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PubMed1981

Idiosyncrasy to pyrazolone drugs.

Studies carried out in 68 patients with idiosyncratic reactions to noramidopyrine and/or aminophenazone led to distinction of two different groups. In the first group: 1) noramidopyrine, aminophenazone, phenylbutazone and sulfinpyrazone as well as several other inhibitors of cyclooxygenase, including aspirin, precipitated bronchoconstriction; 2) skin tests with pyrazolone drugs were virtually negative; 3) all patients had chronic asthma. In the second group: 1) noramidopyrine and aminophenazone induced anaphylactic shock and/or urticaria; 2) skin tests with these drugs were highly positive; 3) phenylbutazone, sulfinpyrazone and several other cyclooxygenase inhibitors, including aspirin, could be taken with impunity; 4) chronic bronchial asthma was present in only one-fourth of the patients. We suggest that the pathogenic mechanisms responsible for the idiosyncratic reactions involve inhibition of cyclooxygenase in the first group, and allergic reactions in the second group. Distinction of these two groups is of clinical importance since in individual patients it gives insight into the safe administration of pyrazolone and aspirin-like drugs.

Adult↗

PubMed1992

Antiinflammatory pyrazolones and pyrazolidones: a study of their inhibition of 5 beta-dihydrocortisone reduction in rat liver cytosol.

Seven pyrazolone and pyrazolidone derivates, some of them widely used as analgesic and anti-inflammatory drugs, were tested for the inhibitory property of the 3 alpha-hydroxysteroid dehydrogenase of rat liver cytosol. The data obtained clearly show that, among pyrazolone and pyrazolidone derivates, the correlation between IC50 and therapeutic potency is not always verified.

3-Hydroxysteroid Dehydrogenases↗

PubMed1981

Some novel pyrazolone derivatives as anti-inflammatory agents.

Synthesis of three series of compounds namely; 4-(phenazon-4-ylazo)-1-substituted thiocarbamoyl-3-methyl-5-pyrazolones (3-8), 4-(phenazon-4-ylazo)-1-substituted-3-methyl-5-pyrazolones (9-20) and 4-(phenazon-4-ylazo)-1-substituted-3,5-dimethylpyrazoles (21-31) was achieved. These compounds were subjected to anti-inflammatory investigation and it was found that compounds 9 and 10 exhibited a remarkable anti-inflammatory activity, of which the former was the most potent.

Animals↗

PubMed1991

Precolumn labeling of reducing carbohydrates with 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone: analysis of neutral and sialic acid-containing oligosaccharides found in glycoproteins.

A convenient precolumn labeling method was developed for the analysis of neutral and sialic acid-containing oligosaccharides in glycoproteins using 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone (PMPMP). PMPMP reacts with a reducing oligosaccharide under slightly alkaline conditions (pH 8.3) to form a 2:1 adduct (bis-PMPMP derivative). Sialic acid residues in the oligosaccharides remain intact during the reaction. Tryptic glycopeptides digested with glycopeptidase A for oligosaccharide liberation can be directly derivatized with PMPMP without prior treatment. Separation of the labeled oligosaccharides was performed by reverse-phase high-performance liquid chromatography on a C-18 column with aqueous acetonitrile, and positional isomers such as isomeric triantennary tetradecasaccharides from bovine fetuin were completely resolved. The bis-PMPMP derivatives were labile in alkaline media to form mono-PMPMP derivatives; however, the mono-PMPMP derivatives could be easily reconverted to the original bis-PMPMP derivatives. The proposed method is simpler than the reductive pyridylamination method, and detection sensitivity could reach subnanomole range with a uv detector. Oligosaccharides from ribonuclease B (bovine pancreas), ovalbumin, thyroglobulin (porcine thyroid), fetuin (bovine), and transferrin (human) have been successfully analyzed to demonstrate the usefulness of this method as an alternative to the existing methods.

Amidohydrolases↗

PubMed1993

Determination of hyaluronic acid by high-performance liquid chromatography of the oligosaccharides derived therefrom as 1-(4-methoxy)phenyl-3-methyl-5-pyrazolone derivatives.

Hyaluronic acid (HA) was digested with various kinds of depolymerizing enzymes and the products were analysed by high-performance liquid chromatography (HPLC) after derivatization with 1-(4-methoxy)phenyl-3-methyl-5-pyrazolone (PMPMP). As hyaluronate 4-glycanohydrolase (EC 3.2.1.35) from sheep testis showed a high efficiency for depolymerization, giving the tetra- and hexasaccharides abundantly, and is inexpensive, a method for the specific determination of HA was established, based on digestion by this enzyme followed by determination of the tetra- or hexasaccharide derived therefrom as the PMPMP derivatives by HPLC with UV detection. This method allowed the determination of HA in the range 0.5-50 micrograms with high reproducibility.

