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PubMed1983

[Effect of pyrazolone derivatives on the level of reduced glutathione in rat liver].

The pyrazolone derivatives aminophenazone, phenazone, and propyphenazone are capable of decreasing reduced glutathione (GSH) in the liver after a single dose of 3 mmol/kg. The strongest effect is seen in female animals treated with propyphenazone. The depletion can be caused by (1) consumption during phase I of biotransformation, if reactive side products are inactivated by GSH-peroxidase, (2) consumption during phase II of biotransformation, if reactive metabolites are conjugated with GSH by GSH-S-transferases, (3) consumption of NADPH during the biotransformation processes of the pyrazolones as such, (4) influence on enzymes responsible for the synthesis of GSH. After repeated administration only aminophenazone decreases the hepatic content of GSH. Pretreatment with phenobarbital only prevents the propyphenazone-dependent GSH-depletion, but cobaltous chloride has no effect. GSH-depletion is regarded as one of the primary events in liver damage, following pyrazolone administration.

Aminopyrine↗

PubMed2005

The development of monocyclic pyrazolone based cytokine synthesis inhibitors.

4-Aryl-5-pyrimidyl based cytokine synthesis inhibitors that contain a novel monocyclic, pyrazolone heterocyclic core are described. Many of these inhibitors showed low nanomolar activity against LPS-induced TNF-alpha production. One of the compounds (6e) was found to be efficacious in the rat iodoacetate (RIA) in vivo model of osteoarthritis. The X-ray crystal structure of a pyrazolone inhibitor cocrystallized with mutated p38 (mp38) is presented.

Animals↗

PubMed2006

Hydroxyl radical scavenging by edaravone derivatives: Efficient scavenging by 3-methyl-1-(pyridin-2-yl)-5-pyrazolone with an intramolecular base.

We synthesized various 3-methyl-1-phenyl-5-pyrazolone (edaravone) derivatives and evaluated their oxidation potential and hydroxyl radical scavenging activity. It was found 3-methyl-1-(pyridin-2-yl)-5-pyrazolone had a much higher ability to scavenge the radical than did edaravone itself. Its efficient radical scavenging activity was assumed to be due to the increase of its anion form, an active form, by a hydrogen-bonded intramolecular base.

Antipyrine↗

PubMed2004

Synthesis and spectroscopic study on photochromism of a new thiosemicarbazone compound containing pyrazolone.

A new photochromic compound 1,3-diphenyl-4-(4'-fluro)benzal-5-pyrazolone-4-ethyl thiosemicarbazone (DP4FBP-ETSC) was synthesized by direct condensation of 1,3-diphenyl-5-pyrazolone with N4-ethyl thiosemicarbazide. The product was characterized by elemental analysis, IR and 1H NMR spectra. The photochromic properties of the compound were studied using time-dependent fluorescence emission spectra, the UV-vis reflection spectra in the solid state and the UV-vis absorption spectroscopy in liquid. The reaction rate constant of compound was also analyzed. The results show that DP4FBP-ETSC can perform photochromism.

Acetone↗

PubMed1998

Mutagenicity assay in Salmonella and in vivo sister chromatid exchange in bone marrow cells of mice for four pyrazolone derivatives.

Phenylbutazone (PB), oxyphenbutazone (OPB), antipyrine (AP) and dipyrone (DP) are four important pyrazolone derivatives mainly used as anti-inflammatory, antipyretic and analgesic drugs. At present these are the most widely used pyrazolone derivatives throughout the world. The widespread use of these drugs are of great concern for human health problems. In the present study these four drugs were tested in mutagenicity assays in Salmonella strains TA97a, TA98, TA100 and TA102 using a plate incorporation assay both with and without S-9 mix and for in vivo sister chromatid exchanges (SCE) in bone marrow cells of mice. The first three drugs were negative in all the tester strains but dipyrone showed a weak mutagenic activity at higher concentrations in all four strains both with and without metabolic activation. In the in vivo SCE assay in male mice, all four drugs showed a statistically significant increase in SCE in bone marrow cells when compared with control.

Animals↗

PubMed2003

Potentiometric, spectrometric, thermal and conductimetric studies on some 3-phenyl-4-(arylazo)-5-pyrazolones and their complexes with divalent cobalt metal ion.

