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PubMed2006

Synthesis and characterization of new trimeric rhenium(I) complexes. The influence of steric factors on the size of pyrazolonaterhenium(I) metallomacrocycles.

The reaction of [ReX(CO)5] with thiosemicarbazones H2L(R) derived from beta-keto esters (X = Cl, Br; R = Me, Ph) allowed the isolation of cyclic trimeric complexes [Re3(pyz(R))3(CO)9], where pyz(R) is the pyrazolonate corresponding to the thiosemicarbazone. Electron spray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICR-MS) monitoring of the reactions of H2L(Ph) in toluene confirmed that the trimer was formed in the reaction mixture and no higher oligomer was detected. These studies, together with the X-ray structures of the trimeric complexes, afford new insight into the factors influencing the self-assembly of pyrazolonaterhenium(I) complexes.

Crystallography, X-Ray↗
PubMed1983

[Metamizol--acute overdose with suicidal intent].

An 18-year-old girl swallowed 98 tablets of Novalgin (corresponding to 49 g metamizole) with suicidal intent. After stomach lavage she received forced diuresis for 14 hours. Metamizole metabolites in serum and urine were measured by thin-layer chromatography. After 24 hours the serum concentration of metamizole metabolites was still clearly elevated. Renal elimination amounted to 11 g metamizole. The patient survived the severe overdosage without significant organ abnormalities. This favourable course differs from reports of lethal intoxication with other pyrazolone derivatives, especially those with metamizole combination drugs. The forced diuresis proved to be a satisfactory elimination procedure. Biotransformation and elimination of the metamizole metabolites still continued after 24 hours.

Adolescent↗
PubMed1984

Fixed drug eruptions. A study of 20 occurrences in Singapore.

Twenty occurrences of fixed drug eruptions (FDE) were studied. Of these, 12 were due to tetracyclines and 4 were due to analgesics (3 from pyrazolone derivatives and 1 from acetylsalicylic acid). Sixteen of the patients had less than 10 lesions each. The lips were affected in eight instances, and therefore seem preferentially involved. At presentation, seven patients were unaware of a drug relationship to their condition. A comparison of six reported series (including this one) revealed that the causative drugs varied over the years 1956-1983 as well as by region.

Adult↗
PubMed1989

Longterm prognosis of analgesic withdrawal in patients with drug-induced headaches.

We studied long-term prognosis and prognostic variables for therapeutic outcome of analgesic withdrawal in 54 patients with drug-induced headaches. The duration of headache history was 21.9 +/- 12.8 years. Each patient took an average of 38.8 +/- 22.8 tablets or suppositories a week and an average of 2.5 distinct drugs. Most patients used drugs containing several components. Caffeine was contained in at least one drug in all cases, ergotamine in 80.0% and pyrazolone in 77.1%. All patients were admitted to the hospital for two weeks. The analgesics were discontinued abruptly and the withdrawal symptoms were alleviated by neuroleptics and neurotropics. During the second week of hospital stay we started a basic therapy with calcium antagonists or beta blockers in patients suffering from migraine initially and with tricyclic antidepressants, physical therapy or biofeedback in patients suffering from tension type headaches initially. At the end of the study (mean follow-up period = 16.8 +/- 13.6 months) 38 patients (70.1%) were evaluated. 76.3% of these patients had significantly reduced their analgesic intake, 60.5% had experienced a significant relief of headache both in intensity and frequency, and 23.7% were therapeutic failures. Analysis of the time course of relapse revealed the first six months after hospital discharge as the critical period determining long-term success. The variables tested for prognostic relevance (age, sex, duration of headache history, number of tablets or suppositories taken a week, organic mental syndrome, and type of initial headaches) were not statistically significant.

Adult↗
PubMedDate not supplied

Developmental toxicity of Orange B given to rats in drinking water.