Animals↗

PubMed2000

Occupational asthma caused by pyrazolone derivative used in silver halide photographic paper.

Occupational asthma has been documented in workers exposed to a wide variety of chemical compounds. Reactive dyes have been described as causing occupational asthma in textile industry workers. We report a case of occupational asthma resulting from exposure to pyrazolone dye used in silver halide photographic paper. There is a need for both further surveys of workers exposed to other reactive dyes and careful preventive measures in the handling of such compounds.

Anti-Inflammatory Agents, Non-Steroidal↗

PubMedDate not supplied

[The activation of specific type-III glucocorticoid receptors by pyrazolone series preparations].

Experiments were conducted on intact and adrenalectomized male Wistar rats (weighing 180-200 g) with labelled corticosterone of high specific activity to study the effect of analgin and aminopyrine on the level of type-III glucocorticoid receptors in the liver. Analgin and aminopyrine in doses of 10(-2) and 10(-3) increase the specific binding of labelled corticosterone by type-III glucocorticoid receptors of the hepatic cytosol and by blood plasma transcortin in modelled experiments. The effect of the agents depends on the dose. Intravenous administration of 140 mg/100 g of analgin to intact rats and intraperitoneal injection of an equal dose of analgin to adrenalectomized rats also increases the specific binding of labelled corticosterone by type-III glucocorticoid receptors of the hepatic cytosol. The importance of the revealed effect of agents of the pyrazolone series in stress regulation is discussed.

Adrenalectomy↗

PubMed1986

Pyrazolone drugs and agranulocytosis.

Ever since mass consumption of chemically pure drugs started at the beginning of this century, cases of agranulocytosis have been reported in the literature. These were very soon seen as being causally related to drug use. The present paper discusses the clinical symptoms of the disease, the possibilities of its treatment, and the obvious connections between the use of pyrazolone drugs and the occurrence of agranulocytosis.

Agranulocytosis↗

PubMed1986

Pyrazolones and analgesic asthma syndrome.

Many peripherally acting analgesic and anti-inflammatory drugs, including pyrazolone derivatives, can precipitate idiosyncratic hypersensitivity reactions in intrinsic asthmatics. This contribution focuses on the symptomatology, diagnosis, and therapy ('desensitization') in childhood and adult analgesic asthma syndrome.

Adult↗

PubMed1986

Adverse dermatological reactions to pyrazolones.

All analgesics can occasionally induce adverse skin reactions. Especially in the early period of pyrazolone therapy, a large variety of cutaneous manifestations were attributed to the use of these drugs. An updated analysis is attempted.

Angioedema↗

PubMed1998

New thiazolidones-4 with pyrazolone-5 substituent as the potential NSAIDs.

The synthesis of a group of thiazolidine derivatives with pyrazolone-5 substituent is described. The structure of the new compounds is supported by 1H- and 13C-NMR spectra. Group of compounds was tested in vivo for their antiinflammatory activity. The obtained results gave the opportunity to separate the perspective groups of potential NSAIDs, which have got greater antiinflammatory activity than the best standard drugs.

Animals↗

PubMed1999

Electrospray ionization mass spectrometry of 1-phenyl-3-methyl-5-pyrazolone derivatives of neutral and N-acetylated oligosaccharides.

Derivatization using 1-phenyl-3-methyl-5-pyrazolone (PMP) was selected among a number of reported methods for labeling carbohydrates, since it gives a quantitative yield, proceeds through a rapid reaction and involves a simple clean-up procedure. Moreover, PMP derivatives provide an increase in sensitivity with ultraviolet and mass spectrometric detection relative to native neutral sugars. Sensitivity studies were carried out using a standard oligosaccharide, tetraglucose. One of the aims of these studies was to determine the minimum amounts of PMP-tetraglucose necessary to generate informative full-scan electrospray ionization (ESI) mass spectra and collision-induced dissociation tandem mass spectra. Another aim was to characterize the fragmentation pattern of PMP derivatives. Quantitative and qualitative studies were also carried out with a typical N-linked oligosaccharide obtained commercially. The PMP-labeled compound underwent directed cleavages which produced fragments containing the reducing end. The native N-linked sugar yielded fragments corresponding to cleavages from both ends of the molecule. Under the same ESI conditions, the N-linked oligosaccharide exhibited more lability, or tendency to fragment, than neutral tetraglucose, in both the derivatized and native forms. Also, PMP labeling was shown to enhance sensitivity in the case of a neutral oligosaccharide, i.e. tetraglucose, whereas the labeling of an N-acetylated oligosaccharide, NGA3, did not yield a noticeable improvement in sensitivity.