3-phenyl-4-arylazo-5-pyrazolones (I-IV) have been synthesized and characterized by elemental, infrared (IR), ultraviolet and visible spectra (UV-Vis), proton nuclear magnetic resonance (1H NMR) and Mass spectra. It has been proved that these compounds exhibit a keto-enol tautomerism in solution. The donor character of the substituent increases the enol form. The ionization constants of the investigated ligands have been determined potentiometrically and found to decrease in the order OCH(3)(IV)>CH(3)(III)>H(I)>Cl(II). The Co(II) complexes of the investigated 3-phenyl-4-arylazo-5-pyrazolones (I-IV) have been prepared and characterized by elemental and thermal analyses as well as by IR, UV-Vis, electronic transition, potentiometric, conductimetric and magnetic measurements. The data suggest octahedral geometry for Co(II) (1:1) complexes and tetrahedral for Co(II) (2:3) complexes.

Cobalt↗

PubMedDate not supplied

Dimorphic exanthema manifested as reticular maculopapular exanthema and erythema multiforme major associated with pyrazolon derivatives.

The non-steroidal anti-inflammatory drugs, especially various pyrazole or pyrazolon derivatives, were one of the classes of drugs commonly implicated in erythema multiforme or Stevens-Johnson syndrome/toxic epidermal necrolysis. Reticular exanthem was a rare morphological pattern of maculopapular drug eruptions. Here we report a case of dimorphic exanthema presenting with partly reticular maculopapular exanthema and erythema multiforme-like lesions, associated with pyrazolon derivatives. Patch testing showed negative reaction to the suspected drugs. The possible mechanism underlying the association of dimorphic exanthema with NSAIDs is discussed.

Aged↗

PubMed1979

Radioimmunoassay for pyrazolone derivatives.

The determination of pyrazolone derivatives by radioimmunoassay has been reported. Anti-antipyrine antisera were obtained by repeated immunization of rabbits with 4-azoantipyrine-conjugated bovine serum albumin. The level at least as low as 1.0 ng of antipyrine could be detected by this procedure. Various substituents on the carbon 4 position of the pyrazolone ring as well as the lack of methyl group on the nitrogen 2 position decreased the affinity for the antibody, and the antibody showed no cross-reaction with any pyrazolidine derivatives.

Ampyrone↗

PubMed1987

Investigation of an alkylamine modified and pH-controlled mobile phase for separation of pyrazolone derivatives by high-performance liquid chromatography.

The separation of pyrazolone derivatives with different acid-base properties and polarities has been investigated in view of recent concepts about the retention mechanisms in reversed-phase liquid chromatography. It is shown that both the protonated (BH+) and uncharged (B) bases undergo a dual mechanism of retention due to solvophobic and silanophilic interactions. The latter are easily suppressed by the addition of an alkylamine modifier (dibutylamine) to the mobile phase. An ion-pairing mechanism is found to be valid in the retention of negatively charged (A-) pyrazolone derivatives, since the dibutylamine modifier (BH+) serves as an appropriate counter ion. The behaviour of these solutes can be predicted from the pH dependence of their capacity factors, and a new simple method is proposed for calculating the theoretical sigmoidal curves. It is shown that the elution order of the compounds can be changed by control of both the pH value and the modifier concentration in the mobile phase.

Ampyrone↗

PubMed2004

Development of orally bioavailable bicyclic pyrazolones as inhibitors of tumor necrosis factor-alpha production.

2-Aryl-3-pyrimidinyl based tumor necrosis factor-alpha (TNF-alpha) inhibitors, which contain a novel bicyclic pyrazolone core, are described. Many showed low-nanomolar activity against lipopolysaccharide-induced TNF-alpha production in monocytic cells. Secondary screening data are presented for the pyrimidinyl bicyclic pyrazolones. Several of these analogues showed good oral bioavailability in rat and efficacy in the rat iodoacetate in vivo model.

Administration, Oral↗

PubMed2002

Synthesis of spiro-fused (C5)-isoxazolino-(C4)-pyrazolones (1-oxa-2,7,8-triazaspiro[4,4]-2,8-dien-6-ones) via 1,3-dipolar cycloaddition and cycloelimination.

An efficient and selective method for the synthesis of spiro-fused (C5)-isoxazolino-(C4)-pyrazolones (C) is reported. The process consists of utilizing the Baylis-Hillman reaction-or a quicker, stepwise MAC procedure-to give I followed by 1,3-dipolar cycloaddition and Swern oxidation to give beta-ketoesters H, which were condensed with hydrazine derivatives to provide hydrazones that underwent cycloelimination. These novel spiro-fused (C5)-isoxazolino-(C4)-pyrazolones were confirmed by spectroscopic analysis as well as single-crystal X-ray of 5. We also concluded that all condensations/cycloeliminations, except with hydrazine itself, were more effective with catalysts or higher reaction temperatures. For example, TiCl(4) was an efficient catalyst for hydrazone formation and cycloelimination with methylhydrazine, while phenyl-, benzyl-, and (4-methoxyphenyl)hydrazine reacted effectively without catalyst in refluxing xylene.

