A clinical comparison of Panadeine Co., soluble codeine co., soluble aspirin in the relief of pain.
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Acetaminophen↗
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Results for “Solubility”
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Studies on the soluble ribonucleic acid of Escherichia coli. The nucleotide sequences adjacent to the 5'-phosphomonoester terminal of the soluble ribonucleic acid.
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Chromatography↗
[On the use of the absorption-elution method in identification of water-soluble ABH group-specific substances. II. Separation of an alcohol-soluble fraction and of an alcohol-precipitable fraction of ABH substances from saliva].
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ABO Blood-Group System↗
[Effect of excitation of some physio-chemical properties (solubility, buffer capacity and ionizing capacity) of cytoplasmic soluble proteins of the brain].
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Animals↗
Immunogenic properties of soluble antigens or whole cells of Brucella abortus strain 45/20 associated with immunoadjuvants. I. Soluble antigens.
A purified protein derivative-live preparation of Brucella abortus strain 45/20 was tested for immunogenic properties either alone, after lipid conjugation, or in association with defined adjuvants. The adjuvants were trehalose dimycolate (cord factor), isolated from wax D of mycobacteria and murmyl dipeptide (N-acetyl-muramyl-L-alamyl-D-isoglutamine), a synthetic glycopeptide analog of peptidoglycan subunits found in many bacterial cell walls and wax D of mycobacteria. Guinea pigs were intradermally inoculated with a single injection of the vaccine preparations eight weeks before intramuscular challenge with B. abortus, strain 2308. None of the purified protein derivative-like preparations were as effective in the prevention of splenic infections with B. abortus as were killed whole cells of strain 45/20 in Freund's complete adjuvant. Whole cells in Freund's complete adjuvant were able to reduce mean colony counts by 97% (P = 0.02), while purified protein derivative-like vaccines were able to reduce mean colony counts by only 32 to 61% as compared to control animals. Results suggest that purified protein derivative-like preparations have limited immunogenic properties under present test conditions.
Acetylmuramyl-Alanyl-Isoglutamine↗
Soluble E-selectin and soluble intercellar adhesion molecule-1 in coronary artery disease.
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Coronary Disease↗
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs.
PURPOSE: The purpose of this study was to assess if the definition of high solubility as proposed in the FDA Guidance on Biopharmaceutical Classification System (BCS) is too strict for highly permeable acidic drugs. METHODS: The solubility and permeability values of 20 (18 acidic and 2 non-acidic) nonsteroidal anti-inflammatory drugs (NSAID) were determined. The NSAIDs were grouped into three different sets having acetic acid, propionic acid, or other acidic moieties such as fenamate, oxicam, and salicylate. Two nonacidic NSAIDs (celecoxib and rofecoxib) were also included for comparison purposes. Equilibrium solubility values were determined at pH 1.2, 5.0, 7.4, and in biorelevant media simulating fed intestinal fluid at pH 5.0. For a select number of acids, we also measured solubility values in media simulating gastric and fasted intestinal fluids. Permeability classification was established relative to that of reference drugs in the Caco-2 cell permeability model. Permeability coefficients for all drugs were measured at concentrations corresponding to the lowest and highest marketed dose strengths dissolved in 250 ml volume, and their potential interaction with cellular efflux pumps was investigated. RESULTS: All NSAIDs with different acidic functional groups were classified as highly permeable based on their Caco-2 cell permeability. Only ketorolac appeared to have a potential for interaction with cellular efflux pumps. Solubility classification was based on comparison of equilibrium solubility at pH 1.2, 5.0. and 7.4 relative to marketed dose strengths in 250 ml. The pKa values for the acidic NSAIDs studied were between 3.5 and 5.1. and, as expected, their solubility increased dramatically at pH 7.4 compared to pH 1.2. Only three NSAIDs, ketorolac, ketoprofen. and acetyl salicylic acid, meet the current criteria for high solubility over the entire pH range. However, with the exception of ibuprofen, oxaprozin, and mefenamic acid, the remaining compounds can be classified as Class I drugs (high solubility-high permeability) relative to solubility at pH 7.4. The use of bio-relevant media simulating gastric and intestinal milieu for solubility measurements or increasing the dose volume to 500 ml did not provide for a better boundary for solubility classification. CONCLUSIONS: Based on the current definition of solubility, 15 of the 18 acidic NSAIDs in this study will be classified as Class II compounds as the solubility criteria applies to the entire pH range of 1.2 to 7.4, although the low solubility criteria does not hold true over the entire pH range. Whence, of the 18 acidic drugs, 15 can be classified as Class I based on the pH 7.4 solubility alone. This finding is intriguing because these drugs exhibit Class I behavior as their absorption does not seem to be dissolution or solubility limited. It could then be argued that for acidic drugs, the boundaries for solubility are too restrictive. Solubility at pH > 5 (pH in duodenum) may be more appropriate because most compounds are mainly absorbed in the intestinal region. Consideration for an intermediate solubility classification for highly permeable ionizable compounds that reflects physiological conditions seems warranted.
