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PubMedDate not supplied

Simultaneous spectrophotometric determination of paracetamol and salicylamide in human serum and pharmaceutical formulations by a differential kinetic method.

A rapid, simple, and sensitive differential kinetic method is presented for the determinations of acetaminophen (also known as paracetamol) and salicylamide. The method is based on their oxidation reaction by Fe3+ ion in the presence of 1, 10-phenanthroline as indicator. The reactions can be monitored spectrophotometrically by measuring the increase in the absorbance of the solution at 510 nm. Two times were selected one in which only paracetamol is oxidized by Fe3+ ion and the other in which both drugs are oxidized by Fe3+ ion. The data were evaluated by the proportional equations method. The method allowed the simultaneous determination of paracetamol and salicylamide at concentrations between 0.5-20 and 1-40 microg/mL with relative standard deviations of 3.47 and 2.58%, respectively. The method was applied to the simultaneous determination of paracetamol and salicylamide in human serum and pharmaceutical formulations.

Acetaminophen↗
PubMed1990

Syntheses of [123I]-, [125I]- and unlabelled (S)-3-iodo-5,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]salicylamide (NCQ 298), selective ligands for the study of dopamine D-2 receptors.

The salicylamide NCQ 298, (S)-3-iodo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5,6-dimethoxysalicylami de (4), binds with a high affinity and selectivity to central dopamine D-2 receptors. In the present paper the synthesis of NCQ 298 and the efficient labelling both with 123I and 125I are described. The unlabelled NCQ 298 was synthesized by iodination of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,5,6-trimethoxybenzamide followed by demethylation with boron tribromide, which produced 4 and the regioisomer 5 in a ratio of 82:18. The two isomeric salicylamides were separated by radial chromatography and tested for their abilities to inhibit the binding of [3H]raclopride to rat striatal membranes in vitro in relation to some representative salicylamides. The 5,6-dimethoxysalicylamide 4 (NCQ 298) was found to be considerably more active than the corresponding 6-methoxysalicylamide 10 (FLA 961 or IBZM). The radioligands [123I]NCQ 298 and [125I]NCQ 298 were prepared in a carrier-free form from the corresponding desiodo compound by the chloramine-T protocol and isolated by semipreparative HPLC. The total radiochemical yields of [123I]NCQ 298 and [125I]NCQ 298 (based on [123I]- and [125I]iodide and decay-corrected) were 88% and 93%, respectively, with a radiochemical purity of greater than 99%. [125I]NCQ 298 will be studied to evaluate its potential as a radioligand in studies requiring a high specific activity, selectivity and high potency to label dopamine D-2 receptors. [123I]NCQ 298 has potential as a radioligand for the in vivo examination of central dopamine D-2 receptors in human brain by Single Photon Emission Computed Tomography (SPECT).

Animals↗
PubMed1982

An effect of sulfur nutrition on the metabolism of salicylamide.

The effect of supplementing diets containing 15% casein with inorganic sulfate and/or the sulfur-containing amino acids on the metabolism of salicylamide was determined. The glucuronide-salicylamide:sulfate-salicylamide (GS:SS) ratio in the urine of rats fed the diets containing 15% of casein without inorganic sulfate or sulfur containing amino acid supplementation approached unity. Addition of either 0.02% of inorganic sulfate or 0.625% of methionine reduced this ratio to approximately 0.3%. Addition of 0.325% of methionine or sufficient cysteine to be equimolar with 0.625% methionine did not lower the GS:SS ratio significantly. Therefore, it appears that not only the level but the source of sulfur may be important in the detoxication of drugs.

Animals↗
PubMed1980

[Multiple-dose pharmacokinetics of paracetamol and salicylamide in man after combined rectal application (author's transl)].

The pharmacokinetic behaviour of paracetamol (300 mg) and salicylamide (200 mg) in the course of combined repetitive (three times tau = 4 h) administration of suppositories was investigated in 10 healthy, male volunteers. The estimation of the pharmacokinetic constants was performed by a simultaneous curve fitting from all single values with a direct search procedure, based on an open two-compartment model and the multiple-dose equation. Both drugs showed a pharmacokinetic behaviour which was conformable to the literature data for single dose and mono substance applications. The dynamics of the absorption kinetics was decreased, as is generally seen after the application of suppositories. In spite of this both substances reached a steady state after the 3rd application. A calculation of collapse coefficients showed for paracetamol as well as for salicylamide a pharmacokinetic distribution behaviour deviating from an open one-compartment model. Due to the good conformity of the parameters, which causes the synchronism of the time-concentration curves after multiple dose application, paracetamol and salicylamide are suited combination partners as seen from a pharmacokinetic point of view.