Acetylation↗

PubMed1999

Effect of 1-phenyl-3-methyl-5-pyrazolone labeling on the fragmentation behavior of asialo and sialylated N-linked glycans under electrospray ionization conditions.

The advantages of labeling free N-linked oligosaccharides with 1-phenyl-3-methyl-5-pyrazolone (PMP), for high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS) are discussed. The study focuses on some asialo and sialylated sugars, and compares the HPLC and ESI-MS behaviors of the PMP-labeled substances vs. the native compounds. It is pointed out that native free N-linked carbohydrates have very low affinities for the C18 reversed phases commonly used in HPLC. Native asialo oligosaccharides yield good ESI-MS sensitivity, although they are very susceptible to in-source collision-induced dissociation (CID), and the fragments are produced from any of the branches of the molecules, i.e. do not give specific structural information. Native N-linked standards bearing one sialic acid residue yield a 10-fold loss of ESI-MS sensitivity vs. asialo compounds, and native sugars with two sialic acid moieties were not detectable. The PMP labeling of asialo and sialylated sugars yielded higher affinities for HPLC C18 columns and, even at the early stages of method development, it was possible to separate three PMP-labeled standards to a useful extent. In ESI-MS, PMP-asialo sugars did not yield a significant increase in sensitivity vs. the native species; however, fragmentation produced by in-source CID was more directed as all predominant fragment ions contained the bis-PMP label. This feature is particularly useful when structural determination of an unknown sugar is required. PMP-sialylated sugars gave rise to very clean and informative ESI mass spectra. The monosialo sugar yielded a 100-fold sensitivity improvement vs. its native analog and, in the case of the disialylated compound, a 100% improvement was obtained in the positive mode. Most fragment ions were informative and contained the reducing end on the molecules, thus facilitating spectral interpretation. The combination of PMP derivatization with on-line HPLC/ESI-MS is a promising method for the analysis of asialo and sialylated carbohydrate mixtures.

Antipyrine↗

PubMed1998

Separation of 1-phenyl-3-methyl-5-pyrazolone derivatives of monosaccharides by capillary electrochromatography.

1-Phenyl-3-methyl-5-pyrazolone (PMP) derivatives of component monosaccharides in glycoproteins (fucose, galactose, mannose, N-acetylgalactosamine and N-acetylglucosamine) and epimeric aldopentoses (arabinose, lyxose, ribose and xylose) were well separated from each other by capillary electrochromatography on a Hypersil ODS column with a mixture of 50 mM N-(2-hydroxyethyl)piperazine-2'-(2-ethanesulfonic acid) buffer, pH 6.0 to approximately 6.3, and acetonitrile (2.2:1 v/v) as eluent. The elution of these compounds showed relatively strong dependence on the pH and concentration of the buffer salts contained in the eluent, as compared to the elution by pressure-driven high-performance liquid chromatography (HPLC) on the same stationary phase, but separation of PMP-monosaccharides was better than that by HPLC. Retention times of PMP-monosaccharides were highly reproducible with a relative standard deviation (RSD) of approximately 0.6%, and quantification with an RSD less than 5% could be achieved using 3-O-methylglucose as an internal standard.

Antipyrine↗

PubMed1997

Oligosaccharide characterization and quantitation using 1-phenyl-3-methyl-5-pyrazolone derivatization and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.

The 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of monosaccharides, maltooligosaccharides, and oligosaccharides enzymatically released from asparagine-linked sites in ribonuclease B and fetuin have been investigated using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). Use of the matrix 2,6-dihydroxyacetophenone containing diammonium hydrogen citrate (DHAP/DAHC) resulted in predominance of protonated over sodiated pseudomolecular ions of PMP-derivatized oligosaccharides. By comparison, the matrices alpha-cyano-4-hydroxycinnamic acid and 2,5-dihydroxybenzoic acid resulted in predominantly sodiated pseudomolecular ions. In addition, tendencies for fragmentation of PMP-oligosaccharide derivatives were significantly lower with DHAP/DAHC which enabled meaningful data to be obtained in reflector mode, even for samples with high excipient levels. The relative magnitude of the ion signals for PMP-derivatized maltooligosaccharides and ribonuclease B oligosaccharides correlated well with the oligomer distribution apparent by HPLC. PMP-maltohexose was used as an internal standard to quantitate PMP-oligosaccharides from ribonuclease B and asialofetuin in crude derivatization mixtures. A linear relationship was observed between the ratio of the intensities of pseudomolecualr ions and the amount of glycoprotein derivatized. The limit of detection for the major oligosaccharide of each protein was reached with ca. 3 micrograms of glycoprotein but may be further enhanced by optimization of sample handling. PMP derivatives of sialylated fetuin oligosaccharides were readily detected as protonated pseudomolecular ions by linear mode analyses. By comparison, reflector mode analyses revealed substantially reduced magnitudes of protonated pseudomolecular ions and considerable post-source fragmentation of sialic acid residues. The PMP derivatives of fetuin oligosaccharides were also amenable to exoglycosidase treatment as shown by the mass shifts found upon treatment with sialidase.