Journal Article↗

PubMed2003

IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.

BACKGROUND: Propyphenazone (1,2-dihydro-1,5-dimethyl-4-(1-methylethyl)-2-phenyl-3H-pyrazol-3-one; PP) is a nonsteroidal anti-inflammatory drug frequently used as mild analgesic medicament. It belongs to the chemical group of pyrazolones. Severe adverse reactions to PP are frequent and have generally been regarded as pseudoallergic or intolerance reactions. Presently, there are no useful in vitro test systems available for the detection of antibodies directed against analgesic drugs. OBJECTIVE: The purpose of this study was to unequivocally demonstrate that IgE-mediated Type I allergy is the main mechanism leading to immediate-type adverse reactions to the analgesic drug PP. METHODS: We investigated 53 young adult patients with adverse reactions to PP. All patients developed symptoms suggestive of IgE-mediated anaphylaxis within 30 minutes after intake of a painkiller containing PP. Patients were subjected to skin tests (prick test and intracutaneous test). In addition, a novel ELISA system was developed to prove the existence of specific IgE antibodies in patients' sera. RESULTS: In 44 of 53 (83%) patients, skin tests showed typical wheal and flare reactions. Significant amounts of PP-specific serum IgE was detected in 31 of 53 (58%) of the serum samples. Moreover, in 7 of 9 patients with skin test negative results, PP-specific IgE could be detected. The assay was PP-specific because only PP, but no other pyrazolone derivative (antipyrine, aminophenazone, or metamizol), was able to inhibit IgE-binding in the system. CONCLUSION: Propyphenazone is a sensitizing agent in susceptible individuals and can elicit IgE-mediated anaphylaxis. By using skin tests and our ELISA system we were able to confirm Type I allergy in 51 of 53 (96%) patients in this study.

Adolescent↗

PubMed1980

Intoxication with pyrazolones.

1 About 50 severe or fatal (mostly accidental) cases of intoxication in children by pyrazolones have been reported in the German literature of the past 59 years. 2 Characteristic symptoms are impaired consciousness progressing to coma and convulsions. In addition, sudden apnoea and cardiac arrest may occur. Hepatic lesions may develop after a latent period of 12-24 hours. 3 Haemoperfusion seems to be the only therapeutic measure which is able to reduce the total body load of all pyrazolones to a toxicologically relevant extent. Actual clinico-toxicological data from poisoned patients are not available as yet; however, distribution volumes, plasma half-lives and endogenous plasma clearances as well as removal kinetics in vitro of aminophenazone (aminopyrine), propyphenazone, metamizole (dipyrone), phenylbutazone and oxyphenbutazone as point to the efficacy of haemoperfusion with amberlite XAD-4 resin.

Aminopyrine↗

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↗

PubMed2002

[Study of the interactions between diorganotin (IV) complexes of 1,3-dimethyl-4-acetyl-5-pyrazolone and mononucleotides and DNA].

AIM: The interactions between diorganotin (IV) complexes of 1,3-dimethyl-4-acetyl-5-pyrazolone (HL1) and mono-nucleotides together with DNA near physiological condition were investigated. METHODS: The mode of action of the diorganotin (IV) complexes with mononucleotides and DNA under different conditions and different times were investigated by high resolution NMR technology and UV spectra. RESULTS: The interaction of [(L1)2SnEt2] with AMP was shown to result in significant change of chemical shift of H(8), H(2) and 31P of AMP. Hyperchromic effect of DNA could be observed due to the interaction of; [(L1)2SnEt2] with DNA, while interaction of [(L1)2SnMe2] with AMP and DNA could only cause obvious change of chemical shift of 31P and lead to hypochromic effect of DNA. CONCLUSION: The results indicate that [(L1)2SnEt2] can selectively bind to the N1 atom of the base and the phosphate oxygen atom of AMP and may further destroy the helical structure of DNA, while the dimethyltin (IV) compound of 1,3-dimethyl-4-acetyl-5-pyrazolone [(L1)2SnMe2] merely binds to the the phosphate oxygen atom of AMP and causes the contraction of DNA helical structure.

Antineoplastic Agents↗

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↗