On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole.

Abstract:

:Using two UV-spectrophotometric methods, the hydrolysis of tinidazole was studied at pH 1.00-8.45 at 80 degrees C. The reaction followed apparent first-order kinetics throughout the studied range. No kinetic salt effect was detected, indicating that at least one of the reacting partners forming the transition state has a charge of 0. The reaction rate macro constants M(1)-M(4) were calculated to be 3.35 x 10(-2) M(-1) h(-1), 1.45 x 10(-2) h(-1), 3.76 x 10(-6) M h(-1), and 2.85 x 10(-11) M(2) h(-1), respectively. At pH >or= 7, the uncharged tinidazole was decomposed by the hydroxide ion; the reaction was found out to involve a proton transfer from the ethylsulfonylethyl side chain. At around pH 4.5, the degradation of the uncharged tinidazole was due to the solvent. In more acidic conditions, the reaction mechanism could not be fully resolved. The alkaline hydrolysis of metronidazole was studied on the basis of literature data. A general reaction mechanism was proposed, but an unequivocal explanation for the inflection point in the pH rate profile at pH 6 could not be found. The implications of the proposed reaction mechanism for the hydrolytic behavior of ornidazole were discussed.

journal_name

J Pharm Sci

authors

Salo JP,Yli-Kauhaluoma J,Salomies H

doi

10.1002/jps.10349

subject

Has Abstract

pub_date

2003-04-01 00:00:00

pages

739-46

issue

4

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(16)31207-2

journal_volume

92

pub_type

杂志文章
  • 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

  • Improving Dissolution Properties by Polymers and Surfactants: A Case Study of Celastrol.

    abstract::Two polymorphs of celastrol were discovered and fully characterized by X-ray powder diffraction, thermogravimetry analysis, and differential scanning calorimetry. The single-crystal structures of form I and the isostructural solvate of form II were disclosed by single-crystal X-ray diffraction. The apparent solubility...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2018.07.008

    authors: Zha J,Zhang Q,Li M,Wang JR,Mei X

    更新日期:2018-11-01 00:00:00

  • Application of a variable direction hysteresis minimization approach in describing the central nervous system pharmacodynamic effects of alfentanil in rabbits.

    abstract::The relationship between the concentration of a drug and its pharmacologic effect is of central interest in pharmacodynamics. Various compartmental and noncompartmental methods have been proposed for elucidating this relationship when the plasma drug concentration and effects are both measured. Although the relationsh...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600830317

    authors: Modi NB,Veng-Pedersen P

    更新日期:1994-03-01 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

  • The Degradation Chemistry of GSK2879552: Salt Selection and Microenvironmental pH Modulation to Stabilize a Cyclopropyl Amine.

    abstract::The cyclopropyl amine moiety in GSK2879552 (1) degrades hydrolytically in high pH conditions. This degradation pathway was observed during long-term stability studies and impacted the shelf life of the drug product. This article describes the work to identify the degradation impurities, elucidate the degradation mecha...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2019.04.026

    authors: Campbell JM,Lee M,Clawson J,Kennedy-Gabb S,Bethune S,Janiga A,Kindon L,Leach KP

    更新日期:2019-09-01 00:00:00

  • Density and Shape Factor Terms in Stokes' Equation for Aerodynamic Behavior of Aerosols.

    abstract::Pharmaceutical aerosols are used to treat many pulmonary diseases. The use of low-density powders has proven useful to support efficient drug delivery. Measurements must account for the low-density, spherical particle features contributing to aerodynamic behavior. Ideally, the aerodynamic particle size distribution (A...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2017.11.005

    authors: Hickey AJ,Edwards DA

    更新日期:2018-03-01 00:00:00

  • Progestin permeation through polymer membrane V: Progesterone release from monolithic hydrogel devices.

    abstract::Progesterone release from monolithic devices prepared from various copolymers of poly(hydroxyethyl methacrylate) and poly(methoxyethoxyethyl methacrylate) or poly(methoxyethyl methacrylate) was examined. In general, plots of the fraction of drug released versus (time)1/2 were linear during the early stages of drug rel...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600700226

    authors: Song SZ,Cardinal JR,Kim SH,Kim SW

    更新日期:1981-02-01 00:00:00

  • Adapting ADME and Pharmacokinetic Analysis to the Next Generation of Therapeutic Modalities.

    abstract::The development of multiple drug modalities over the past 20 years has dramatically expanded the therapeutic space for intervention in disease processes. Rather than being alternative therapeutic approaches, these modalities tend to be complimentary both in the scope of target space and the biological mechanisms harne...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2020.09.057

    authors: Hochman JH

    更新日期:2021-01-01 00:00:00

  • Radioimmunoassay for terfenadine in human plasma.

