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PubMed2000

[Non-opioid analgesics--irreplaceable in cancer pain therapy?

Sufficient therapy of pain is essential for the treatment of tumor patients. World Health Organisation (WHO)-guidelines recommend a combination of opioids with non-opioid-analgesics (NOA) for patients with medium to strong pain. Cancer pain is often a combination of pain caused by the tumor itself, tumor associated and pain caused by therapy. Various substances act by different mechanisms and therefore combinations may demonstrate superior effects. Opioids ("central analgesics") inhibit neuronal transduction within the spinal cord, enhance inhibiting function of midbrain nuclei on ascending pain transduction and influence pain perception via modulation of the limbic system. NOAs ("peripheral analgesics") inhibit cyclooxygenase hindering activation of the peripheral nociceptor-system. There are 2 different classes of NOAs: 1) non-acidic, antipyretic analgesics like pyrazolones (metamizol) and anilin-derivates (paracetamol) and 2) non-steroidal antirheumatics (NSAR) like salicylates (acetylsalicylic acid), derivates of propionic acid (ibuprofen, naproxen), acetate acid (indomethacin, diclofenac), enolic acid (piroxicam, meloxicam) and anthranil acid (mefenamin). Adjuvant therapy is necessary to control common NSAR-side-effects like dyspepsia, ulcer and gastrointestinal bleeding. Due to its exceptional analgesic, antipyretic and spasmolytic properties, metamizol is an essential substance in tumor therapy. As agranulocytosis-incidence of 1:1,000,000 is low, good gastrointestinal and renal tolerance makes metamizol an excellent alternative to NSAR. There is scientific evidence that adequate combinations of non-opioids, opioids and adjuvant drugs, considering adverse side effects, were effective and safe in the treatment of cancer pain.

Analgesia↗
PubMed1984

Placebo application, personality, and headaches: a signal detection theory analysis of experimentally induced pain in comparison to clinical pain.

45 patients suffering from severe chronic intermittent headaches were divided into 3 groups matched for sex, and assigned to a double-blind 5-week cross-over design with 3 X 1 g/d metamizole--a mild analgesic of the pyrazolone type--a placebo, or a no-treatment control condition. For each of the 6 sessions (t0-t5) signal detection theory parameters d' and log beta for assessment of electrical pain perception and headache ratings on the preceding treatment period were obtained. At t0 all patients were examined via a personality inventory. There were no significant drug effects on headache and signal detection theory parameters, but a clear decrease of the discrimination index d' and of clinical pain over time, regardless of the mode of treatment. No relationship between pathological and experimentally induced pain could be demonstrated. There was no significant negative correlation between response bias of judgement of stimulus intensity (log beta) and neuroticism.

Adult↗
PubMed2003

Intolerance to nonsteroidal anti-inflammatory drugs might precede by years the onset of chronic urticaria.

BACKGROUND: Recent studies have found that most otherwise normal subjects with a history of acute urticaria induced by several nonsteroidal anti-inflammatory drugs (NSAIDs) show a wheal-and-flare reaction on intradermal injection of autologous serum. This phenomenon has been previously observed in patients with chronic urticaria (CU) and suggests a possible common background in CU and NSAID-induced urticaria. A relationship between these 2 conditions is further suggested by the fact that up to 30% of patients with CU have a worsening of their skin disorders after the ingestion of chemically unrelated NSAIDs. OBJECTIVE: I sought to assess whether otherwise normal subjects with multiple or single NSAID intolerance show a propensity to have CU. METHODS: Two hundred eighty otherwise normal patients with an unequivocal history of acute urticaria induced by NSAIDs seen during the last 10 years were studied. On the basis of both clinical history and oral challenge tests with at least 2 alternative NSAIDs, the patients were classified as having single or multiple NSAID intolerance. All the patients were re-evaluated within the end of 2002, 1 to 10 years after the first visit, to assess the onset of CU. One hundred allergic adults without a history of CU and of drug allergy followed up for 1 to 10 years were used as control subjects. RESULTS: One hundred fifty-nine and 121 patients were finally considered as having single or multiple NSAID intolerance, respectively. At the follow-up visit, 93 (33%) of 280 patients had CU. The prevalence of CU was very similar in subjects with single or multiple NSAID intolerance (48/159 [30%] vs 45/121 [37%], respectively; P = not significant). Only 1 (1%) of 100 atopic control subjects had CU during the follow-up period (P <.001). Among single NSAID reactors, patients who had CU had a significantly higher prevalence of intolerance to aspirin than those who did not have CU (36/48 [75%] vs 41/111 [37%], P <.001), whereas the latter had a markedly higher prevalence of intolerance to pyrazolone drugs (52/111 [47%] vs 10/48 [21%], P <.01). Altogether, only 12 (15%) of 82 patients intolerant to drugs other than aspirin versus 36 (47%) of 77 aspirin reactors had CU (P <.001). CONCLUSION: NSAID intolerance might precede the onset of CU by years. Both multiple and single NSAID reactors with a history of aspirin-induced urticaria seem at higher risk for CU than patients with a history of single intolerance to NSAIDs other than aspirin.

