Isomerization of ceftibuten in aqueous solution.

Abstract:

:The isomerization reactions of ceftibuten and ceftibuten-related compounds in aqueous solution were investigated to estimate the substitution effect on the isomerization reaction and identify the three proximal dissociation constants of ceftibuten kinetically from the pH-rate profiles. The isomerization reaction of ceftibuten-related compounds was influenced by the substituents near the double bond at the C7-side chain, and the electron-withdrawing substituent was found to increase the isomerization rate. Ceftibuten isomerized at the C7-side chain, and the isomerization rate was influenced by the dissociation of the C7-side chain carboxylic acid and aminothiazole in the acidic pH region. The dissociation constants of ceftibuten were assigned by comparing the isomerization rates of ceftibuten with its related compounds at various pH conditions, and the pKas 2.3, 3.2, and 4.5 were attributed to the 4-carboxylic acid, 7-carboxylic acid, and 7-aminothiazole, respectively.

journal_name

J Pharm Sci

authors

Hashimoto N,Hirano K

doi

10.1021/js980048z

subject

Has Abstract

pub_date

1998-09-01 00:00:00

pages

1091-6

issue

9

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)50637-0

journal_volume

87

pub_type

杂志文章
  • 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

  • Characterization of drug loading in crospovidone by X-ray photoelectron spectroscopy.

    abstract::The mechanism of drug loading in cross-linked polymers was studied by X-ray photoelectron spectroscopy (XPS). This gave the atomic composition of the surface layers of the loaded polymeric particles so that the exact location of the drug molecules could be identified. Three different lots of popcorn crospovidone and a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600740911

    authors: Carli F,Garbassi F

    更新日期:1985-09-01 00:00:00

  • 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 solve...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2017.12.005

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

    更新日期:2018-04-01 00:00:00

  • Dose-dependent plasma clearance of MK-826, a carbapenem antibiotic, arising from concentration-dependent plasma protein binding in rats and monkeys.

    abstract::After intravenous administration of MK-826, a new carbapenem antibiotic, the compound exhibited nonlinear pharmacokinetics in rats and monkeys. In both species, time-averaged plasma clearance (based on total concentrations) increased about 5-fold over the 10- to 180-mg/kg dose range. MK-826 was extensively plasma prot...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js980232k

    authors: Wong BK,Bruhin PJ,Lin JH

    更新日期:1999-02-01 00:00:00

  • Factorial designs in pharmaceutical stability studies.

    abstract::An approach to analyzing and interpreting kinetic data from stability studies using factorial designs is presented. This may be useful for screening purposes or as an aid in identifying significant effects in complex systems. A typical 2n factorial experiment is discussed, and methods of variance estimation and statis...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720410

    authors: Bolton S

    更新日期:1983-04-01 00:00:00

  • Adsorption of cationized bovine serum albumin onto epithelial crypt fractions of the rat colon.

    abstract::The purpose of the study was to characterize mucosal attachment of a cationized model protein, bovine serum albumin (BSA), onto the various fractions of colonic crypts epithelium in the rat. BSA was labeled with fluorescein isothiocyanate (FITC) and its surface net electric charge was modified from negative to positiv...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.1102

    authors: Blau S,Levin N,Schwartz B,Rubinstein A

    更新日期:2001-10-01 00:00:00

  • Assessing the Impact of Different Light Sources on Product Quality During Pharmaceutical Drug Product Manufacture - Fluorescent Versus Light-Emitting Diode Light.

    abstract::Pharmaceutical scientists are often asked to assess the impact of modifications to the illumination in the manufacturing and product packaging environment on product quality. To assess the impact of switching light sources, four model compounds were exposed to standard fluorescent light, LED, and "yellow light" and th...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.07.020

    authors: Wasylaschuk W,Pierce B,Geng X,Socia A,Kim D,Wuelfing WP,Abend A

    更新日期:2020-11-01 00:00:00

  • Biodegradable PLGA based nanoparticles for sustained regional lymphatic drug delivery.