    abstract::A radioimmunoassay procedure was developed for the antihistamine terfenadine (alpha[4-(1,2-dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol). The keto analog of terfenadine was converted to its O-carboxymethyloxime derivative, which was conjugated to bovine thyroglobulin by a mixed anhydride techniq...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600691218

    authors: Cook CE,Williams DL,Myers M,Tallent CR,Leeson GA,Okerholm RA,Wright GJ

    更新日期:1980-12-01 00:00:00

  • Confinement of Amorphous Lactose in Pores Formed Upon Co-Spray Drying With Nanoparticles.

    abstract::This study aims at investigating factors influencing humidity-induced recrystallization of amorphous lactose, produced by co-spray drying with particles of cellulose nanocrystals or sodium montmorillonite. In particular, the focus is on how the nanoparticle shape and surface properties influence the nanometer to micro...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2016.09.032

    authors: Hellrup J,Mahlin D

    更新日期:2017-01-01 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

  • Protein Nanoparticles Promote Microparticle Formation in Intravenous Immunoglobulin Solutions During Freeze-Thawing and Agitation Stresses.

    abstract::In this study, we investigated the potential roles of nanoparticles (<100 nm) and submicron (100-1000 nm) particles in the formation of microparticles (>1000 nm) in protein formulations under some pharmaceutically relevant stress conditions. Exposure of intravenous immunoglobulin solutions to the interface-associated ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2018.03.016

    authors: Pardeshi NN,Zhou C,Randolph TW,Carpenter JF

    更新日期:2018-07-01 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

  • Radiopaque liposomes: effect of formulation conditions on encapsulation efficiency.

    abstract::Liposomes containing sodium ioxitalamate were prepared by sonication. Suitable amounts of purified soybean phosphatidylcholine and cholesterol were used at various molar ratios. Stearylamine or dicetylphosphate were added to this lipid composition when charged liposomes were required. After sonication and removal of u...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600731223

    authors: Benita S,Poly PA,Puisieux F,Delattre J

    更新日期:1984-12-01 00:00:00

  • Plasma protein binding of zomepirac sodium.

    abstract::The plasma protein binding of zomepirac, a new nonnarcotic analgesic, was studied using equilibrium dialysis. Experiments were performed using human plasma and plasma from mice, rats, and rhesus monkeys, all species of pharmacological or toxicological interest. At concentrations approximating those achieved in vivo, t...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600700733

    authors: O'Neill PJ

    更新日期:1981-07-01 00:00:00

  • Protein effects on surfactant adsorption suggest the dominant mode of surfactant-mediated stabilization of protein.

    abstract::Surfactants stabilize proteins through two major mechanisms: (1) their preferential location at nearby interfaces, in this way precluding protein adsorption; and/or (2) their association with protein into "complexes" that prevent proteins from interacting with surfaces as well as each other. However, selection of surf...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23908

    authors: Kim HL,McAuley A,McGuire J

    更新日期:2014-05-01 00:00:00

  • Development of budesonide nanocluster dry powder aerosols: processing.

    abstract::Aerosolized medicine is one of the fastest growing areas in the pharmaceutical industry. Dry powder aerosols of pharmaceutical compounds are particularly attractive for the prevention and treatment of respiratory diseases but are also emerging as a treatment option for systemic diseases. Engineering particles in dry p...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23168

    authors: El-Gendy N,Selvam P,Soni P,Berkland C

    更新日期:2012-09-01 00:00:00

  • Determination of sematilide in plasma by high-performance liquid chromatography.

    abstract::A method for the determination of sematilide levels in human plasma is described. After the addition of an internal standard, plasma samples are adjusted to pH 8.5 and extracted with a solution of 7.5% isopropanol in methylene chloride. Separation from co-extracted matrix constituents is performed by reversed-phase HP...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600800214

    authors: Dancik S,Koziol T,Nisperos E,Woolf E

    更新日期:1991-02-01 00:00:00

  • The physical stability of the recombinant tuberculosis fusion antigens h1 and h56.

    abstract::The recombinant fusion proteins hybrid 1 [H1 (Ag85B-ESAT-6)] and hybrid 56 [H56 (Ag85B-ESAT-6-Rv2660c)] derived from Mycobacterium tuberculosis are promising antigens for subunit vaccines against tuberculosis. Both antigens are early batches of antigens to be enrolled in human clinical trials and it is therefore impor...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23669

    authors: Hamborg M,Kramer R,Schanté CE,Agger EM,Christensen D,Jorgensen L,Foged C,Middaugh CR

    更新日期:2013-10-01 00:00:00

  • Optimization of a Raman microscopy technique to efficiently detect amorphous-amorphous phase separation in freeze-dried protein formulations.

    abstract::A confocal Raman microscopic technique was optimized to more efficiently detect amorphous-amorphous phase separation in freeze-dried protein formulations. A Renishaw Raman inVia confocal microscope was used to collect 100-200 μm line maps (2 μm step size) of freeze-dried protein-excipient formulations. At each point a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.23882

    authors: Forney-Stevens KM,Pelletier MJ,Shalaev EY,Pikal MJ,Bogner RH

    更新日期:2014-09-01 00:00:00

  • Pharmacokinetics of mycophenolate mofetil, a new immunosuppressant, in rats.