Adolescent↗
PubMed2004

Dipyrone overdose.

BACKGROUND: Dipyrone is a pyrazolone derivative used as an analgesic and antipyretic. Agranulocytosis, dipyrone's most serious and potentially fatal adverse effect, has led to its withdrawal in several countries. However, agranulocytosis is subject to geographical variability, ratio with at risks ranging from 0.8-23.7. In many countries dipyrone is still widely used in adults and children and even as an over-the-counter (OTC) preparation. Information on the effects of dipyrone overdose is scanty. OBJECTIVE: To determine the demographic and clinical characteristics of dipyrone overdose. METHODS: Retrospective review of prospectively collected poison center data on acute exposure to dipyrone over a three-year period. The data were subjected to descriptive analysis. Mann-Whitney test and Chi-square analysis were performed where relevant. RESULTS: A total of 243 records met the inclusion and exclusion criteria. Median age was 17y (4m-83y), median amount 5 g (250 mg-45 g), and median time to consultation was 2 h (5 min-48 h). Toxic events (49) occurred in 39 (16%) patients; 57% of these were gastrointestinal and all were mild. Time to consultation was longer in the symptomatic patients (4 h vs. 1.5 h, respectively, p=0.001) and in children (8 h vs. 3.5 h in adults). Suicidal patients ingested significantly larger amounts (8 g vs. 3.7 g, respectively, p=0.001), as did patients with gastrointestinal symptomatology (7.5 g vs. 5 g in asymptomatics, p=0.001). No agranulocytosis was reported. DISCUSSION: Dipyrone overdose is associated with mild, mainly gastrointestinal toxicity; this was noted at a median dose of 7.5 g. Early gastrointestinal decontamination may have prevented toxicity. The suggested treatment includes gastrointestinal decontamination (if <1 h since ingestion) and supportive measures.

Adolescent↗
PubMed1998

Analysis of glucuronolactone and glucuronic acid in drug formulations by high-performance liquid chromatography.

Glucuronolactone and glucuronic acid in drug formulations and beverages are determined as 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives using high-performance liquid chromatography. Intra-ester linkage (i.e., the lactone of glucuronolactone) is spontaneously hydrolyzed to free-acid form and is analyzed as the PMP derivative of glucuronic acid. By omitting three evaporation steps in the original derivatization procedure, the total analysis time is shortened to approximately 40 min. Reproducibility of determination is within 4.0% for all drug formulations. The present method satisfies the requirements for routine analysis in the quality control of drug formulations containing glucuronolactone or glucuronic acid.

Antipyrine↗
PubMed1994

Capillary electrophoresis of carbohydrates.

Capillary electrophoresis has emerged as a highly promising technique for the analysis of mono- and oligosaccharides. The approaches developed for overcoming the lack of chromophoric and fluorophoric functions in most carbohydrates involve the use of indirect photometric detection, amperometry, mass spectrometry, and precolumn derivatization with various tags. The merits and drawbacks of the derivatizing agents, including 2-aminopyridine, 4-amino-benzoic acid and its analogues, which for the first time permitted the reproducible determination of aldoses, uronic acids and even ketoses in the low femtomole range by means of readily available UV detection, and other agents such as 8-aminonaphthalene-1,3,6-trisulphonic acid, 1-phenyl-3-methyl-5-pyrazolone and 3-(4-carboxybenzoyl)-2-quinoline-carboxaldehyde, are discussed in detail. Means to secure electromigration of the usually neutral carbohydrates are: (i) ionization of hydroxyl groups at high pH; (ii) complexation of vicinal or alternate hydroxyl groups with borate or other charged compounds such as alkaline earth metal ions; (iii) derivatization with a reagent possessing ionizable functions; and (iv) partitioning into a pseudostationary phase such as sodium dodecyl sulphate micelles. Each alternative has its own analytical rewards, and combinations of the above mechanisms allow the two-dimensional and perhaps even three-dimensional mapping of oligosaccharides. Pyridylaminated oligosaccharides, for instance, have been separated both according to size by exploiting differences in the charge-to-mass ratio, with the charge being identical for each oligomer under acidic conditions due to protonation of the imino group incorporated by precolumn derivatization, as well as on the basis of structural differences, as a consequence of differences in the ease of borate complexation of the peripheral monosaccharide residues. It is also shown that the 4-aminobenzonitrile derivatives of mono- and disaccharides can be separated by micellar electrokinetic chromatography with a resolving power superior to that achieved by capillary zone electrophoresis of sugar-borate complexes. Based on the progress made, it can be concluded that capillary electrophoresis represents a powerful alternative and complement to existing methodology in the area of carbohydrate analysis.