Acids↗
Solubility and related physicochemical properties of narcotic analgesics.
The physicochemical properties of select opioid and anilinopiperidine narcotic analgesics were investigated. The solubilities of the narcotics in hexane and water and, for morphine, in other organic solvents were determined. Regular solution theory seems to be applicable to the solubility behavior of morphine in solvents that lack strong dipoles and hydrogen bonds. A best-fit solubility parameter of 13.2 (cal/cm3)1/2 for morphine was determined from its solubilities in London solvents and its ideal solubility. Calculation of morphine's solubility parameter from its hexane solubility alone and its melting properties gave a corresponding delta 2 value. These measured solubility parameters were appreciably larger than the solubility parameter estimated from molar attraction constants. Solubility parameters of hydromorphone, codeine, fentanyl, and sufentanil were also calculated from respective hexane solubilities, melting points, and heats of fusion and were 11.7, 10.9, 9.8, and 9.7 (cal/cm3)1/2. For these compounds, experimental solubility parameters agreed with solubility parameters estimated from molar attraction constants. Because meperidine, fentanyl, and sufentanil exhibit low levels of intracrystalline cohesion, as reflected in low melting points and relatively modest heats of fusion, theoretically projected ideal solubilities and actual solubilities in organic solvents measured for them were considerably higher than determined for morphine and its analogues. Consistent with the solubilities, the octanol-water partition coefficients of the two 4-anilinopiperidine analogues and of meperidine were several orders of magnitude larger than those of the opioids, evidencing the fact that meperidine, fentanyl, and sufentanil are substantially more lipophilic than the opioids.
Analgesics, Opioid↗
Modulation of soluble guanylate cyclase activity by phosphorylation.
The levels of the cGMP in smooth muscle of the gut reflect continued synthesis by soluble guanylate cyclase (GC) and breakdown by phosphodiesterase 5 (PDE5). Soluble GC is a haem-containing, heterodimeric protein consisting alpha- and beta-subunits: each subunit has N-terminal regulatory domain and a C-terminal catalytic domain. The haem moiety acts as an intracellular receptor for nitric oxide (NO) and determines the ability of NO to activate the enzyme and generate cGMP. In the present study the mechanism by which protein kinases regulate soluble GC in gastric smooth muscle was examined. Sodium nitroprusside (SNP) acting as a NO donor stimulated soluble GC activity and increased cGMP levels. SNP induced soluble GC phosphorylation in a concentration-dependent fashion. SNP-induced soluble GC phosphorylation was abolished by the selective cGMP-dependent protein kinase (PKG) inhibitors, Rp-cGMPS and KT-5823. In contrast, SNP-stimulated soluble GC activity and cGMP levels were significantly enhanced by Rp-cGMPS and KT-5823. Phosphorylation and inhibition of soluble GC were PKG specific, as selective activator of cAMP-dependent protein kinase, Sp-5, 6-DCl-cBiMPS had no effect on SNP-induced soluble GC phosphorylation and activity. The ability of PKG to stimulate soluble GC phosphorylation was demonstrated in vitro by back phosphorylation technique. Addition of purified phosphatase 1 inhibited soluble GC phosphorylation in vitro, and inhibition was reversed by a high concentration (10 microM) of okadaic acid. In gastric smooth muscle cells, inhibition of phosphatase activity by okadaic acid increased soluble GC phosphorylation in a concentration-dependent fashion. The increase in soluble GC phosphorylation inhibited SNP-stimulated soluble GC activity and cGMP formation. The results implied the feedback inhibition of soluble GC activity by PKG-dependent phosphorylation impeded further formation of cGMP.