Orange B, a pyrazolone dye used to color frankfurter and sausage casings, was given in distilled drinking water to pregnant Osborne-Mendel rats throughout gestation. Assessed on the basis of fluid consumption, the dose levels of 0, 0.05, 0.1, 0.2, and 0.4% corresponded to daily Orange B consumption of 0, 67.5, 129.6, 266.6, and 532.3 mg/kg body weight, respectively. On gestation day 20, the females were euthanized and cesarean sections were performed. Throughout gestation, the treated animals consumed less fluid than did the controls, but the decreases were not dose-related. Feed consumption and maternal weight gain were not affected. No dose-related changes were seen in maternal clinical findings, implantations, fetal viability, or fetal size (weight and length). No compound-related effects were seen in sternebral development. Ossification of the interparietal bones was reduced at some dose levels, but the decreases were considered random because of absence of dose response. No dose-related effect was seen in the incidence of skeletal variations in fetuses or in the number of litters containing fetuses with skeletal variations. Skeletal development, as measured by the average number of ossified vertebrae, was similar in all groups. Soft-tissue development was not affected by dose levels of 0.05 to 0.2%. In animals treated with 0.4% Orange B, significant increases were seen in the incidence of hydroureters (severe and moderate), in the average numbers of fetuses with at least one and at least two soft-tissue variations per litter, and in the percentage of litters containing fetuses with at least two soft-tissue variations.

Administration, Oral↗
PubMed2005

[Synthesis, spectral characterization and bioactivity of complexes of furoylpyrazolone-thiosemicarbazone].

A new Schiff base containing sulphur, 1-phenyl-3-methyl-4-(alpha-furoyl) pyrazolone-5-thiosemicarbazone (HL) and its Zn(II), Cd(II) and Co(II) complexes have been synthesized. On the basis of elemental analysis and molar conductance, the general formulae of the complexes, [ZnL2] x 1.5H2O, [CdL2] x C2H5OH and [CoL2] x H2O, were given. They were characterized by IR, UV-Visible, 1H NMR, 13C NMR and magnetic moments. The results show that the metal ions exhibit coordination of six in the complexes. The antibacterial experiments indicate that they have high antibacterial activities against S. aureus, B. subtilis, E. coli, E. carotovora, and C. flaccumfaciens.

Anti-Bacterial Agents↗
PubMed2005

[Synthesis and spectral characterization of rare earth complexes of acylpyrazolone-beta-alanine].

In non-aqueous solvent, a new amino-acid schiff base, 1-phenyl-3-methyl-4-benzoyl pyrazolone-5-beta-alanine (HL) was synthesized by a reaction of beta-alanine with benzoylpyrazolone, and its ten rare earth complexes were obtained from refluxing a solution of schiff base and rare earth nitrates. On the basis of elemental analysis and molar conductance, the general formula of the complexes, [REL2NO3] nH2O (RE=La, Sm, Eu, Tb, Y, n=2; RE=Pr, Nd, n = 1; RE=Dy, Er, Yb, n=3), is given. These were characterized by IR, UV-Visible, 1H NMR, 13C NMR and fluorescence. The results show that the schiff base is a tridentate ligand, and the rare earth ions exhibit a coordination of eight in the complexes. In visible spectra, the supersensitive transitions of the Er complex at 522 nm (4 I15/2 -->2 H11/2, 4 S3/2 ) and that of the Nd complex at 573, 584 nm (4I9/2 -->2 G7/2 + 4G5/2) can be observed. Fluorescence of the complexes was produced principally by f-f transition of central ion RE3+, and the ligand has little influence on lightening role. The order of relative intensity of fluorescence of the complexes is ITb > ISm > IEu > IDy.

Alanine↗
PubMedDate not supplied

[Mucosynechial conjunctivitis and bilateral corneal ulcers in Lyell's syndrome].

The patient, aged 44, presented fever and chills with altered general condition and received an analgesic-antipyretic treatment with salicylic acid and pyrazolon derivatives. A bullous eruption that followed was labelled incipient Lyell syndrome. Both cornea presented ulcers with a tendency to perforation and mucosynechial conjunctivitis. Pathogenic Staphylococcus albus was isolated from the conjunctival secretion. The ocular phenomena improved under mydriatic treatment and trophic medication. Lyell's syndrome is the result of a severe medicamentous toxemia. Stress is laid on the role of Staphylococcus aureus, phage type 71, in the process of epidermal necrosis with detachment of the epithelium and ulceration of the mucosa.