Animals↗
PubMed1996

Agranulocytosis and near fatal sepsis due to 'Mexican aspirin' (dipyrone).

The use of "unconventional" or alternative medicine has been reported in up to one third of American households, yet only 28% report the use of such agents to their physician. We present here a case of near fatal sepsis and agranulocytosis. The agranulocytosis is attributed to the use of dipyrone (Dolo-Tiaminol), which the patient obtained in Mexico as a stronger form of generic "aspirin." The pyrazolone class of analgesics, of which dipyrone is a derivative, was introduced in the late 19th century and had a meteoric rise in use until an associated rise in fatal agranulocytosis was discovered. These agents were banned by the Food and Drug Administration (FDA) in 1977. Dipyrone is thought to induce agranulocytosis by inducing an antibody response. With the widespread use of alternative treatments, it is important for physicians to inquire as to the use of unprescribed drugs. Several resources are available to aid with the identification of foreign drugs.

Agranulocytosis↗
PubMed2000

Glycosylation of the capsid proteins of cowpea mosaic virus: a reinvestigation shows the absence of sugar residues.

The previously reported (Partridge et al., Nature 247, 391-392, 1974 ) glycosylation of the capsid proteins of cowpea mosaic virus (CPMV) has been reinvestigated. In initial studies, a preparation of purified CPMV particles was hydrolysed with HCl and amino acids and sugars were derivatized with o-phthalaldehyde (OPA). No glucosamine or galactosamine, amino sugars previously reported to occur in significant quantities in CPMV capsids, could be detected by reverse-phase high-performance liquid chromatography (RP-HPLC) of the derivatized hydrolysates. A complete analysis of all sugars potentially present was carried out by hydrolysing a sample of purified CPMV capsid proteins and derivatizing the sugars with 1-phenyl-3-methyl-5-pyrazolone. RP-HPLC analysis demonstrated that the capsids do not contain significant quantities of any sugar. The results show that, contrary to the previous report, the coat proteins of CPMV are not glycosylated.

Capsid↗
PubMed2004

Two enamines derived from 1-n-alkyl-3-methylpyrazol-5-ones.

The first two crystal structures of enamines derived from 1-n-alkyl-3-methyl-5-pyrazolones, namely 1-(n-hexyl)-3-methyl-4-[1-(phenylamino)propylidene]-2-pyrazolin-5-one, C19H27N3O, (I), and N,N'-bis[1-[1-(n-hexyl)-3-methyl-5-oxo-2-pyrazolin-4-ylidene]ethyl]hexane-1,6-diamine, C30H52N6O2, (II), are reported. The molecule of (II) lies about an inversion centre. Both (I) and (II) are stabilized by intramolecular N-H...O hydrogen bonding. This confirms previous results based on spectroscopic evidence alone.

Journal Article↗
PubMed2004

Four bromo-substituted pyrazoline and isoxazolinone spiro derivatives.

Conformational analyses and a structural comparison of the four spiro compounds 3-bromo-1,9-diphenyl-4-p-tolyl-7-oxa-1,2,8-triazaspiro[4.4]nona-2,8-dien-6-one, (I), C(24)H(18)BrN(3)O(2), 3-bromo-4-(4-methoxyphenyl)-1,9-diphenyl-7-oxa-1,2,8-triazaspiro[4.4]nona-2,8-dien-6-one, (II), C(24)H(18)BrN(3)O(3), 3-bromo-4-(4-chlorophenyl)-1,7,9-triphenyl-1,2,7,8-tetraazaspiro[4.4]nona-2,8-dien-6-one, (III), C(29)H(20)BrClN(4)O, and 3-bromo-1,7,9-triphenyl-4-p-tolyl-1,2,7,8-tetraazaspiro[4.4]nona-2,8-dien-6-one, (IV), C(30)H(22.89)Br(1.11)N(4)O, are presented. The molecular structures are rather similar, which is as expected since the compounds are all products of concerted 1,3-dipolar attack on (Z)-4-arylidene oxazolone and pyrazolone derivatives. The observed conformations tend to favour extended pi conjugation of the benzene rings and other pi systems, as shown by a comparison of selected geometric parameters of the four structures.