Carbazoles↗
Extended Hildebrand Solubility Approach: methylxanthines in mixed solvents.
The solubility profiles of theobromine, theophylline, and caffeine at 25 degrees were examined in binary solvent systems including dioxane-formamide, water-polyethylene glycol 400, and glycerin-propylene glycol. Theobromine solubility was studied in dioxane-water mixtures, a solvent system that was investigated earlier for the solubility of theophylline and caffeine. Solubilities were calculated in these polar systems by a regression method, based on an extension of the Hildebrand-Scatchard equation of regular solution theory. A linear relationship between the mixed solvent solubility parameter, and dielectric constant, epsilon, was introduced earlier and was confirmed in the present study. In addition, it was observed that a regression of log (activity coefficient) on epsilon in a second or higher degree polynomial provides reasonable solubility values for the methylxanthines in mixed solvents. A direct regression of molal or mole fraction (but not molar) solubility against delta 1, epsilon, or against volume percent of one or the other solvent in a binary solvent mixture provided a suitable measure of solubility for these crystalline drugs in mixed polar solvents. The drug's solubility parameter as determined from peak solubility in mixed polar solvents varied somewhat, depending on the specific solvent system employed. It is suggested that a drug may exhibit one (or more) solubility parameters in nonpolar solutions and multiple solubility parameters in polar systems. The extended solubility approach serves for the back-calculation of solubilities in mixed solvent systems, even though the solubility parameter of the solute may vary from one solvent system to the next.
Caffeine↗
Extended Hildebrand solubility approach: sulfonamides in binary and ternary solvents.
The extended Hildebrand solubility approach is used to estimate the solubility of sulfonamides in binary and ternary solvent systems. The solubility of sulfisomidine in the binary solvent, dioxane-water, shows a bell-shaped profile with a solubility maximum well above the ideal solubility of the drug. This is attributed to solvation of the drug with the dioxane-water solvent, and indicates that the solute-solvent interaction energy (W) is larger than the geometric mean (delta 1 delta 2) of regular solution theory. The solubilities of sulfadiazine, sulfisomidine, sulfathiazole, and sulfamethoxazole were determined in mixtures of dimethylacetamide, glycerol, and water, and the solubility profiles were well reproduced by use of the extended Hildebrand solubility approach. Since the solubility parameter (delta 1 = 11) of the solvent (dimethylacetamide) was approximately equal to the solubility parameters of the sulfonamides, and because of the powerful solvating power of dimethylacetamide, the solubility profiles did not exhibit peaks as observed for sulfisomidine in dioxane-water. When sulfisomidine was dissolved in a ternary mixture, i.e., butyl acetate (delta 1 = 8.5), dimethylacetamide (delta 1 congruent to 11), and methanol (delta 1 = 14.5), a spike was produced in the solubility profile at the solubility parameter of dimethylacetamide. This sharply peaked profile suggests that the two branches be treated as separate solubility curves, which are then independently well reproduced by the extended Hildebrand solubility approach. None of the four sulfonamides yielded log-linear relationships in the ternary mixtures.
Acetamides↗
Development of water-soluble prodrugs of the HIV-1 protease inhibitor KNI-727: importance of the conversion time for higher gastrointestinal absorption of prodrugs based on spontaneous chemical cleavage.
