641026

    authors: DeGraw JI,Engstrom JS,Willis E

    更新日期:1975-10-01 00:00:00

  • Nanoparticle formation of organic compounds with retained biological activity.

    abstract::Many pharmaceuticals are formulated as powders to aid drug delivery. A major problem is how to produce powders having high purity, controlled morphology, and retained bioactivity. We demonstrate the use of supercritical carbon dioxide as an antisolvent for meeting this need for two model drug systems, quercetin, a spa...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22035

    authors: Jacobson GB,Shinde R,McCullough RL,Cheng NJ,Creasman A,Beyene A,Hickerson RP,Quan C,Turner C,Kaspar RL,Contag CH,Zare RN

    更新日期:2010-06-01 00:00:00

  • Cholesterol-Targeted Anticancer and Apoptotic Effects of Anionic and Polycationic Amphiphilic Cyclodextrin Nanoparticles.

    abstract::Amphiphilic cyclodextrins (CDs) are biocompatible derivatives of natural CDs and are able to form nanoparticles or polyplexes spontaneously. In this study, nanoparticles prepared from nonionic (6OCaproβCD) or cationic amphiphilic CD (PC βCDC6) were used comparatively to develop nanoparticles intended for breast cancer...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2016.06.021

    authors: Varan G,Öncül S,Ercan A,Benito JM,Ortiz Mellet C,Bilensoy E

    更新日期:2016-10-01 00:00:00

  • A rapid HPLC method for the quantification of tyrothricin, menthol, and benzocaine in pharmaceutical formulations.

    abstract::A rapid, sensitive, and accurate reversed-phase HPLC method has been developed for the analysis and quantification of pharmaceutical formulations containing tyrothricin (1), an antibiotic used in antiseptic buccal compressed tablets for local application. The assay has been carried out under isocratic conditions, usin...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600830815

    authors: Caraballo I,Fernandez-Arevalo M,Holgado MA,Vela MT,Rabasco AM

    更新日期:1994-08-01 00:00:00

  • Modeling of the Biological Activity of Monoclonal Antibodies Based on the Glycosylation Profile.

    abstract::The influence of the glycosylation profile of IgG on biological activity is known, but it is not clear which glycoforms have the highest impact on the main mechanism of action. The aim of this study was to design a mathematical model for predicting the antibody-dependent cellular cytotoxicity (ADCC) activity and the F...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2021.01.010

    authors: Bartusik-Czubek E,Toboła P,Czubek B,Bednarek M,Balcerek J,Pietrucha T,Jaros S

    更新日期:2021-01-20 00:00:00

  • Determination of aqueous solubility and pKa values of estrogens.

    abstract::Reported estrone pKa and solubility data show wide variation. Improved experimental procedures were designed and used to obtain reproducible results. The pKa values for several estrogens and related compounds also were determined to assess the effects of structural differences on ionization. No evidence was obtained f...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600660504

    authors: Hurwitz AR,Liu ST

    更新日期:1977-05-01 00:00:00

  • Sensitive high-pressure liquid chromatographic determination of disopyramide and mono-N-dealkyldisopyramide.

    abstract::A high-pressure liquid chromatographic procedure for the accurate determination of disopyramide and its chief metabolite in plasma is presented. The method is suitable for monitoring patients receiving disopyramide therapy. A reversed-phase cyanopropylsilane column is utilized with a mobile phase of 50% acetonitrile a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600681033

    authors: Nygard G,Shelver WH,Khalil SK

    更新日期:1979-10-01 00:00:00

  • Oral apomorphine delivery from solid lipid nanoparticles with different monostearate emulsifiers: pharmacokinetic and behavioral evaluations.

    abstract::Apomorphine, a dopamine receptor agonist for treating Parkinson's disease, has very poor oral bioavailability (<2%) due to the first-pass effect. The aim of this work was to investigate whether the oral bioavailability and brain regional distribution of apomorphine could be improved by utilizing solid lipid nanopartic...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22285

    authors: Tsai MJ,Huang YB,Wu PC,Fu YS,Kao YR,Fang JY,Tsai YH

    更新日期:2011-02-01 00:00:00

  • Optimal Dosing Regimen of Phenytoin for Korean Epilepsy Patients: From Premature Babies to the Elderly.

    abstract::Phenytoin has been decreasingly used because of the high interindividual variability in drug concentration and the narrow therapeutic window. Despite such drawbacks, phenytoin is still essential as a second-line therapy for status epilepticus when patients are resistant to benzodiazepines. This study aimed to develop ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2019.03.022

    authors: Guk J,Lee SG,Chae D,Kim JH,Park K

    更新日期:2019-08-01 00:00:00

  • 2,5-Diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone II: Isolation and characterization of degradation products.