    abstract::The purpose of this work is to evaluate biodegradable drug carriers with defined size, hydrophobicity, and surface charge density for preferential lymphatic uptake and retention for sustained regional drug delivery. PLGA-PMA:PLA-PEG (PP) nanoparticles of defined size and relative hydrophobicity were prepared by nanopr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21970

    authors: Rao DA,Forrest ML,Alani AW,Kwon GS,Robinson JR

    更新日期:2010-04-01 00:00:00

  • Preparation of 7,8-dimethoxy-3,4-dihydroisoquinoline, facile route to 7,8-dioxygenated-3,4-dihydroisoquinolines.

    abstract::Oxidation of 7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline with potassium permanganate in acetone afforded 7,8-dimethoxy-3,4-dihydroisoquinoline as the primary product. Hence, oxidation of the appropriate secondary nonphenolic 7,8-dioxygenated tetrahydroisoquinoline alkaloid is thus a facile method for the generation o...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600731137

    authors: el-Fishawy AM,Slatkin DJ,Knapp JE,Schiff PL Jr

    更新日期:1984-11-01 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

  • Paper chromatographic determination of chlortetracycline.

    abstract::Chlortetracycline was successfully separated from its degradation products and from other tetracyclines on a paper chromatogram previously impregnated with a mixture of edetate disodium and urea solution in pH 5.0 McIlvaine buffer. Chlortetracycline separation from its degradation products and from both tetracycline a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670432

    authors: Youssef MK,Attia IA,Safwat S

    更新日期:1978-04-01 00:00:00

  • Effect of diphenhydramine on methaqualone metabolism: an in vitro study.

    abstract::A GLC assay to quantitate the methaqualone metabolite 2-methyl-3-(2-hydroxymethylphenyl)-4(3H)-quinazolinone was developed. Standard curves were linear, and recovery of the metabolite from tissue homogenates averaged 89%. In vitro metabolism of methaqualone by the 10,000Xg supernatant fraction of rat liver homogenate ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600671114

    authors: Hindmarsh KW,Hamon NW,LeGatt DF,Wallace SM

    更新日期:1978-11-01 00:00:00

  • Synthesis, cytotoxicity, and phase-solubility study of cyclodextrin click clusters.

    abstract::To explore the possibility of cyclodextrin click clusters (CCCs) as a new cyclodextrin-based excipient, we prepared three different CCCs; heptakis{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin (HT-β-CD), heptakis{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}{2,3-di-O-methyl}-β-cyclodextrin (...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.24107

    authors: Le HT,Jeon HM,Lim CW,Kim TW

    更新日期:2014-10-01 00:00:00

  • Carfilzomib Delivery by Quinic Acid-Conjugated Nanoparticles: Discrepancy Between Tumoral Drug Accumulation and Anticancer Efficacy in a Murine 4T1 Orthotopic Breast Cancer Model.

    abstract::Despite being a major breakthrough in multiple myeloma therapy, carfilzomib (CFZ, a second-generation proteasome inhibitor drug) has been largely ineffective against solid cancer, possibly due to its pharmacokinetic drawbacks including metabolic instability. Recently, quinic acid (QA, a low-affinity ligand of selectin...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.01.008

    authors: Jun Y,Xu J,Kim H,Park JE,Jeong YS,Min JS,Yoon N,Choi JY,Yoo J,Bae SK,Chung SJ,Yeo Y,Lee W

    更新日期:2020-04-01 00:00:00

  • Interlaboratory comparison of analytical methods for residual ethylene oxide at low concentration levels in medical device materials.