We designed and synthesized a series of water-soluble prodrugs of the HIV-1 protease inhibitor KNI-727 (1), which is a sparingly water-soluble drug with a water solubility of 5.5 microg/mL. These prodrugs, which contain a water-soluble auxiliary with two tandem-linked units, i.e., a self-cleavable spacer and a solubilizing moiety with an ionized amino function, exhibited a marked increase in water solubility (>10(4)-fold) compared with the parent drug 1. The mechanism of conversion to the parent drug 1 is not enzymatic but through a chemical cleavage at the spacer via an intramolecular cyclization-elimination reaction through an imide formation under physiological conditions. To diversify the conversion time for the parent drug regeneration, chemical modification of the auxiliary was carried out focusing on the introduction of cyclic tertiary amines, which can modify the basicity and/or conformational flexibility of the terminal amino function at the solubilizing moiety, and the change in bond length, which can attenuate the five-membered ring intermediate formation in the cleavage. These newly synthesized water-soluble prodrugs exhibited a practical water solubility with values greater than 50 mg/mL and enabled the constant regeneration of the parent drug 1 with diversified conversion times ranging from 4 min to 34 h as t(1/2) values under physiological conditions. All the water-soluble prodrugs tested regenerated the parent drug 1 in vivo as well as in vitro. A clear increase in the gastrointestinal absorption was observed in prodrugs 8, 12, and 13 with bioavailability (BA) values of 23%, 26%, and 29%, respectively. These BA values were 1.5-1.9-fold higher than that in the administration of the parent drug 1 alone. Other prodrugs showed only a similar or decreased BA compared to the parent drug 1. From these results, we found that not only a high water solubility but also an appropriate conversion time of the prodrug with a relatively narrow limit of around 35 min via intraduodenal administration was necessary for significant improvement of the gastrointestinal absorption in water-soluble prodrugs based on the spontaneous chemical cleavage. This is the first successful water-soluble prodrug that suggests an increased BA value greater than the parent drug in HIV-1 protease inhibitors and is the first study to show the importance of optimal conversion time in water-soluble prodrugs. Consequently, a water-soluble strategy that can control the conversion time would be extensively applicable to improve the gastrointestinal absorption of sparingly water-soluble drugs. The present information is an intriguing discovery and is one of the key factors that will contribute to the future design of practical water-soluble prodrugs.
Animals↗
Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins.
Aqueous solubility is an important parameter for the development of liquid formulations and in the determination of bioavailability of oral dosage forms. Ibuprofen (IB), a nonsteroidal anti-inflammatory drug, is a chiral molecule and is currently used clinically as a racemate (racIB). However, the S form of ibuprofen or S(+)-ibuprofen (SIB) is the biologically active isomer and is primarily responsible for the antiinflammatory activity. Phase solubility studies were carried out to compare the saturation solubilities of racIB and SIB in the presence of common pharmaceutical solvents such as glycerol, sorbitol solution, propylene glycol (PG), and polyethylene glycol (PEG 300) over the range of 20% to 80% v/v in aqueous based systems. The solubilities of the two compounds were also compared in the presence of cyclodextrins such as beta cyclodextrin (CD), hydroxypropyl beta cyclodextrin (HPCD), and beta cyclodextrin sulfobutyl ether sodium salt (CDSB) over the range of 5% to 25% w/v. Solubility determinations were carried at 25 degrees C and 37 degrees C. Cosolvents exponentially increased the solubility of both SIB and racIB, especially in the presence of PG and PEG 300. Glycerol was not very effective in increasing the aqueous solubilities of both compounds, whereas sorbitol solution had a minimal effect on their solubility. PG and PEG 300 increased the solubility of SIB by 400-fold and 1500-fold, respectively, whereas the rise in solubility for racIB was 193-fold and 700-fold, respectively, at 25 degrees C for the highest concentration of the cosolvents used (80% v/v). Of the two compounds studied, higher equilibrium solubilities were observed for SIB as compared with racIB. The derivatized cyclodextrins increased the aqueous solubility of racIB and SIB in a concentration-dependent manner giving AL type of phase diagrams. The phase solubility diagrams indicated the formation of soluble inclusion complexes between the drugs and HPCD and CDSB, which was of 1:1 stoichiometry. The addition of underivatized CD reduced the solubility of racIB and SIB via the formation of an insoluble complex. The S form formed more stable complexes with HPCD and CDSB as compared with raclB. The solubilization process is discussed in terms of solvent polarity and differential solid-state structure of raclB and SIB. The thermodynamic parameters for the solubilization process are presented.
Cyclodextrins↗
Solubility of hydrophobic organic pollutants in binary and multicomponent aqueous solvents.