Adult↗
PubMed1986

[Radioimmunologic detection of IgE and IgG antibodies against drugs. Conclusions after experience with over 1200 patients].

Based on the radioallergosorbent test (RAST), the authors have developed a series of assays to detect IgE and IgG antibodies against a number of frequently used drugs. In this system drugs bound covalently to cellulose paper are incubated with serum and washed; the hapten-specific IgE and IgG antibodies are then qualified and quantified by means of 125I-labelled anti-human IgE and IgG respectively. Thus far the sera of 1,228 patients have been analyzed following therapy with betalactam antibiotics, co-trimoxazole, salicylates, pyrazolones, flavonoids and tetrahydroisoquinoline. The induction of IgG antibodies is a frequent occurrence and that of IgE rare. Isolated high titers of IgE are associated mainly with anaphylactic reactions; in the presence of simultaneously raised IgG titers such side reactions are often absent. Highest IgG titers were found in patients with immune hemolysis after betalactam antibiotics, flavonoids and tetrahydroisoquinoline. In the other types of side reaction specific IgG titers were not significantly higher than in patients without side reactions. The estimation of circulating antibodies against drugs cannot yet be utilized diagnostically except in the rare cases of anaphylactic side reactions. However, the method described permits specific and sensitive detection of sensitization and is suited for scientific purposes.

Clinical Trials as Topic↗
PubMedDate not supplied

[Hemoglobin H disease. Presentation of a case].

Haemoglobin H (Hb H) disease, the most important clinical form of alpha-thalassaemia, shows remarkable clinical variability. Hb H si an unstable tetramer of beta-globin chains which accumulates because of the lack of adequate numbers of alpha-globin chains and precipitates in the red cells, causing their premature destruction. A case of Hb H disease in a 9-yr-old child, admitted into hospital for acute haemolysis after use of pyrazolone derived, is presented. Haematologic data with synthesis in vitro of globin chains were obtained from the parents and sister. The clinical and haematologic features of this form of haemoglobinopathy are briefly discussed in the light of recent knowledges of his genetic mechanism of transmission.

Anti-Inflammatory Agents↗
PubMed1984

Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom.

Nafazatrom, an antithrombotic and antimetastatic agent containing a pyrazolone functionality, is a reducing substrate for the peroxidase activity of prostaglandin H (PGH) synthase. Nafazatrom inhibits the hydroperoxide-dependent oxidation of phenylbutazone, stimulates the reduction of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, and is oxidized by microsomal or purified enzyme preparations from ram seminal vesicles. Consonant with the effects of other peroxidase-reducing substrates, nafazatrom stimulates the oxygenation of arachidonic acid to prostaglandin endoperoxides by the cyclooxygenase component of PGH synthase. In addition, nafazatrom causes an elevation in the levels of 6-keto-prostaglandin F1 alpha, the non-enzymatic hydrolysis product of prostacyclin (PGI2) biosynthesized from arachidonic acid by ram seminal vesicle microsomes. Elevation of PGI2 biosynthetic capacity by nafazatrom occurs under conditions in which prostaglandin endoperoxide biosynthesis is maximal, suggesting that nafazatrom has a stimulatory effect on the conversion of prostaglandin endoperoxides to PGI2. Nafazatrom has no effect on the ability of ram seminal vesicle microsomes to convert PGH2 to PGI2 but protects microsomal PGI2 synthase from inactivation by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid. Nafazatrom stimulates PGI2 biosynthesis in ram seminal vesicle microsomes by acting as a substrate for the peroxidase-catalyzed reduction of hydroperoxy fatty acids that are irreversible inactivators of PGI2 synthase. Several other compounds, including dipyridamole and triiodothyronine, exert similar effects. This may contribute to the reported ability of nafazatrom and related compounds to elevate the levels of bioassayable PGI2 in vivo and to the antithrombotic and antimetastatic activities of nafazatrom.