Acetaminophen↗
PubMed1975

Effect of carbonated beverages and of an antiemetic containing carbohydrate and phosphoric acid on riboflavin bioavailability and salicylamide biotransformation in humans.

Two carbohydrate-phosphoric acid solutions, one a widely used beverage (Solution C) and the other a pharmaceutical product used as an antiemetic (Solution E), administered together with riboflavin-5'-phosphate or salicylamide to healthy human adults, significantly increased the bioavailability of riboflavin and appreciably altered the metabolic fate of salicylamide (increased conversion to the sulfate and decreased formation of the glucuronide). A beverage containing phosphoric acid but no carbohydrates (Solution T) also increased the bioavailability of riboflavin but not as much as Solution C. These effects are attributed to a decrease of the gastric emptying rate caused by carbohydrates and phosphoric acid, consistent with the empirical use of Solution C syrup and Solution E as antinauseants and antiemetics. The results demonstrate also that the choice of beverage to be taken with medication can affect the bioavailability and/or metabolic fate of medicinals with saturable absorption and/or biotransformation characteristics.

Adult↗
PubMed1977

Effect of coadministered salicylamide on terbutaline metabolism in rats.

Concomitant oral administration of salicylamide (200 mg/kg) and 3H-terbutaline (1 mg/kg) to rats with ligated bile ducts decreased absorption of terbutaline from the gut from 73 to 56% as measured by urinary excretion of radioactivity in 48 hr. No increase in the fraction of terbutaline excreted unchanged was observed, suggesting that salicylamide does not substantially inhibit the conjugation of terbutaline with glucuronic acid. An increase in the fraction of terbutaline excreted unchanged observed in normal animals may result from enhanced excretion of terbutaline glucuronide into bile rather than from inhibition of conjugation.

Animals↗
PubMed1977

The dissolution mechanism in a system undergoing complexation: salicylamide in caffeine solution.

The dissolution rate of compressed salicylamide discs has been measured in water and in caffeine solutions of increasing concentration at 15, 25, 37 and 45 degrees in an apparatus rotating at 48 rev min-1 or more. Dissolution rate profiles showed breaks indicative of a shift in the mechanism of dissolution from interfacial towards transport control. The shifts occurred at higher caffeine concentrations on increasing the agitation rate or temperature. The dependencies of dissolution rates on agitation rates typified the intermediate type of dissolution and Arrhenius plots indicated that interfacial and transport processes participated in salicylamide dissolution.

Caffeine↗
PubMed1982

Release kinetics of sparingly soluble drugs from ethyl cellulose-walled microcapsules: salicylamide microcapsules.

Release rates of salicylamide from single-core ethyl cellulose (EC) coated microcapsules were measured as a function of wall thickness and core particle size. Whereas up to ca 50% release zero order kinetics were observed, the overall reaction fitted the first order and Higuchi matrix treatment. These were distinguished by the differential rate treatment, which showed that the overall release in fact followed the first order pattern. For investigating whether the process was membrane-controlled, the experimental rate constants were transformed into effective permeability constants (P0 and P1) with the aid of the microcapsule dimensional parameters needed in the relevant equations and compared with the salicylamide permeability constant for planar ethyl cellulose membranes (P), measured experimentally. P0 and P1 values obtained for a given microcapsule preparation were not identical: P0 was of the same order as P, P1 being much lower. While membrane-controlled release is evident, it is apparently accompanied by a first order concentration gradient change inside the microcapsule.

Capsules↗
PubMed1987

Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist.