    abstract::A direct high-performance liquid chromatographic (HPLC) method was applied to monitor 2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone (I) and its degradation products in pharmaceutical vehicles at 25 +/- 0.1 degrees. At the optimal pH for stability of I, an increase in buffer concentration [phosphate and t...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600700212

    authors: Poochikian GK,Kelley JA

    更新日期:1981-02-01 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

  • Enhanced cytotoxicity of core modified chitosan based polymeric micelles for doxorubicin delivery.

    abstract::In this study, the cytotoxicity of doxorubicin (DOX) loaded stearic acid grafted chitosan oligosaccharide (CSO-SA) micelles and its core modified drug delivery systems were investigated in vitro. The in vitro drug release experiments using cellular culture medium, Roswell Park Memorial Institute 1640 (RPMI-1640) mediu...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21464

    authors: Ye YQ,Chen FY,Wu QA,Hu FQ,Du YZ,Yuan H,Yu HY

    更新日期:2009-02-01 00:00:00

  • Cholesterol as a bilayer anchor for PEGylation and targeting ligand in folate-receptor-targeted liposomes.

    abstract::Phospholipids have been extensively evaluated as an anchor for both PEGylation and receptor-targeting in liposomal formulations. However, cholesterol, another important component in biomembranes, has not been fully investigated as an alternative anchor. In this study, the potential role of cholesterol for anchoring PE...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20885

    authors: Zhao XB,Muthusamy N,Byrd JC,Lee RJ

    更新日期:2007-09-01 00:00:00

  • Amorphous stabilization and dissolution enhancement of amorphous ternary solid dispersions: combination of polymers showing drug-polymer interaction for synergistic effects.

    abstract::The purpose of this study was to understand the combined effect of two polymers showing drug-polymer interactions on amorphous stabilization and dissolution enhancement of indomethacin (IND) in amorphous ternary solid dispersions. The mechanism responsible for the enhanced stability and dissolution of IND in amorphous...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24137

    authors: Prasad D,Chauhan H,Atef E

    更新日期:2014-11-01 00:00:00

  • Solution-solubility dependency of controlled release of drug from polymer matrix: mathematical analysis.

    abstract::Two types of drug release mechanisms-matrix controlled (Q - t1/2 relationship) and partition controlled (Q - t relationship)-were reported previously. The dependency of the transition between these two processes on the solution solubility of drug is now analyzed. Mathematical expressions are derived to treat the syste...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600641011

    authors: Chien YW,Lambert HJ,Lin TK

    更新日期:1975-10-01 00:00:00

  • A sensitive high-pressure liquid chromatography/particle beam/mass spectrometry assay for the determination of all-trans-retinoic acid and 13-cis-retinoic acid in human plasma.

    abstract::A highly sensitive assay for the measurement of all-trans-retinoic acid (tretinoin) and 13-cis-retinoic acid (isotretinoin) has been developed. Collected plasma samples were protein precipitated with 2-propanol followed by solid phase extraction. The retinoic acids were subsequently derivatized to their pentafluoroben...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js950339x

    authors: Lehman PA,Franz TJ

    更新日期:1996-03-01 00:00:00

  • Kinetics and mechanism of oxidation of promazine and promethazine by ferric perchlorate.

    abstract::The equilibrium constants, kinetics, and mechanism of promazine and promethazine oxidation by ferric perchlorate were investigated at different temperatures and acidities using a stopped-flow spectrophotometric technique. The overall reaction can be represented as follows: (formula: see text) where P+ represents the r...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670212

    authors: Gasco MR,Carlotti ME

    更新日期:1978-02-01 00:00:00

  • In vitro iontophoretic studies using a synthetic membrane.

    abstract::In vitro iontophoretic administration of drugs through a microporous polyolefin membrane with hydrophilic urethane polymerfilled pores was done for the ionized drugs dexamethasone sodium phosphate, hydrocortisone sodium phosphate, and prednisolone sodium succinate, and for a nonionizable drug cortisone acetate. Curren...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600780308

    authors: Tu YH,Allen LV Jr

    更新日期:1989-03-01 00:00:00

  • Determination of salicylamide and five metabolites in biological fluids by high-performance liquid chromatography.

    abstract::Two high-performance liquid chromatographic (HPLC) assay procedures were developed for the determination of salicylamide and its metabolites in serum, urine, and saliva. One method involves reverse-phase ion-pair chromatography and UV detection, and is used to determine salicylamide, salicylamide glucuronide, and sali...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720609

    authors: Morris ME,Levy G

    更新日期:1983-06-01 00:00:00

  • Aerodynamic sizing of metered dose inhalers: an evaluation of the Andersen and Next Generation pharmaceutical impactors and their USP methods.