Animals↗
PubMedDate not supplied

Drug allergy: identification and characterization of IgE-reactivities to aspirin and related compounds.

Twenty-seven patients with aspirin (ASA) sensitivity were studied. 14 patients had naso-ocular-bronchial reactions after taking ASA while others had cutaneous and gastrointestinal reactions. The oral challenges with salicylic acid (SA), O-methylsalicylic acid (OMSA), ASA, and the determination of IgE antibodies specific to salicyloyl, O-methylsalicyloyl, acetylsalicyloyl using correspondent disks by RAST, RAST inhibition and RAST crossinhibition assays were performed. The findings suggest that OMSA seems to be the main offender responsible for cutaneous and gastrointestinal reactions, whereas ASA is responsible for naso-ocular-bronchial reactions. The clinical crossreactions between ASA and ASA-like drugs (nonsteroidal anti-inflammatory drugs and pyrazolone drugs) are probably due to "inborn errors of metabolism". The results indicate that genetic factors, mast-cell heterogeneity, and the interindividual variability in drug metabolism, combined with immunological background should be considered as underlying mechanisms.

Adolescent↗
PubMed1999

Synthesis of a novel series of imidazo[4,5-c]pyrazole derivatives and their evaluation as herbicidal agents.

Ever changing problems in agricultural weed control require periodic introduction of new herbicides. Imidazo[4,5-c]pyrazoles, which were considered of interest as potential herbicides, were synthesized and examined for the pre-emergence, post-emergence, and post-transplant control of weeds in rice against broadleaf and grass weed species. The data obtained suggest that some imidazo[4,5-c]pyrazoles have potential herbicidal activity against a wide range of weeds, with 5-methyl, 5-thiomethyl, and 5-unsubstituted derivatives being the most effective. No herbicidal activity was observed in the 5-methylsulfonylimidazo[4,5-c]pyrazole and imidazo[4,5-c]pyrazolone series.

Arabidopsis↗
PubMed2006

Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives.

2-(3-Hydroxy-5,5-dimethylcyclohexylidene)malononitrile 5 undergoes an azo coupling reaction with aryldiazonium salts to afford 3-amino-2-aryl-6,6-dimethyl-8-oxo-2,6,7,8-tetrahydrocinnoline-4-carbonitriles 7. Upon reflux in acetic acid, these compounds were acetylated to give the cinnoline derivatives 9. The pyrazolones 10a, b react with 3-furfurylidene- and 3-thienylidene-malononitrile derivatives 11a, b to afford the pyrano[2,3-c]pyrazole derivatives 13a-d. These newly synthesized compounds show generally a moderate molluscicidal activity to Biomphalaria alexandrina snails.

Animals↗
PubMed1998

Separation of disaccharides by affinity capillary electrophoresis in lectin-containing electrophoretic solutions.

Separation of the 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of simple disaccharides (maltose, cellobiose, gentiobiose, lactose, and melibiose) by affinity capillary electrophoresis was investigated using lectin-containing neutral phosphate buffers, filled in a linear polyacrylamide-coated capillary. When Lens culinaris agglutinin (LCA) was added, the derivatives of glucobioses were retarded with varying magnitudes depending on the amount of LCA and were well separated from each other and from galactosyl glucose under optimized conditions. Addition of Ricinus communis 60 kDa agglutinin (RCA60) to the phosphate buffer gave a different migration profile, in which the derivatives of galactosyl glucoses were more retarded than those of glucobioses. However, addition of either lectin did not accomplish complete separation of the derivatives of all these disaccharides even under optimum conditions. The addition of two kinds of lectins in appropriate proportions improved separation. Thus, the binary system composed of LCA and RCA60, as well as LCA and soybean agglutinin from Glycine max (SBA), gave better separation of these derivatives, giving peak tops for all derivatives.

Antipyrine↗
PubMed2003

Miniaturization in carbohydrate analysis.

