Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “ANTHRANILIC ACID”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 703 records · Page 39Linked to original sources

Double-blind multicenter study comparing meclofenamate sodium with indomethacin and placebo in the treatment of extra-articular rheumatic disease.

161 patients with extra-articular or non-articular disorders as acute shoulder syndrome, periarthritis humero scapularis, syndrome of the angular of the scapula, acute olecranon bursitis, acute epicondylitis and/or epitrochleitis or periarthritis of the hip were treated in this double-blind multicenter study. 53 patients received 300 mg N-(2,6-dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen) per day for a maximum of 3 weeks, 54 received 150 mg indomethacin per day and 54 received placebo. Meclofenamate sodium was significantly superior to placebo in the treatment of such symptoms as spontaneous pain, pain on motion, tenderness on pressure associated with acute episodes of extra- or non-articular rheumatism as demonstrated by earlier and superior improvement. Indomethacin showed comparable efficacy. Adverse reactions, mostly gastrointestinal symptoms, were reported by 15 patients receiving meclofenamate sodium (28.3%), 26 patients taking indomethacin (48.2%) and 5 patients in the placebo group (9.3%). The tolerance of meclofenamate sodium was good with the distinct clinical impression that meclofenamate sodium was better tolerated than indomethacin.

Adult↗

Meclofenamate sodium, phenylbutazone, and naproxen in the treatment of degenerative joint disease. Report of a placebo-controlled double-blind clinical comparison.

40 patients with definite radiographically verified degenerative joint disease of the hip and/or the knee were treated in this double-blind study. Ten patients received 300 mg N-(2,6-dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen) per day for six weeks, ten patients received 500 mg phenylbutazone per day in the first week and 300 mg per day for 5 weeks. Ten patients received 500 mg naproxen per day for 6 weeks and ten patients received placebo. Measurements to assess efficacy were: intensity of pain on passive motion, intensity of starting pain, extent of painfree abduction (if the hip was involved), maximum extension and flexion (if the knee was involved) and an overall rating of the patient's condition by both the physician and the patient. Analysis of the results demonstrated that meclofenamate sodium was significantly superior to placebo in relieving pain and improving articular function as well as in improving the overall condition in patients with degenerative joint disease of the knee and/or the hip. Phenylbutazone and naproxen showed comparable statistically significant efficacy. Although the differences between the three active drug groups at the end of treatment were statistically not significant, it was, however, of interest that they favored meclofenamate sodium in each measurement, so that the 3 active agents may be ranked as follows: 1. meclofenamate sodium; 2. phenylbutazone; 3. naproxen. Meclofenamate sodium was well tolerated as were the other active drugs. Six of the 10 patients in the phenylbutazone group exhibited a marked decrease of the WBC count at the end of treatment.

Adult↗

Meclofenamate sodium in the treatment of degenerative joint disease of the hand (Heberden nodes).

41 patients with radiographically verified degenerative joint disease of the hand who had at least one acutely inflamed Heberden node entered into the study. 22 patients were treated with 300 mg N-(2,6-dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen) per day for 4 weeks and 19 patients received placebo. Measures of efficacy were: the number of painful joints on both hands, an index of pain, the number of inflamed Heberden nodes and the grip strength (mmHg). Disease activity was similar in both groups at the beginning of the study. Analyses after one week of treatment and at the last observation at the conclusion of the study revealed significant differences in favor of meclofenamate sodium. This indicates that meclofenamate sodium treatment of degenerative joint disease of the hands is significantly superior to placebo. The reduction of the number of inflamed Heberden nodes demonstrates the anti-inflammatory effect of meclofenamate sodium, while the reduction of painful joints and the decreased pain index is evidence of the analgesic effect of this drug. The increase in grip strength indicates an improvement of function. The results further demonstrate the early onset of treatment effect with meclofenamate sodium. Meclofenamate sodium was well tolerated.

Adult↗

Meclofenamate sodium in the treatment of ankylosing spondylitis. Report of a European double-blind controlled multicenter study.

98 patients with reversible, definite, active ankylosing spondylitis were selected for this study. 49 patients were treated with N-(2,6-dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen) and 49 patients with indometacin. Following a single-blind baseline period on placebo, patients received either 200 mg meclofenamate sodium per day or 100 mg indometacin per day for one week, in the second week the doses were increased to 250 mg meclofenamate sodium and 125 mg indometacin and from the third through the eight week 300 mg meclofenamate sodium and 150 mg indometacin were given. The results of this double-blind study showed that similar improvement in mobility of the vertebral column and spondylitic pain could be achieved with meclofenamate sodium and indometacin in patients with ankylosing spondylitis. Although both treatments were well tolerated fewer meclofenamate sodium patients reported adverse reactions than did those who had received indometacin. It is concluded that meclofenamate sodium offers an effective and safe alternative to indometacin in the treatment of patients with ankylosing spondylitis.

Adolescent↗

Meclofenamate sodium in the treatment of post-traumatic edema. Report of a controlled double-blind study.

