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PubMed1990

Enhancing effect of pyrrolidone derivatives on transdermal penetration of phenolsulfonphthalein and indomethacin from aqueous vehicle.

We investigated the enhancing effect of three alkyl-2-pyrrolidones on transdermal penetration of phenolsulfonphthalein (phenol red) and indomethacin from an aqueous vehicle by using an in vitro technique with excised rat skin. The enhancers included 1-methyl- (I), 1-hexyl- (II) and 1-lauryl-2-pyrrolidone (III). These derivatives effectively enhanced the penetration and skin accumulation of phenol red and indomethacin. Lipophilic enhancers such as II and III showed particularly high enhancing effects. The penetration profiles of phenol red and indomethacin showed a lag phase followed by a linear increase. Compounds II and III showed long lag times. The enhancer penetration was also determined. Compounds I and II showed a slight penetration. Compound III showed little penetration but high skin accumulation.

Animals↗
PubMed1989

Synthesis of 5-substituted 5-hydroxy-2-pyrrolidones, metabolites of the antipsychotic benzamide remoxipride.

This paper describes the synthesis of 5-[(3-bromo-2,6-dimethoxybenzamido)-methyl]-5-hydroxy-2-pyrrolidon e (3) and its 1-ethyl analogue 2, two urinary metabolites of the dopamine D-2 antagonist remoxipride [1, (S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2, 6-dimethoxybenzamide]. Two synthetic schemes leading to a common intermediate, 5-benzamido-4-oxopentanoic acid 4, were developed. This key intermediate permits conversion into either metabolite. Reaction of 4 with isobutyl chloroformate furnished a mixed carbonic anhydride, which upon treatment with ethylamine or ammonia gave the 4-oxopentanamides 5 and 6, respectively. Ring-closure afforded the corresponding 5-hydroxy-2-pyrrolidones 2 and 3.

Antipsychotic Agents↗
PubMed2004

Evaluation of exposure biomarkers from percutaneous absorption of N-methyl-2-pyrrolidone.

OBJECTIVES: The aim of this study was to evaluate different biomarkers of exposure to N-methyl-2-pyrrolidone (NMP), a widely used industrial chemical. For this purpose, differences in toxicokinetics between men and women and between pure and water-mixed NMP were evaluated after dermal absorption. METHODS: Six female and six male volunteers (groups 1 and 2) were topically exposed for 6 hours to 300 mg of NMP. An additional group of six male volunteers (group 3) was exposed to 300 mg of NMP in a 50% water solution. Blood and urine were sampled before, during, and up to 9 days after the exposure. Plasma and urine were analyzed using mass spectrometry. RESULTS: For groups 1 and 2, 16% and 18% of the applied dose were recovered in the urine as the sum of NMP and its metabolites. For group 3, 4% was recovered. The maximal concentration of 5-hydroxy-N-methyl-2-pyrrolidone (5-HNMP) was 10, 8.1, and 2.1 micromol/l for groups 1, 2 and 3, respectively, in plasma and 420, 360 and 62 micromol/l in urine adjusted for density. For 2-hydroxy-N-methylsuccinimide (2-HMSI), the maximal concentration was 5.4, 4.5, and 1.3 micromol/l for groups 1, 2 and 3, in plasma, respectively, and 110, 82 and 19 micromol/l in urine adjusted for density. For 5-HNMP there was a difference in time to reach the maximal concentration depending on whether pure NMP or 50% NMP in water was used. No such difference was seen for 2-HMSI. The differences in kinetics between male and female volunteers were small. CONCLUSIONS: Preferably 2-HMSI should be used as the biomarker of exposure to NMP.

Adult↗
PubMedDate not supplied

[Neuroprotective properties of pyroglutamic acid in combination with pyrrolidone].

A new drug composition containing pyroglutamic acid and pyrrolidone produces a significant effect on the cerebral circulation in rats with global recurrent brain ischemia and in a model ischemic state under high radial gravitational overload. In the former case, the new drug increases the blood circulation in rats with the global ischemic damage to a greater extent than in the intact control group. Pretreatment with the pyroglutamic acid--pyrrolidone composition produced a 2-2.5-fold increase in the survival of rats in the ischemic state caused by the radial gravitational overload. The data obtained show evidence of a substantial neuroprotector action of the new drug composition.

Animals↗
PubMedDate not supplied

[Characteristics of pyrrolidone pharmacokinetics in rats].