Antipyrine↗

PubMed1987

The role of descending inhibition in the antinociceptive effects of the pyrazolone derivatives, metamizol (dipyrone) and aminophenazone ("Pyramidon").

The study was carried out to provide further evidence that the two pyrazolone derivatives, metamizol and aminophenazone, produce central antinociceptive effects by stimulating inhibition descending from the periaqueductal grey (PAG) to the spinal cord. Experiments were carried out on rats in which the tail-flick response to radiant heat, nociceptive activity in ascending axons of the spinal cord, and activity of neurones in the PAG and the substantia nigra were studied. Microinjection of procaine (10 micrograms) into the PAG reduced the tail-flick latency and abolished the increase in latency caused by i.p. injection of metamizol (40 mg/kg) and aminophenazone (150 mg/kg); it did not significantly reduce the antinociceptive effect of i.p. injection of morphine (2 mg/kg). Threshold doses of morphine (1 and 2 micrograms) administered by intrathecal (i.t.) injection potentiated the effect of threshold doses of metamizol injected i.p. (10 mg/kg) or into the PAG (10 micrograms) in the tail-flick test. Morphine (2 micrograms) injected i.t. potentiated the effect of i.v. injection of metamizol (80 mg/kg) on nociceptive activity in ascending axons by eliminating the stimulant effect of metamizol on about one third of the axons. Threshold doses of morphine injected i.t. failed to potentiate the antinociceptive effect of aminophenazone (50 mg/kg) injected i.p. in the tail-flick test. The results support the view that metamizol and aminophenazone activate pathways descending from the PAG and exerting an inhibitory effect on nociceptive impulse transmission at the spinal level.

Aminopyrine↗

PubMed1988

The specificity of the lymphocyte transformation test in a patient with hypersensitivity reactions to pyrazolone compounds. A 10-week follow-up study before and after rechallenge.

To evaluate the specificity of the lymphocyte transformation test (LTT) in the diagnosis of drug allergy we studied over 71 days an atopic woman with a past history of frequent adverse reactions to pyrazolone drugs. Rechallenge with the incriminated substances aminophenazone (aminopyrine) and propyphenazone was carried out on Days 11 and 31 respectively. An immediate type of hypersensitivity reaction was seen after 100 mg aminophenazone, while 100 mg of propyphanozone led to a serum sickness-like syndrome. We found two specifically sensitized lymphocyte populations using either the pure substance or sera containing metabolite in cell cultures. Stimulatory responses with indices ranging between 3 and 6 were seen 3-4 days after exposure, and the tests remained positive in both instances for 3-4 weeks. Specific sensitization was proven by positive skin tests and by a small but distinct lymphocyte proliferative response before challenge. Several lymphocyte function tests were performed over a period of 53 days and revealed a large fall in pokeweed mitogen-induced immunoglobulin synthesis and an increase in suppressor cell activity after rechallenge with aminophenazone. We conclude that the proliferative response observed in the presence of the offending drug is due to the activation of T memory cells and therefore highly suggestive of a true allergic reaction.

Adult↗

PubMed1983

Review of the comparative analgesic efficacy of salicylates, acetaminophen, and pyrazolones.

Use of salicylates, acetaminophen, and pyrazolones has become increasingly complex, extending from the treatment of acute, mild pain to chronic, moderately severe pain. The intensity, rather than the nature, of the pain determines the efficacy of aspirin. A clinical dose-response relationship has been established, and time-effect curves indicate that the total threshold-raising effect depends on dosage frequency. Contrary to popular belief, aspirin and acetaminophen appear to be equipotent and equianalgesic for the relief of most pain. The combination of aspirin (650 mg) plus codeine (30 mg) is only slightly more effective than aspirin alone. The same holds true for acetaminophen (600 mg) plus codeine (60 mg); the efficacy of the combination is only slightly better than that of acetaminophen alone.

Acetaminophen↗