    abstract::The particle sizing performance of a Next Generation Pharmaceutical Impactor (NGI) was compared to that of an Andersen cascade impactor (ACI). A single lot of Vanceril MDIs containing beclomethasone dipropionate (BDP) was used throughout. MDIs were sampled into NGI and ACI in accordance with USP recommendations, at 30...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20091

    authors: Kamiya A,Sakagami M,Hindle M,Byron PR

    更新日期:2004-07-01 00:00:00

  • Major metabolites of substance P degraded by spinal synaptic membranes antagonize the behavioral response to substance P in rats.

    abstract::Substance P (SP) was degraded by synaptic membranes of rat spinal cord. Cleavage products were separated by reversed phase high performance liquid chromatography and identified by amino acid composition analyses. Major products of SP were phenylalanine, SP(1-4), SP(1-6), SP(1-7), SP(10-11), and SP(8-9). Both the degra...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js990149c

    authors: Sakurada C,Watanabe C,Sakurada S,Tan-No K,Sakurada T

    更新日期:1999-11-01 00:00:00

  • Enhanced econazole penetration into human nail by 2-n-nonyl-1,3-dioxolane.

    abstract::This study determines the enhancing effects of 2-n-nonyl-1,3-dioxolane on the penetration of econazole, an antifungal drug, into the deeper layers of the human nail where fungal infection resides. Aliquots (10 microL) of Econail lacquer formulation containing 0.45 mg of [(14)C]-econazole with 18% 2-n-nonyl-1,3-dioxola...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10291

    authors: Hui X,Chan TC,Barbadillo S,Lee C,Maibach HI,Wester RC

    更新日期:2003-01-01 00:00:00

  • Punch geometry and formulation considerations in reducing tablet friability and their effect on in vitro dissolution.

    abstract::The tablet friability resulting from formulation variations was studied under controlled granulation moisture content and tablet crushing strength. Tablets made with lactose were more friable than tablets made with microcrystalline cellulose. Replacement of 0.5% magnesium stearate with 0.5% stearic acid in the formula...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600810320

    authors: Chowhan ZT,Amaro AA,Ong JT

    更新日期:1992-03-01 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

  • Comparative stability of cephalosporins in aqueous solution: kinetics and mechanisms of degradation.

    abstract::The acidic, neutral, and alkaline degradations of six therapeutically useful cephalosporins (cephalothin, cephaloridine, cephaloglycin, cephalexin, cephradine, and cefazolin), 7-amino-cephalosporanic acid, 7-aminodeacetoxycephalosporanic acid, and some 7-substituted derivatives were followed by high-pressure liquid ch...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600651104

    authors: Yamana T,Tsuji A

    更新日期:1976-11-01 00:00:00

  • Drug delivery trends in clinical trials and translational medicine: Updated analysis of ClinicalTrials.gov database.

    abstract::While the number of clinical trials has continued to grow by about 20% in the past six months, no corresponding growth in product approval by the food and drug administration is seen or anticipated in the near future. Late-stage clinical failures due to lack of efficacy or toxicity continues to be a challenge. The opt...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21649

    authors: Ho RJ,Chien JY

    更新日期:2009-06-01 00:00:00

  • Primary Human Hepatocyte Spheroid Model as a 3D In Vitro Platform for Metabolism Studies.

    abstract::3D cultures of primary human hepatocytes (PHH) are emerging as a more in vivo-like culture system than previously available hepatic models. This work describes the characterisation of drug metabolism in 3D PHH spheroids. Spheroids were formed from three different donors of PHH and the expression and activities of impo...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.10.043

    authors: Kanebratt KP,Janefeldt A,Vilén L,Vildhede A,Samuelsson K,Milton L,Björkbom A,Persson M,Leandersson C,Andersson TB,Hilgendorf C

    更新日期:2021-01-01 00:00:00

  • Dehydration behavior of eprosartan mesylate dihydrate.

    abstract::Eprosartan mesylate (SKF 108566-J; EM) is an antihypertensive agent approved for marketing in the USA. EM dihydrate was prepared by three methods, one of which included suspending the anhydrous drug in an aqueous solution of 1.0 M methanesulfonic acid to form a slurry, followed by filtration. The dehydration kinetics ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js9900250

    authors: Sheng J,Venkatesh GM,Duddu SP,Grant DJ

    更新日期:1999-10-01 00:00:00