    abstract::Mycophenolate mofetil (MPM), a new immunosuppressant, is the morpholinoethyl ester of mycophenolic acid (MPA). The distribution in blood and pharmacokinetics of MPA after administration of MPM were examined. The plasma to erythrocyte concentration ratio was low (0.10-0.15). MPA existed in rat plasma as the highly boun...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1021/js9502480

    authors: Sugioka N,Koyama H,Ohta T,Kishimoto H,Yasumura T,Takada K

    更新日期:1996-03-01 00:00:00

  • Stabilizing effect of fructose on aqueous solutions of hydrocortisone.

    abstract::Accelerated stability studies (37 degrees, 47 degrees, and 57 degrees) were conducted on buffered aqueous solutions (pH 7.4, 8.4, and 9.4) of hydrocortisone in the presence of various molar ratios of D-fructose. First-order degradation was observed. Significant improvement in hydrocortisone stability was seen in those...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600720930

    authors: Bansal NP,Holleran EM,Jarowski CI

    更新日期:1983-09-01 00:00:00

  • Cholesterol-mediated activation of P-glycoprotein: distinct effects on basal and drug-induced ATPase activities.

    abstract::Cholesterol promotes basal and verapamil-induced ATPase activity of P-glycoprotein (P-gp). We investigated whether these effects are related to each other and to the impact of the sterol on bilayer fluidity and verapamil membrane affinity. P-gp was reconstituted in egg-phosphatidylcholine (PhC) liposomes with or witho...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.21558

    authors: Belli S,Elsener PM,Wunderli-Allenspach H,Krämer SD

    更新日期:2009-05-01 00:00:00

  • Lipids, lipophilic drugs, and oral drug delivery-some emerging concepts.

    abstract::Lipid-based dose forms, which encompass a wide variety of compositional and functional characteristics, can be advantageously utilized for the formulation of lipophilic drugs. There has been a traditional reluctance to develop lipid-based dose forms due to potential problems of chemical and physical instability, and a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章,评审

    doi:10.1002/1520-6017(200008)89:8<967::aid-jps1>3.0.co

    authors: Charman WN

    更新日期:2000-08-01 00:00:00

  • Effect of low molecular weight chitosans on drug permeation through mouse skin: 1. Transdermal delivery of baicalin.

    abstract::The aim of this work was to evaluate the low molecular weight chitosans (LMWCs) as enhancers of transdermal administration of baicalin, an useful drug for the treatment of atopic dermatitis, viral hepatitis, and HIV infection. Permeation experiments were performed in vitro through mouse skin by using Franz cells. Impr...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.22063

    authors: Zhou X,Liu D,Liu H,Yang Q,Yao K,Wang X,Wang L,Yang X

    更新日期:2010-07-01 00:00:00

  • Bioavailability of erythromycin stearate: influence of food and fluid volume.

    abstract::The influence of various test meals and coadministered water volumes on erythromycin stearate bioavailability from orally dosed film-coated tablets was studied in healthy human subjects. Serum erythromycin levels were uniformly reduced by all test meals, with the reduction in mean peak serum levels varying from 47 to ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600670608

    authors: Welling PG,Huang H,Hewitt PF,Lyons LL

    更新日期:1978-06-01 00:00:00

  • Determination of propylene carbonate in pharmaceutical formulations using liquid chromatography.

    abstract::A stability-indicating reversed-phase high-performance liquid chromatographic method using a refractive index detector is described for the determination of propylene carbonate in pharmaceutical formulations. Good precision and accuracy of the method was demonstrated using an aqueous formulation. This method is also a...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.2600740626

    authors: Cheng H,Gadde RR

    更新日期:1985-06-01 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

  • Permeability of tritiated water through human cervical and vaginal tissue.

    abstract::The increased incidence of human immunodeficiency virus infection in women has identified an urgent need to develop a female-controlled method to prevent acquisition of human immunodeficiency virus and other sexually transmitted diseases. Women would apply the product intravaginally before intercourse. Development of ...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1002/jps.20107

    authors: Sassi AB,McCullough KD,Cost MR,Hillier SL,Rohan LC

    更新日期:2004-08-01 00:00:00

  • Alginate-Based Delivery Systems for Bevacizumab Local Therapy: In Vitro Structural Features and Release Properties.

    abstract::Alginate-based polyelectrolyte complexes (PECs) and hydrogel were engineered as platforms for local bevacizumab (BVZ) therapy. This study provides deep comprehension on the microstructures of such systems, and their correlation with drug-release patterns. PECs and hydrogel were characterized using Fourier transform in...

    journal_title:Journal of pharmaceutical sciences

    pub_type: 杂志文章

    doi:10.1016/j.xphs.2018.11.038

    authors: Ferreira NN,Caetano BL,Boni FI,Sousa F,Magnani M,Sarmento B,Ferreira Cury BS,Daflon Gremião MP

    更新日期:2019-04-01 00:00:00