    abstract::An interlaboratory comparison of two extraction methods and one thermal desorption test method for the quantification of ethylene oxide (EO) by gas chromatography in two common medical device materials, high density polyethylene (HDPE) and plasticized polyvinyl chloride (PVC), was conducted by 15 laboratories. The thr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600840524

    authors: Lao NT,Lu HT,Rego A,Kosakowski RH,Burgess DJ,Hume RD

    更新日期:1995-05-01 00:00:00

  • A novel method for determination of drug solubility in polymeric matrices.

    abstract::Crystallization of drugs in metastable, supersaturated adhesive polymeric matrices in transdermal drug delivery devices can be avoided by determination of the solubility of the drug in the adhesive polymer. A novel method is described to determine the solubility of the drug in polymeric matrices. Unlike existing metho...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20122

    authors: Jasti BR,Berner B,Zhou SL,Li X

    更新日期:2004-08-01 00:00:00

  • In vitro binding of chloroquine to rat muscle preparations.

    abstract::Chloroquine (7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline; CQ) accumulates in the insoluble fraction of rat muscle homogenates with an equilibrium distribution ratio of 7.8 L/kg. This is of a similar magnitude to muscle:plasma ratios observed in vivo. Uptake is approximately linear, even up to concentra...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600751109

    authors: MacIntyre AC,Cutler DJ

    更新日期:1986-11-01 00:00:00

  • Novel Insights to Enhance Therapeutics With Acyclovir in the Management of Herpes Simplex Encephalitis.

    abstract::Acyclovir is an antiviral drug poorly absorbed in the gastrointestinal tract due to its hydrophilicity, with low oral bioavailability (~20%). Although acyclovir is prescribed in the management of herpes simplex encephalitis (HSE), the disease has a poor prognosis, particularly if the treatment is delayed, reaching mor...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1016/j.xphs.2021.01.003

    authors: Gurgel Assis MS,Fernandes Pedrosa TC,de Moraes FS,Caldeira TG,Pereira GR,de Souza J,Ruela ALM

    更新日期:2021-01-13 00:00:00

  • Development of a nanofiltration process to improve the stability of a novel anti-MRSA carbapenem drug candidate.

    abstract::The benzenesulfonate salt of an anti-methicillin-resistant Staphylococcus aureus carbapenem antibiotic studied is a crystalline, nonhygroscopic powder which is stable at room temperature, making it an ideal compound for long-term storage. However, the limited aqueous solubility of this salt prohibits parenteral admini...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.10084

    authors: Antonucci V,Yen D,Kelly J,Crocker L,Dienemann E,Miller R,Almarrsson O

    更新日期:2002-04-01 00:00:00

  • GLC determination of (-)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo [a,d]cyclohepten-5-ylidene)piperidine in human plasma and urine.

    abstract::(-)-1-Cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo [a,d]cyclohepten-5-ylidene)piperidine (MK-160) was extracted from human plasma and urine with petroleum ether and quantitated by GLC using a nitrogen-sensitive detector. A homologue of the drug served as the internal standard. The method is specific for the d...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720725

    authors: Hucker HB,Hutt JE

    更新日期:1983-07-01 00:00:00

  • Quantitative TLC determination of propranolol in human plasma.

    abstract::A spectrodensitometric assay was developed for propranolol based on measurement of the absorbance of the drug on silica gel plates irradiated at 822 nm. Quantities as low as 0.10 microgram can be detected, and a linear relationship was obtained between 0.010 and 0.400 microgram. The percent recovery from plasma spiked...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670931

    authors: Hadzija BW,Mattocks AM

    更新日期:1978-09-01 00:00:00

  • Amino acid analogs IV:4-fluoroisoleucine.

    abstract::4-Fluoroisoleucine was produced by ammonolysis of 2-bromo-4-fluoro-3-methylpentanoic acid, which resulted from the bromofluorination of 4-methyl-2-pentenoic acid. It did not inhibit Plasmodium berghei in mice at 640 mg/kg and was not toxic to the animals. The fluoroamino acid inhibited Aspergillus niger, Trichoderma v...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670542

    authors: Gershon H,Shanks L,Clarke DD

    更新日期:1978-05-01 00:00:00

  • Expected particle size distributions of crystals produced from nonisothermal recrystallization.