The present paper deals with the application of fluctuation theory of solutions to the solubility of poorly soluble substances of environmental significance in aqueous mixed solvents. The fluctuation theory of ternary solutions was first used to derive an expression for the activity coefficient of a solute at infinite dilution in a binary mixed solvent. This equation contains the activity coefficients of the constituents of the solute-free mixed solvent and the molar volume of the solute-free mixed solvent. Further, the derived expression for the activity coefficient of a solute at infinite dilution was used to generate a number of expressions for the solubility of solids in aqueous mixed solvents. Several expressions for the activity coefficients of the components were considered: first, the mixed solvent was considered an ideal mixture; second, the activity coefficients of the constituents of the binary solvent were expressed using the two-suffix Margules equations; third, the activity coefficients of the constituents of the binary solvent were expressed using the Wilson equations. The obtained expressions were applied to 25 experimental data sets pertaining to the solubilities of hydrophobic organic pollutants (HOP) in aqueous mixed solvents. It was found that the suggested equations can be used for an accurate and reliable correlation of the solubilities in aqueous mixed binary solvents. The best results were obtained by combining our expression for the activity coefficient of a solute at infinite dilution in a mixed solvent with the Wilson equations for the activity coefficients of the constituents of a solute-free mixed solvent. The derived equations can also be used for predicting the solubilities of poorly soluble environmentally important compounds in aqueous mixed solvents using for the Wilson parameters those obtained from vapor-liquid equilibrium data. A similar methodology was applied to the solubility of poorly soluble substances of environmental significance in multicomponent (ternary and higher) aqueous mixed solvents. The expression for the activity coefficient of a solute in an ideal multicomponent mixed solvent was used to derive an equation for the solubility of a poorly soluble solute in an ideal multicomponent mixed solvent in terms of its solubilities in two subsystems of the multicomponent solvent and their molar volumes. Ultimately the solubility could be expressed in terms of those in binary or even in the individual constituents of the solvent and their molar volumes. The computational method was applied to predict the solubilities of naphthalene and anthracene in ternary, quaternary and quinary aqueous mixed solvents. The results were compared with experiment and good agreement was obtained.
Models, Theoretical↗
Soluble HLA-G circulates in maternal blood during pregnancy.
OBJECTIVE: Soluble isoforms of the HLA class Ib gene HLA-G have been identified at the maternal-fetal interface. Because soluble forms of other HLA class I antigens modulate T-cell reactivity and induce cellactivated apoptosis, our goal was to determine whether soluble HLA-G circulates in maternal or fetal blood and to identify the specific isoform. STUDY DESIGN: Capture enzyme-linked immunosorbent assays with mouse monoclonal antibodies directed toward an epitope present on all isoforms of soluble HLA-G were constructed to identify soluble HLA-G in 44 serum samples from nonpregnant control subjects, 129 serum samples from pregnant women, and 10 samples of term cord blood. Distinguishing between soluble HLA-G1, which is composed of heavy chains complexed with light chains (beta(2)-microglobulin), and soluble HLA-G2, which consists only of heavy chains, was achieved by substituting a monoclonal antibody that requires beta(2)-microglobulin for binding (W6/32) in the capture phase of the enzyme-linked immunosorbent assay. RESULTS: Capture enzyme-linked immunosorbent assays with mouse anti-soluble HLA-G showed that soluble HLA-G was present at all stages of gestation and that levels of soluble HLA-G were statistically significantly higher in serum samples from pregnant women than in serum samples from nonpregnant women. In contrast, W6/32 failed to detect soluble HLA-G in serum samples from pregnant women. Cord serum samples did not contain detectable soluble HLA-G. CONCLUSION: Collectively, the data indicate that pregnancy is characterized by the presence of soluble HLA-G circulating in maternal blood and strongly suggest that the major isoform is soluble HLA-G2.
Animals↗
Characterization of a soluble KGF receptor cDNA from human corneal and breast epithelial cells.