Journal Article↗
PubMed1980

Analgesics, allergy and asthma.

1 Recent studies of idiosyncratic reactions to analgesics have revealed several clinical patterns with a different pathogenesis. 2 In the pathogenesis of a common type of asthma precipitated by aspirin, inhibition of cyclooxygenase leading to disturbances in metabolism of arachidonic acid is of fundamental importance. 3 In some patients with urticaria/angioedema, symptoms are due to inhibition of cyclo-oxygenase by analgesics; in others the cause might be impurities in commercial preparations of aspirin; and in others the mechanisms are still unknown. 4 There is a distinct group of patients who develop anaphylactic shock or urticaria following administration of pyrazolone drugs, but who tolerate aspirin and other cyclo-oxygenase inhibitors. This type of hypersensitivity seems to have an immunological background.

Analgesics↗
PubMed1990

End-stage renal disease and non-narcotic analgesics: a case-control study.

1. To assess the risk of end-stage renal disease (ESRD) associated with the regular use of three classes of non-narcotic analgesics, we performed a case-control study of 340 patients with ESRD on a haemodialysis maintenance program and 673 hospital controls. 2. The overall odds ratio estimate for non-narcotic analgesics taken at least every other day for 30 days or longer before the first symptom of renal disease was 2.89 (95% CI, 1.78 to 4.68). 3. The risk increased in relation to the use duration. 4. The previous regular consumption of combinations containing phenacetin was strongly associated with ESRD (odds ratio, 19.05; 95% CI, 2.31 to 157.4). The odds ratio for previous regular consumption of salicylates was 2.54 (95% CI, 1.24 to 5.20) and for pyrazolones 2.16 (95% CI, 0.87 to 5.32). 5. An analysis for possible confounding by a history of repeated headaches, arthritis, kidney stones, hypertension, and diabetes did not alter the results. 6. The odds ratio estimates for different pathological subgroups of ESRD patients in relation to previous use of any non-narcotic analgesic were glomerulonephritis. 10.57 (95% CI, 1.25 to 89.0), interstitial nephritis, 3.33 (95% CI, 1.21 to 9.17), cystic kidney disease, 0.71 (95% CI, 0.25 to 1.97), and unknown, 5.15 (95% CI, 2.29-11.57). 7. The results of this study suggest that the regular consumption of analgesics should be routinely considered as a risk factor for any non-congenital cause of chronic renal failure. They also suggest that the risk of ESRD associated with the regular consumption of phenacetin is much higher than the risk associated with other non-narcotic analgesics.

Adolescent↗
PubMed2005

Oral aspirin challenges in patients with a history of intolerance to single non-steroidal anti-inflammatory drugs.

UNLABELLED: Summary Background In the clinical practice patients with a history of acute urticaria induced by a single non-steroidal anti-inflammatory drug (NSAID) and seeking for safe alternative drugs generally undergo tolerance tests with alternative NSAIDs that have little or no cyclooxygenase-1 (COX-1) enzyme inhibitory activity. This practice does not allow for the detection of single NSAID reactors and may lead to unnecessary avoidance of many potentially useful NSAIDs. OBJECTIVE: Evaluate aspirin challenge as a means to distinguish single from multiple NSAID intolerance in patients with a clinical history of acute urticaria induced by a single NSAID. Methods One hundred and seventeen otherwise normal subjects with a history of acute urticaria following the ingestion of a single NSAID (pyrazolones (n=58), nimesulide (n=17), propionic acid derivatives (n=13), aryl acetic acid derivatives (n=14), acetaminophen (n=9), piroxicam (n=5), and indometacin (n=1)) underwent single-blind placebo-controlled oral challenges with aspirin. Aspirin-intolerant subjects underwent further tolerance tests drugs exerting little or no inhibitory activity on COX-1 enzyme (including paracetamol, nimesulide, rofecoxib, tramadol, and floctafenine). Results Aspirin induced urticaria in 28/117 (24%) patients. Five out of 28 (18%) aspirin reactors did not tolerate alternative NSAID on subsequent oral challenges. Conclusion In subjects with a history of urticaria induced by a single NSAID (other than aspirin) the diagnostic workup should start with an aspirin challenge in order to detect single/multiple NSAID reactors.