The pharmacokinetics of pyrrolidone in a composition with pyroglutamic acid was studied in white mongrel male rats. The former component exhibits cerebrovascular and neuroprotector activity. Pyrrolidone, detected in the blood plasma and brain for 8 h after peroral and intravenous administration, exhibits a high absolute bioavailability and the ability to penetrate via the blood-brain barrier.

Administration, Oral↗
PubMed1986

Density-gradient sedimentation of feline bone marrow cells with polyvinyl-pyrrolidone-coated silica gel.

Feline bone marrow cells were separated based on their density distribution in a continuous polyvinyl-pyrrolidone-coated silica gel density gradient. Morphologic identification of cytocentrifuged preparations at specific densities revealed a progressive increase in density with maturation of the cells within the granulocytic and erythroid series. Segmented eosinophils peaked at 1.084 g/ml, monocytes at 1.07 g/ml, and lymphocytes spanned the density of 1.068 to 1.084 g/ml. Bone marrow samples from 6 healthy specific-pathogen-free cats were separated by the continuous polyvinyl-pyrrolidone-coated silica gel gradient and were studied for progenitor colony formation in methylcellulose. Erythroid colony formation was greatest at a density of 1.084 g/ml and also appeared in cells from 4 cats at a lighter density of 1.016 to 1.05 g/ml. Colony formation in the granulocytic series revealed progenitors throughout the gradient with enrichment at 1.055 g/ml.

Animals↗
PubMed1979

Colorimetric determination of poly(N-vinyl-2-pyrrolidone) in contact lens solutions.

A rapid colorimetric method is presented for the quantitative determination of poly(N-vinyl-2-pyrrolidone) in contact lens solutions. The method is simple, requires no sample pretreatment, and uses only a small volume of sample. The procedure is based on the measurement of the net absorbance of a poly(N-vinyl-2-pyrrolidone)- Congo red complex at 545 nm. An accuracy of greater than +/- 4% was obtained for the concetnration ranges usually found in contact lens solutions with a minimum detection level of 10 ppm. The method is useful as a screening procedure for solutions of unknown composition and as a quality assurance procedure for routine determinations.

Colorimetry↗
PubMed1997

Major metabolic pathway for N-methyl-2-pyrrolidone in humans.

The aim was to study the metabolic pathway for N-methyl-2-pyrrolidone (NMP) in humans. Three healthy male volunteers were administered 100 mg NMP orally. All urine was collected during nine consecutive days. The identification and quantification of the metabolites were performed by gas chromatography/mass spectrometry (GC/MS). NMP, 5-hydroxy-N-methyl-2-pyrrolidone (5-HNMP), N-methylsuccinimide (MSI), and 2-hydroxy-N-methylsuccinimide (2-HMSI) were found in urine. The mean excreted fractions for NMP, 5-HNMP, MSI, and 2-HMSI were 0.8%, 44%, 0.4%, and 20%, respectively. There was no conjugation with glucoronic acid or sulfate or either 5-HNMP or 2-HMSI. One-third of the orally dosed NMP was not recovered in urine as either NMP, 5-HNMP, MSI, or 2-HMSI. The half-lives for 5-HNMP, MSI, and 2-HMSI in urine were approximately 4, 8, and 17 hr, respectively.

Administration, Oral↗
PubMed2001

Effect of chitosan-polyvinyl pyrrolidone hydrogel on proliferation and cytokine expression of endothelial cells: implications in islet immunoisolation.

Earlier we have shown the suitability of chitosan-polyvinyl pyrrolidone (PVP) hydrogel for islet immunoisolation and its inability to activate macrophages. Biomaterials that support vascularization without activating immune competent endothelial cells are desirous in islet immunoisolation. The aim of the present study was to evaluate effect of chitosan-PVP hydrogel on proliferation and activation of endothelial cells. Hydrogel did not allow the majority of cells to adhere well but maintained their viability. Hydrogel leachouts were nontoxic to the cells, as confirmed by tetrazolium reduction (MTT) and Neutral red uptake assays. Exposure to leachouts also did not alter their functionality as seen from normal expression of von Willebrand factor. 3H-thymidine incorporation revealed that hydrogel leachouts did not induce endothelial cell proliferation. Cells cultured on hydrogel and polystyrene control showed comparable expression of interleukin (IL) 6, IL-10, and transforming growth factor beta, with higher expression of tumor necrosis factor alpha as determined by reverse transcription-polymerase chain reaction. Taken together these results point out that hydrogel is compatible with endothelial cells and maintains their nonactivated status and hence is suitable as immunoisolation matrix.