Recent progress of microchip electrophoresis (ME) of carbohydrates is overviewed. Carbohydrate analysis by ME encounters difficulties such as lack of electric charge and deficiency of a chromophore/fluorophore in analyte molecules, however, it benefits from the accumulated knowledge of capillary electrophoresis (CE) and rapid separation of simple sugars also by ME, with high column efficiency comparable to CE, has become possible. Analysis at high pH, with electrochemical detection, is a promising approach because carbohydrates can be ionized by weak dissociation of the hydroxyl groups and the in situ formed ionic species can be effectively separated by the zone electrophoresis mode. The separated species can be sensitively monitored by electrochemical detection on a gold or copper electrode. Ionization as borate complexes and refractometric detection is also possible, though sensitivity is lower. Introduction of UV-absorbing or fluorescent tags is potentially useful but the time-consuming derivatization processes sacrifice the rapidity of ME. Examples of ME of carbohydrates as 1-phenyl-3-methyl-5-pyrazolone (PMP; for simple mono- and oligosaccharides with UV detection), 8-aminopyrene-1,3,6-trisulfonate (APTS; for oligosaccharides ladders with LIF detection), and 4-nitro-2,1,3-benzoxadiazole (NBD-F; for amino sugars and aminoalditols with LIF detection) derivatives are presented, with details of the analytical conditions. Since ME in a short separation channel enables rapid analysis within 1 min, it presents an ideal tool for clinical analysis, as shown in a few papers reporting protocols for specific blood glucose assay. Finally, the usefulness of microfluidic reactors and microarrays for enzyme-assisted carbohydrate analysis as well as glycan profiling is pointed out.

Carbohydrates↗
PubMed2004

Search for serum protein-binding disaccharides and disaccharide-binding serum proteins by affinity capillary electrophoresis.

The potential use of affinity capillary electrophoresis in a microscale search for mutually interacting substances in biological fluid is demonstrated. Some disaccharides, especially gentiobiose (Gen), derivatized with 1-phenyl-3-methyl-5-pyrazolone, caused peak retardation when electrophoresed in a neutral running buffer, containing human serum. Gen, the most significantly retarded disaccharide, was converted to its negatively charged bis-mercaptoethanesulfonate derivative (MerESGen), and a serum sample was analyzed in a neutral buffer containing the derivatized disaccharide. Two peaks, belonging to the beta-globulin fraction, were found to be remarkably retarded in the buffer containing MerES-Gen in a concentration-dependent way. These findings prove an interaction between disaccharides and serum proteins.

Beta-Globulins↗
PubMed1991

Responses of the L5178Y mouse Lymphoma cell forward mutation assay. V: 27 coded chemicals.

Twenty-seven chemicals were tested for their mutagenic potential in the L5178Y tk+/tk- mouse lymphoma cell forward mutation assay using procedures based upon those described by McGregor et al. (McGregor DB, Martin R, Cattanach P, Edwards I, McBride D, Caspary WJ (1987): Environ Mol Mutagen 9:143-160). Cultures were exposed to the chemicals for 4 hr, then cultured for 2 days before plating in soft agar with or without trifluorothymidine (TFT), 3 micrograms/ml. The chemicals were tested at least twice. Statistically significant responses were obtained with acid orange 10, aniline, benzaldehyde, o-chloroaniline, chlorodibromomethane, cytembena, 1,2-dibromo-4-(1,2-dibromomethyl) cyclohexane, dieldrin, lithocholic acid, oxytetracycline, phenazopyridine HCl, 1-phenyl-3-methyl-5-pyrazolone, sodium diethyldithiocarbamate, solvent yellow 14, tetraethylthiuram disulfide (disulfiram), 2,4-toluene diisocyanate, and 2,6-toluene diisocyanate. Apart from phenazopyridine HCl, acid orange 10, and solvent yellow 14, rat liver S9 mix was not a requirement for the mutagenic activity of these compounds. Chemical not identified as mutagens were N-4-acetylaminofluorene, chlorpheniramine maleate, chloropropamide, 1,4-dioxane, endrin, ethylene glycol, iron dextran, methapyrilene, sodium(2-ethylhexyl)alcohol

Animals↗