The structure of the potent dopamine-D2 antagonist, raclopride, (S)-3,5-dichloro-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamid e (+)-tartrate, has been determined by X-ray crystallography. The benzamide moiety of raclopride is planar in accordance with other salicylamides (FLA 797 and eticlopride). The planar conformation is stabilized by two intramolecular hydrogen bonds, i.e. one between the amide hydrogen and the methoxy group and one between the phenol hydrogen and the carbonyl group. The side-chain of raclopride has an extended conformation in contrast to the solid state conformations of FLA 797 and eticlopride. The side-chain conformations were studied by rigid rotations followed by MM2PI relaxations of the eight local minima found. Small energy differences (less than 4.0 kcal mol-1) exist between the various extended and folded conformations. Based on modelling studies with piquindone as template, it is suggested that the salicylamides with N-ethyl-2-pyrrolidinylmethyl side-chains interact with the dopamine-D2 receptor in a folded or a half-folded conformation.

Crystallization↗
PubMed1978

Hypnotic effectiveness of sodium salicylamide with short-term use: sleep laboratory studies.

Sodium salicylamide in doses of 650 and 1,300 mg was evaluated in two separate sleep laboratory drug evaluation studies of insomniac patients. Each study utilized a standard protocol of 10 consecutive laboratory nights consisting of four placebo nights for adaptation and baseline, three drug nights for short-term drug administration and three placebo nights for evaluating withdrawal. Neither dose had a clear-cut hypnotic effect in inducing or maintaining sleep. Sleep stages were not effected by drug administration or drug withdrawal. Both the objective findings and subjective estimates suggest that the 1,300-mg dose may have a slight sedative effect. However, when salicylamide is used as an ingredient in over-the-counter preparations, the usual dose is only 200-400 mg.

Adult↗
PubMed1979

[Salicylamide-- a potential pain-remedy alternative in the analgesic asthma syndrome].

Central pathogenetic mechanism of the analgesics-asthma-syndrome is very probably an analgesics-conditioned inhibition of the prostaglandin-biosynthesis (cyclooxygenase). Salicylamide, an analgesic without effect on the prostaglandin synthesis was in the oral exposition test of 18 patients with proved analgesics-asthma-syndrome in the dosage of 500 mg subjectively and objectively tolerated without reaction. Body-plethysmographically in consistent thoracic gas volume a slight decrease of the airways resistance could be registered. At the model of the isolated trachea of guinea-pigs salicylamide, in contrast to indomethacin and phenazone (prostaglandin-synthesis inhibitory substances) did not lead to an increase of the acetylcholine-induced spasm. Salcylamide can, after a tolerability test, be recommended as alternative analgesic in the analgesics-asthma-syndrome in a dosage of 500 mg.

Analgesics↗
PubMed2004

Lipophilicity study of salicylamide.

Molecular lipophilicity was studied using salicylamide as a model drug. Log P value for the target compound was experimentally determined by the shake-flask method and calculated using nine different computer programs based on atom/fragment contributions, structural parameters, atom-type electrotopological-state indices and neural network modeling, or topological structure descriptors. Our analysis demonstrates good agreement between the experimentally observed log P value of salicylamide and the value calculated by the CSLogP program, based on topological structure descriptors and electrotopological indices.

Computer Simulation↗
PubMed1989

Synthesis and evaluation of the analgesic and antiinflammatory activities of N-substituted salicylamides.

Some N-heterocyclic salicylamide derivatives were prepared by fusion of phenyl salicylate and heterocyclic amines, whereas other ones were synthesized by ring closure using N-salicyloyl-N'-anthranylhydrazine as starting material. All the compounds were tested for their analgesic and antiinflammatory activities, as well as for their acute toxicity and ulcerogenic effects, in order to ascertain if the N-substitution would offer any advantages. Some derivatives were more effective than salicylamide and ulcerogenic activity was variably lowered.

Animals↗
PubMed1986

Solid state conformations and antidopaminergic effects of remoxipride hydrochloride and a closely related salicylamide, FLA 797, in relation to dopamine receptor models.