Biocompatible Materials↗
PubMed2001

Optimization of DNA electrophoretic behavior in poly(vinyl pyrrolidone) sieving matrix for DNA sequencing.

Poly(vinyl pyrrolidone) solution was used as a separation matrix in capillary electrophoresis for DNA sequencing. Four-label four-color detection was performed for base calling. Dye-labeled DNA showed large mobility shifts at normal conditions for DNA separation. Temporal correction of mobility shifts was achieved by normalizing with respect to pure peaks that are without spectral interference or temporal overlap at each color channel. To achieve even better performance, a DNA separation condition that does not require corrections for mobility shifts was found. Dichlororhodamine-labeled DNA fragments showed ideal electrophoretic behaviors according to DNA size in the presence of 10 M urea. The base-calling accuracy of dichlororhodamine-labeled M13mp18 and PGEM/U DNA were 99.3% for 333 bases and 99% for 315 bases, respectively. Base calling of unknown DNA samples obtained in the presence of 10 M urea showed 99.1% accuracy.

Coloring Agents↗
PubMed2001

Rapid single nucleotide polymorphism analysis by primer extension and capillary electrophoresis using polyvinyl pyrrolidone matrix.

Rapid molecular diagnosis of 21-hydroxylase deficiency by detecting the most common mutation in the 21-hydroxylase gene is presented using primer extension and capillary electrophoresis with a polyvinyl pyrrolidone matrix. DNA samples were subjected to polymerase chain reaction (PCR) in order to amplify a 422 bp fragment of the CYP21 gene containing the single nucleotide polymorphism (SNP) site. This product served as a template in the primer extension reaction using a fluorescently labeled primer in close proximity to the SNP. ddGTP was used to block the extension if the mutation was present and the other three dNTPs to enable elongation of the primer. Fast analysis of the resulting fragments was performed by capillary electrophoresis using 10% polyvinylpyrrolidone as sieving and wall coating matrix. The Cy5-labeled primer and the two possible primer extension products (mutant and wild type) were completely separated in 90 s.

Adrenal Hyperplasia, Congenital↗
PubMed1987

[Pyrrolidone and piperidone derivatives with antihistaminic and antianaphylactic activities. Synthesis and pharmacological study].

The preparation of several derivatives to oxatomide (A), with the benzimidazolinone moiety replaced by another heterocyclic residue is described. In some cases changes to the basic chain of (A) were also considered. All the new compounds were evaluated as antihistaminics (H1) and antianaphylactics. The derivatives where the heterocyclic moiety was an unsubstituted or phenylsubstituted 2-pyrrolidone or 2-piperidone residue showed antihistaminic and antianaphylactic activities similar to those of oxatomide while modification of the basic side chain with elimination of the benzhydryl group, gave a complete loss of activity. The pharmacological screening was completed by the evaluation of the barbiturate induced sleep prolongation and of acute toxicity.

Anaphylaxis↗
PubMed2005

Radiation synthesis of poly(N-vinyl-2-pyrrolidone)-kappa-carrageenan hydrogels and their use in wound dressing applications. I. Preliminary laboratory tests.

Poly(N-vinyl-2-pyrrolidone)-kappa-carrageenan hydrogels (PVP-KC) were prepared by irradiating the mixtures of aqueous solutions of PVP, KC, potassium chloride, and poly(ethylene glycol) by gamma-rays at different doses. Their preliminary laboratory tests were evaluated to identify their usability in wound dressing applications. For investigation of the effect of components on the gelation of PVP, sol-gel analyses were made and gel fractions of the hydrogels were determined. Mechanical experiments were conducted for both unirradiated and irradiated samples. For investigation of the fluid uptake capacity of the hydrogels, swelling experiments were performed in pseudo-extracellular fluid solution at various temperatures. Acidity/alkalinity (pH) and electrical conductivity tests were achieved from aqueous extracts of hydrogels, and bioadhesion strength of the hydrogels was investigated on human skin.

Bandages↗
PubMed2005

Role of n-methyl pyrrolidone in the enhancement of aqueous phase transdermal transport.