130 patients with edema as the sequel of a traumatic incident were selected for this study, 43 patients were treated with 300 mg N-(2,6-dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen) per day for one week, 44 patients received 600 mg oxyphenbutazone per day and 43 patients received placebo. Medication could be terminated if edema and pain disappeared or if deterioration or intolerance occurred. Extent of edema and degree of pain were assessed at entry into the study and on days 3, 5 and 8. Efficacy was assessed by the number of days elapsed before definite reduction and/or complete disappearance of edema and by the decrease and disappearance of pain. Meclofenamate sodium proved to be significantly superior to placebo in the treatment of patients with post-traumatic edema and post-traumatic pain. Reduction and disappearance of edema and cessation of pain occurred significantly more promptly in patients receiving meclofenamate sodium than in those receiving placebo. Although no statistically significant differences were observed between meclofenamate sodium and oxyphenbutazone, the results suggested that meclofenamate sodium might be clinically superior. Meclofenamate sodium was well tolerated.

Adolescent↗

On the mechanism of the pharmacologic activity of meclofenamate sodium.

N-(2,6-Dichloro-m-tolyl)anthranilic acid, sodium salt (meclofenamate sodium, Meclomen), the sodium salt of meclofenamic acid, has anti-inflammatory activity both in animal models and in clinical use. This activity is believed to be due in large part to the ability of the drug to inhibit the synthesis of prostaglandins by inhibiting arachidonic acid cyclo-oxygenase. Further, there is evidence that meclofenamic acid directly antagonizes the actions of prostaglandins at receptor sites. In addition, meclofenamic acid may also inhibit arachidonic acid lipoxygenase, resulting in decreased synthesis of leukotrienes, known mediators involved in the inflammatory process.

Animals↗

Synthesis of auxins from tryptophan and tryptophan-precursors by fungi isolated from mycorrhizae of pine (Pinus silvestris L.).

Fungi isolated from mycorrhizae of pine required tryptophan for auxin synthesis. More auxins were found in culture grown with pyrogallol than in those without this compound. The fungi studied produced also auxins from other than tryptophan compounds. Indole employed with serine was more suitable for the production of auxins than indole or anthranilic acid used separately. The active compounds showing auxin activity were located on the chromatograms at Rf 0.2--0.4 and 0.3--0.5 with the solvent system isopropanol, ammonia, water (10:1:1 v/v).

Culture Media↗

Strain differences in the tryptophan metabolite excretion and enzyme activities along the kynurenine pathway in rats.

The strain differences of the urinary excretion of the tryptophan metabolites along the kynurenine pathway and the variations of enzyme activities metabolizing the tryptophan have been studied in different strains of rats. There is a good correlation between urinary excretory values of the metabolites and enzyme activities in the same strain of rats. However, some differences appear when the data are compared among different strains. Wistar, heterozygous Gunn and Sprague-Dawley rats show similar total urinary excretion of tryptophan metabolites, while the Long Evans rats have significantly lower values, in accordance with the lower activity of tryptophan pyrrolase. Kynureninase activity is slightly but not significantly higher in Sprague-Dawley rats, in agreement with the high levels of anthranilic acid excreted. As regards kynurenine aminotransferase, Sprague-Dawley rats show lower activity in the liver, but higher activity in the kidneys in comparison to other strains of Wistar, Long Evans and heterozygous Gunn rats. The importance of considering strain differences is emphasized when making comparisons of measurements carried out in different laboratories.

Animals↗

Neurospora crassa glutamine synthetase. Purification by affinity chromatography and characterization of subunit structure.

Neurospora crassa glutamine synthetase was purified to homogeneity by a procedure based on affinity chromatography. The enzyme is adsorbed to a matrix of anthranilic acid bound to Sepharose and eluted with AMP. Different experimental approaches indicate that the enzyme has an octameric structure formed by subunits of identical molecular weight.

Chromatography, Affinity↗

Glaphenine-containing gallstones.

Glaphenine is an analgesic drug derived from anthranilic acid. We report the analytical procedures for stone analysis in three cases of common bile duct stones containing glaphenic acid, which developed in arthrosic patients treated for 13.7 +/- 5 years with glaphenine. Stone analysis was performed by infrared spectroscopy, high performance thin layer chromatography, scanning electron microscopy and energy dispersive X-ray analysis. Mechanisms of lithogenesis are discussed. These observations emphasize the possibility of radiolucent gallstones mainly composed of drug compounds.

Aged↗

Mechanisms of bradykinin-induced insulin secretion in clonal beta cell line RINm5F.