    abstract::It is shown, using oxalic acid dihydrate as a model, that nonisothermal recrystallization of powders gives rise to particle size distributions which approach log-normality in many cases. The number of particles formed is, primarily, a function of the nucleation rate constants and the particle size distribution, i.e., ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600741214

    authors: Carstensen JT,Rodriguez-Hornedo N

    更新日期:1985-12-01 00:00:00

  • Quantitative structure-activity relationships and dipole moments of anticonvulsants and CNS depressants.

    abstract::The anticonvulsant and CNS-depressant activities of 16 commercially available antiepileptics were subjected to regression analysis. For the maximal electroshock seizure test and pentylenetetrazol seizure threshold test, good correlations were obtained only after diazepam, clonazepam, and carbamazepam were deleted; for...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600680418

    authors: Lien EJ,Liao RC,Shinouda HG

    更新日期:1979-04-01 00:00:00

  • Drug efflux transport properties of 2',7'-bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester (BCECF-AM) and its fluorescent free acid, BCECF.

    abstract::2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein (BCECF) is a fluorescent probe used to examine multidrug resistance-associated protein (MRP) transporter activity in cells. BCECF is introduced into the cell as the nonfluorescent membrane permeable acetoxymethyl ester, BCECF-AM, where it is hydrolyzed to the membrane ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20018

    authors: Bachmeier CJ,Trickler WJ,Miller DW

    更新日期:2004-04-01 00:00:00

  • Molecular complexing ability of quinoline and its simple derivatives.

    abstract::Electron donor-acceptor complexes for a group of quinolines and naphthalenes with 9-(dicyanomethylene)-2,4,7-trinitrofluorene in 1,2-dichloroethane were studied by optical absorption methods. Association constants, molar absorptivities, and charge-transfer transition energies were evaluated for each system, together w...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670211

    authors: Webb NE,Thompson CC

    更新日期:1978-02-01 00:00:00

  • Impact of Chemical Structure on Conjunctival Drug Permeability: Adopting Porcine Conjunctiva and Cassette Dosing for Construction of In Silico Model.

    abstract::Conjunctiva occupies most of the ocular surface area, and conjunctival permeability affects ocular and systemic drug absorption of topical ocular medications. Therefore, the aim of this study was to obtain a computational in silico model for structure-based prediction of conjunctival drug permeability. This was done b...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2017.04.061

    authors: Ramsay E,Ruponen M,Picardat T,Tengvall U,Tuomainen M,Auriola S,Toropainen E,Urtti A,Del Amo EM

    更新日期:2017-09-01 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

  • Drug release from hydrophilic matrices. 2. A mathematical model based on the polymer disentanglement concentration and the diffusion layer.

    abstract::A comprehensive model is developed to describe the swelling/dissolution behaviors and drug release from hydrophilic matrices. The major thrust of this model is to employ an important physical property of the polymer, the polymer disentanglement concentration, rho p,dis, the polymer concentration below which polymer ch...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600841214

    authors: Ju RT,Nixon PR,Patel MV,Tong DM

    更新日期:1995-12-01 00:00:00

  • Influence of pH, temperature, and buffers on the kinetics of ceftazidime degradation in aqueous solutions.

    abstract::First-order rate constants (k) were determined for the hydrolysis of ceftazidime in the pH range of 0.5 to 8.5 at 45, 55, and 65 degrees C by a stability-indicating HPLC assay. In the absence of buffer effects, the pH-rate expression was k = kH1f1(aH+) + kH2f2(aH+) + kH3f3(aH+) + kSf3 + kOHf3(aOH-), where KH and KOH a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600840504

    authors: Zhou M,Notari RE

    更新日期:1995-05-01 00:00:00