The role of n-methyl pyrrolidone (NMP) as an enhancer for permeants delivered from an aqueous phase was investigated in the transdermal delivery of the local anesthetics lidocaine free base, lidocaine-hydrochloride (HCl), and prilocaine-HCl. Lidocaine free-base flux increased from H2O/NMP binary systems containing over 50% (v/v) NMP with significant flux enhancement observed above 80% NMP. In this range, drug flux was found to correlate with NMP flux. The addition of oleic acid (1% w/v) further enhanced lidocaine flux sixfold, in these formulations. The H2O/NMP (50% v/v) system enhanced the transport of water-soluble hydrochloride salt derivatives of lidocaine and prilocaine by factors of 4.3 and 2.6, respectively, indicating that NMP was capable of enhancing hydrophilic and hydrophobic drugs from an aqueous phase. These findings were consistent with the model that NMP flux across the stratum corneum improves the transport of formulation solutes.

Administration, Cutaneous↗
PubMed2005

Solid films of blended poly(vinyl alcohol)/poly(vinyl pyrrolidone) for topical S-nitrosoglutathione and nitric oxide release.

Nitric oxide (NO) is responsible for biological actions in mammals, ranging from the control of arterial pressure to immunological responses. In this study, S-nitrosoglutathione (GSNO), a spontaneous NO donor, was incorporated in solid films of blended poly(vinyl alcohol) (PVA) and poly(vinyl pyrrolidone) (PVP) comprising a biomaterial with potential for the local delivery of NO. In dry conditions, the extinction of the absorption bands of GSNO was correlated with the increase of the absorption band of its dimmer, GS-SG, implying NO release through the homolytic cleavage of the S-N bond. Mass spectrometry was used to confirm and to monitor the release of free NO from solid PVA/PVP-GSNO films to the gas phase. Kinetic measurement based on the Griess reaction was used to show that solid PVA/PVP-GSNO films are also capable of releasing both NO and GSNO to aqueous solution trough diffusion. Storage experiments have shown that GSNO is highly stabilized in the dry PVA/PVP matrix. The results indicate that GSNO-containing PVA/PVP films may be used for delivering free NO and/or GSNO topically and controllably.

Administration, Topical↗
PubMed1977

Stability of (pyrrolidone-5-hydroxamato)iron (III) chelates.

Overall stability constants of mono-, bis-, and tris(pyrrolidone-k-hydroxamato)iron(III) chelates were determined in aqueous solutions at 25 degrees as log beta1=1.49, log beta11=1.55, and log betaIII=0.21, respectively, where beta1=[Fe(C5H7O3N2)2+][H+]/[F=E3+][HC5H7O3N2], betaII=[Fe(C5H7O3N2)2+][H+]2/[Fe3+][hc5h7o3n2]2, and betaIII=[Fe(C5H7O3N2)3][H+]3/[Fe3+][HC5H7O3N2]3. Stability constants of all three chelates were determined potentiometrically in the 3.00-3.23 pH region. The stability constant of the mono chelate also was determined spectrophotometrically at 25 degrees as log beta1-1.52 by measuring absorbance at 500 nm (absorbance maximum), where the molar absorptivity was epsilon=1124 liters/(mole cm). Biological implications of hydroxamic acid-containing compounds are discussed.

Chemical Phenomena↗
PubMed1983

Synthesis and anticonvulsant screening of 3,3-diphenyl-2-pyrrolidone derivatives.

Six derivatives of 3,3-diphenyl-2-pyrrolidone were synthesized and screened for anticonvulsant activity. The synthetic route involved a mono-N-demethylation of an intermediate N,N-dimethylaminonitrile with methyl chloroformate followed by cleavage of the carbamate group. Of the six derivatives, (+/-)-2-imino-1,5-dimethyl-3,3-diphenylpyrrolidine hydrochloride was effective in protecting mice against maximal electroshock (MES) -induced seizures at a 30-mg/kg dose level.

Animals↗
PubMed1993

Phase diagram of (R)- and (S)-4-hydroxy-2-pyrrolidone mixtures: a new case of a conglomerate-forming system.

The phase diagram of (R)- and (S)-4-hydroxy-2-pyrrolidone presents a conglomerate in the racemic mixture. The enthalpy of melting extrapolated by the Schröder-van Laar-Le Chatelier equation [change in enthalpy (delta H) = 28410 J/mol; melting temperature (TA) = 429.9 K; solidus temperature (Ts) = 395.4 K] and the value determined by differential scanning calorimetry (delta H = 28494 J/mol; TA = 429.6 K; Ts = 394.6 K) are in excellent agreement. The experimental entropy of the mixing of enantiomers is 5.69 J/mol.K. The conglomerate nature of the racemic mixture was confirmed by X-ray and IR spectroscopy. The presence of solvates was also observed.

Calorimetry, Differential Scanning↗