PURPOSE: Keratinocyte growth factor (KGF) is a member of the fibroblast growth factor (FGF) family FGF-7. It exhibits potent mitogenic activity for epithelial cells, including corneal and mammary epithelial cells. A messenger RNA has been reported that is generated by alternative splicing of bek that putatively codes only for the extracellular ligand-binding domain of KGF receptor (soluble KGF receptor). In the present study, the expression of the mRNA coding for this alternative bek transcript was examined and the corresponding protein characterized. METHODS: Alternative messenger RNA transcripts were detected in various cell lines or tissues using reverse transcription-polymerase chain reaction (RT-PCR) and RNase protection assay. NIH/3T3 fibroblast cells and 293 kidney embryonic epithelial cells were stably transfected with soluble KGF receptor cDNA and transmembrane KGF receptor cDNA. Soluble KGF receptor protein was produced using a baculovirus-insect expression system. Soluble KGF receptor protein was detected using western and dot blot analyses. Binding assays and cross-linking labeling were used to determine the affinity and specificity of soluble KGF receptor. A mitogenic assay was performed to examine the function of the soluble KGF receptor. RESULTS: The soluble KGF receptor mRNA was primarily expressed in epithelial cells, including cells from the cornea and breast. Cross-linking labeling and affinity-binding assays with 125I-KGF showed that the soluble KGF receptor bound KGF (FGF-7) but not FGF-1 or FGF-2. Soluble KGF receptor was detected in the culture medium of cells stably transfected with soluble KGF receptor cDNA but not with transmembrane KGF receptor cDNA, suggesting that the soluble receptor was generated by mRNA splicing and probably not by proteolysis or posttranslational processing. Soluble KGF receptor inhibited KGF binding to transmembrane KGF receptor and DNA synthesis in BALB/MK epidermal keratinocytes in response to KGF, suggesting that soluble KGF receptor expression could provide a mechanism for the cell to downregulate responses to KGF. CONCLUSIONS: A truncated soluble KGF receptor expressed in corneal and other epithelial cells probably functions to downregulate the response of the cell to KGF.
3T3 Cells↗
Extended Hildebrand approach: solubility of caffeine in dioxane-water mixtures.
The solubility of caffeine in various dioxane-water mixtures was analyzed in terms of solute-solvent interactions using a modified version of the Hildebrand treatment for regular solutions. The solubility equation employs a term (W) to replace the geometric mean (c1c2)1/2, where c1 and c2 are the cohesive energy densities for the solvent and solute, respectively. The new equation provides an accurate prediction of solubility once the interaction energy, W, is obtained. In this case, the energy term is regressed against a polynomial in delta 1 of the binary mixture. A quartic expression of W in terms of the solvent solubility parameter was found for predicting the solubility of caffeine in dioxane-water mixtures. The expression yields an error in mole fraction solubility of less than 3%, a value approximating that of the experimentally determined solubility. The one exception to a good fit is near the maximum solubility, where a depression or valley occurs between the two peaks in solubility data; at this point, the theoretical equation predicts the solubility within approximately 9%. The new model also may be used to estimate the solubility of drug molecules employing the volume fraction of water in the solvent mixture instead of the composite solubility parameter, delta 1. The method has potential usefulness in preformulation and formulation studies during which solubility determination is important for drug design.
Caffeine↗
Expanded solubility parameter approach. II: p-Hydroxybenzoic acid and methyl p-hydroxybenzoate in individual solvents.
The recently introduced four-parameter extended Hansen approach was used to study the solubility of p-hydroxybenzoic acid and methyl p-hydroxybenzoate in 32 and 35 individual solvents, respectively. The results are compared with those for benzoic acid in 40 solvents. Seventeen of the thirty-two or 53% of the calculated solubilities of p-hydroxybenzoic acid were within the established solubility criterion (i.e., less than 30% error from the experimental value). Twenty-two of thirty-six or 61% of the calculated solubility values for methyl p-hydroxybenzoate met the solubility criterion. Experimental excess free energies of solution for p-hydroxybenzoic acid and methyl p-hydroxybenzoate were plotted against theoretical values using the expanded four-parameter solubility regression equations. From such results, adjustments may be made in the partial solubility parameters to bring the calculated solubilities in line with experimental results. Multiple regression analyses were used to estimate the total solubility parameter and the four partial solubility parameters of the two benzoic acid derivatives. Satisfactory results were obtained for methyl p-hydroxybenzoate, but poor agreement was found for p-hydroxybenzoic acid for the total parameter when compared with the Fedors group contribution method. Both the multiple regression and group contribution methods may yield inaccurate solubility parameters for relatively polar solid solutes. Factor analysis was used to test the adequacy of three- and four-parameter approaches in the evaluation of drug solubility. A principal factor method without iteration and orthogonal factor rotation were used to compare the two expanded solubility parameter approaches.(ABSTRACT TRUNCATED AT 250 WORDS)
Chemical Phenomena↗