We investigated the mechanisms underlying bradykinin (BK)-induced rise in intracellular Ca++ concentration [Ca++]i and insulin secretion using clonal beta cell line RINm5F. Incubation with a range of concentrations of BK increased in concentration-dependent manners both insulin secretion (BK of 10 nM to 10 microM) and [Ca++]i (BK of 100 nM to 100 microM). In Ca++-containing medium, BK (1 microM) induced a biphasic [Ca++]i rise, which was characterized by a Ca++ peak and a sustained Ca++ phase. In the Ca++-free medium, BK failed to increase insulin secretion and induced only a Ca++ peak without the sustained Ca++ phase. Thapsigargin (1 microM), an inhibitor of the Ca++ pump in the endoplasmic reticulum, abolished the Ca++ peak and the sustained phase. Nimodipine (1 microM), a voltage-dependent Ca++ channel blocker, abolished the BK-induced sustained Ca++ phase and inhibited BK-induced insulin release. The BK1 receptor agonist des-Arg9-BK (1 microM) did not change either [Ca++]i or insulin secretion. Both the BK-induced insulin secretion and rise in [Ca++]i were inhibited by a selective BK2 receptor antagonist, HOE 140 (3.3-100 nM), in concentration-dependent manners but were not by a BK1 receptor antagonist des-Arg9,Leu8-BK (1 microM). Pretreatment with pertussis toxin (0.1 microg/ml) did not block the BK-induced insulin secretion or increase in [Ca++]i. U-73122 (4, 6 and 8 microM), a phospholipase C inhibitor, antagonized both the BK-induced insulin secretion and the increase in [Ca++]i in a concentration-dependent and parallel manner. BK increased intracellular concentrations of inositol-1,4,5-trisphosphate (IP3). Neither (p-amylcinnamoyl)anthranilic acid (100 microM), a phospholipase A2 inhibitor, nor N(G)-nitro-L-arginine methylester (100 microM), a nitric oxide synthase inhibitor, inhibited these effects of BK. Taken together, these findings suggested that in beta cells, BK activates BK2 receptors, which, in turn, activate a pertussis toxin-insensitive G protein. The G protein couples to phospholipase C, which promotes the formation of IP3 and diacylglycerol. IP3 releases [Ca++]i from the intracellular Ca++ store, probably the endoplasmic reticulum, which triggers Ca++ influx via voltage-dependent Ca++ channels and thus increases insulin secretion.

Bradykinin↗

Purification, subunit structure and partial amino-acid sequence of anthranilate-5-phosphoribosylpyrophosphate phosphoribosyltransferase from the enteric bacterium Serratia marcescens.

The enzyme anthranilate-5-phosphoribosylpyrophosphate phosphoribosyltransferase from Serratia marcescens was purified to apparent homogeneity. The purification procedure included ammonium sulfate precipitation, DEAE-cellulose chromatography, Sephadex gel filtration and hydroxyapatite chromatography. The molecular weight of the native protein as determined on a calibrated Sephadex G-200 column was 45000. Dodecylsulfate-polyacrylamide gel electrophoresis in the presence of reducing agent revealed a subunit molecular weight of 43000 +/- 900, suggesting that the enzyme exists as a monomer. The sequence of the amino-terminal 38 residues revealed that three amino amino acids, glutamine (six residues), glutamic acid (five residues) and serine (five residues) comprised 42% of the sequence composition.

Amino Acid Sequence↗

Polar and antipolar mutants in the tryptophan operon of Salmonella typhimurium.

Polar mutations in trpA, the first structural gene of the tryptophan operon of Salmonella typhimurium, have an uncoordinate effect on the expression of the distal genes, with trpB, the second gene, being more drastically affected than the last three. A number of these polar mutant strains grow very poorly on anthranilic acid-supplemented minimal medium. By selecting for more rapid growth in the presence of anthranilic acid, secondary mutant clones showing a correction of the polar effect were isolated. A few of these were analyzed and shown to contain deletions of various segments of the trpA gene. Ten randomly isolated deletion mutants missing various segments of the trp operon were analyzed for possible pleiotropic effects. Five of them showed a pleiotropic effect of some sort and five did not. Of those showing pleiotropic effects, one had lost the promotor-like elements necessary to initiate expression of the operon, three showed possible antipolar effects, and one showed both polar and antipolar effects simultaneously.

Genes↗

Chemical repellency in birds: relationship between chemical structure and avoidance response.

We examined how molecular structure of 24 anthranilate and benzoic acid derivatives correlated with drinking behavior in European starlings Sturnus vulgaris. The effectiveness of bird repellents was associated with basicity, the presence of an electron-donating group in resonance with an electron-withdrawing carboxylic group on a phenyl ring, and a heterocyclic ring in the same pi cloud plane as the phenyl ring. Of the benzoic acid derivatives tested in this study, methyl, ethyl, dimethyl, and linalyl anthranilate as well as anthranilic acid and 4-ketobenztriazine were repellent to birds. Water consumption was significantly reduced relative to control levels at concentrations as low as 0.05% (weight/volume) for the best repellents. Further statistical tests showed that reduction in consumption for the best repellents was absolute, not significantly different from zero consumption. Anthranilic acid isomers were moderately good repellents. The ability to generate a model predicting repellency allows for the efficient identification and development of ecologically sound, nonlethal, taxa-specific repellents to be used for the protection of wildlife in agricultural and industrial applications.

Animals↗