The X-ray structures of two new 2,6-disubstituted benzamides, i.e., remoxipride hydrochloride monohydrate [-)-(S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenza mide hydrochloride monohydrate) and FLA 797 [-)-(S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamide ), have been determined as well as the distribution coefficients. The difference in dopamine receptor blocking activity is discussed in terms of lipophilicity and solid state conformations of the two benzamides. The major difference between the solid state conformations lies in the orientation of the carboxamide moiety. In remoxipride the carbonyl group is oriented almost perpendicularly to the benzene ring, thus preventing the formation of a hydrogen-bonded pseudo-ring between the amide hydrogen and the methoxy group found in other types of o-methoxybenzamides. In FLA 797, however, this pseudo-ring is present in the planar conformation of the salicylamide moiety. This conformation is further stabilized by a hydrogen bond between the phenol group and the carbonyl oxygen. The side chain in remoxipride adopts an extended conformation in contrast to FLA 797, where the side chain has a folded conformation. The crystal structures are related to current topographic dopamine receptor models developed from more rigid antidopaminergic compounds. Based on these comparisons, it is suggested that benzamides having an N-ethyl-2-pyrrolidinylmethyl side chain interact with the receptor in the folded conformation. The binding affinity is thought to be further increased by the planar conformation of the salicylamide moiety present in FLA 797, which permits an efficient pi-pi stacking interaction.

Benzamides↗
PubMed1985

Availability studies on acetylsalicylic acid, salicylamide and phenacetin at different pH values.

The optimum partitioning rate of acetylsalicylic acid has been attained at pH = 4 and minimum partitioning rate was found to be at pH = 8. The maximum partitioning rate of salicylamide was observed at pH = 5 and the smallest one was found at pH = 6 or 8. At pH = 3 a maximum amount of phenacetin was found in the aqueous phase, while at pH = 6 a maximum amount was found in the octanolic layer. The maximum partitioning rate was found at pH = 6 and lowest one was observed at pH = 3. The gastrointestinal absorption of acetylsalicylic acid, salicylamide and phenacetin was significantly increased, as reflected by the urinary excretion data in presence of solid buffer components at pH values of 4,5 and 6 respectively.

Adult↗
PubMedDate not supplied

Excretion of D-glucaric acid and metabolism of salicylamide in man: the effect of phenobarbital-produced enzymatic induction.

In 16 young healthy subjects the composition of salicylamide metabolites and the rate of their excretion depended on the loading dose. After 5 days of treatment with phenobarbital, the excretion of glucaric acid (GLA) and the rate of excretion and degree of glucuronization of salicylamide metabolites increased over 2-fold. The rate of excretion and degree of glucuronization were correlated with the amount of excreted GLA. The value of assay of GLA for the assessment of induction of hepatocytic microsomal enzymes is discussed.

Adult↗
PubMed2006

Voltammetric analysis of europium at screen-printed electrodes modified with salicylamide self-assembled on mesoporous silica.

Mercury-free sensors for europium (Eu(3+)) assay based on the chemical modification of screen-printed carbon electrodes (SPCEs) with self-assembled salicylamide on mesoporous silica (Sal-SAMMS) have been developed. The preconcentration of Eu(3+) at SAMMS-based sensors utilizes the binding affinity of the salicylamide and Eu(3+), accomplished at open circuit potential without electrolyte and solution de-gassing. Optimal Eu detection was obtained after 3-5 min preconcentration in Eu solution (pH 2-6), electrolysis at -0.9 V for 60 s in a new medium (0.1-0.2 M NH(4)Cl, pH 3.5), followed by a square-wave voltammetric detection of Eu in the same electrolyte. Attributed to the strong covalent bonding of the functional groups on mesoporous silica and silane cross-linking, the SAMMS-modified SPCEs with a built-in 3-electrode system can be re-used for tens of measurements with minimal degradation, enabling the establishment of the calibration curve and lowering the costs. A linear calibration curve was found in the range of 75 to at least 500 ppb Eu(3+) after 5 min preconcentration. The experimental detection limit was 10 ppb after 10 min preconcentration, which can be improved with increased preconcentration time. Reproducibility (% RSD) of 100 ppb Eu(2+) was 10% for a single sensor and 10% for 5 sensors, which can be improved through the precision of sensor manufacturing, in which SAMMS modification can be made in-situ.

Journal Article↗
PubMed1994

Salicylamides containing amino acid or pyran moieties with molluscicidal activity.

Salicylamide amino acid conjugates were prepared utilizing 5-formyl-, 5-dicyanoethenyl-, and 5-nitroethenylsalicylic acid. 5-Substituted salicylanilides were treated with glycine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-glycino)salicylanilides. The reactions of anilines with pyrans containing the salicylyl moiety yielded the corresponding salicylanilides. The obtained compounds were tested for molluscicidal activity.

Amino Acids↗