Acetaminophen↗
PubMed1994

Disaccharide analysis of the skin glycosaminoglycans in patients with Werner's syndrome.

The disaccharide content of the chondroitinase-digestible glycosaminoglycans (GAGs) extracted from 6-mm skin punch biopsies from the atrophic and sclerotic skin of two patients with Werner's syndrome (WS) were determined using high-performance liquid chromatography after 1-phenyl-3-methyl-5-pyrazolone labelling. The total amount of main disaccharides was significantly decreased in the atrophic lesions of WS. In the atrophic forearm skin, the decrease in the main disaccharide unit of hyaluronic acid, delta Di-HA, and the increase in the ratio of the main disaccharide unit of dermatan sulphate, delta Di-4S, to delta Di-HA were significant vs. normal control (P < 0.01 and 0.05, respectively). The sclerotic skin showed an increase in delta Di-4S (DS) (P < 0.05) and a decrease in delta Di-HA (P < 0.02) compared with normal controls, as well as a significantly higher ratio of delta Di-4S (DS)/delta Di-HA compared with normal controls (P < 0.0002) and systemic sclerosis patients (SSc; P < 0.02). No other statistical difference was found in the amount of each main disaccharide unit between the sclerotic skin of WS and SSc. Histological examination revealed that the atrophic skin showed thinning of the dermis with a slight increase of fine collagen bundles, whereas the sclerotic skin demonstrated a thickened dermis with prominent deposition of fine collagen bundles in the deep dermis. In SSc, thickening of the whole dermis, composed of hyalinized or swollen collagen bundles, was found.(ABSTRACT TRUNCATED AT 250 WORDS)

Adult↗
PubMed1979

Fixed drug eruption: a lesson in drug usage.

Fixed drug eruption, a common finding in Lagos, was observed among patients being treated with two heavily promoted drugs: a pyrazolone analgesic and a benzodiazepine. Offending drugs should be considered in general classes rather than as individual compounds.

Adult↗
PubMed1996

The atopy trait in hypersensitivity to nonsteroidal anti-inflammatory drugs.

The prevalence of atopy was evaluated in two groups of subjects with hypersensitivity to nonsteroidal anti-inflammatory drugs (NSAID): 1) 78 patients with aspirin-induced asthma (AIA) confirmed by oral or bronchial provocation challenges 2) 42 subjects with hypersensitivity to pyrazolone drugs (case history and positive skin tests to noramidopyrine/aminophenazone) who tolerated aspirin well. Fifty sex- and age-matched persons from an unselected general population, with no hypersensitivity to NSAID, formed the control group. Atopy was estimated from the results of the following clinical and biologic parameters: 1) personal and family history of atopic diseases 2) skin prick tests with 16 aeroallergens 3) serum levels of specific IgE to five aeroallergens 4) total serum IgE level. Different definitions of atopy were used, consisting of constellations of two or three of the above-mentioned features. The results of the study revealed that the prevalence of atopy varied according to the criteria used for its definition. Irrespective of the definition used, a similar distribution of atopy was observed in both groups of patients with hypersensitivity to NSAID. Atopy was more frequent in either group of patients with intolerance of NSAID than in the control group. Thus, atopy is related to adverse drug reactions to NSAID.

Adult↗
PubMed1980

Carboxyl activation in peptide synthesis using 4-oximino-pyrazol-5-ones.

4-Oximino-pyrazol-5-ones 2a, b and their esters with N-protected amino acids 3a, b have been studied for carboxyl activation in peptide synthesis. 2a, b and 3a, b appear to be diastereoisomeric mixtures whose configurations have been assigned on the basis of spectroscopic and X-ray data. Some peptides obtained using these pyrazolone derivatives are reported: no racemization was noted by the Weigand test.

Amino Acid Sequence↗
PubMed1962

A study of possible mediators of inflammatory reactions in the mouse foot.

A number of compounds have been studied for their ability to antagonize the inflammatory reaction produced by injections of formaldehyde and 5-hydroxytryptamine in the mouse foot. An attempt has been made to elucidate the ways in which certain hydroxybenzoates, pyrazolones, sympathomimetic amines, flavone and flavanone glycosides, local anaesthetics, antihistamines and anti-5-hydroxytryptamine substances produce their anti-inflammatory effect.

Anesthetics, Local↗