The origin of a common compound about 73590-85-9

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Quality Control of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Development of a validated RP-HPLC method for separation and determination of process-related impurities of omeprazole in bulk drugs. Author is Iuga, Cristina; Bojita, Marius; Leucuta, Sorin E..

A gradient reversed phase liquid chromatog. (RP-LC) method was developed and subsequently validated for the determination of omeprazole and its process-related impurities (noted as: impurity A, B, C, D, G, H). Separation was achieved with a Zorbax Extend C18 column and acetonitrile: water: triethylaminel percent (pH adjusted to 9.5) as eluent, at a flow rate of 0.8 mL/min. UV detection was performed at 280 nm. The described method was linear over a range of 40.6-203 μg/mL for omeprazole, 0.9556-14.334 μg/mL for impurity A, 1.1568-17.352 μg/mL for impurity B, 1.0772-16.158 μg/mL for impurity C, 1.289-19.344 μg/mL for impurity D, and 0.7968-11.952 μg/mL for impurity H. The accuracy of the method was demonstrated at 5 concentration levels in the range of 60-140% of the specification limit and the recovery of impurities was found to be in the range of 90-109%. The method is simple, rapid, selective, accurate, and useful for indicating the stability of omeprazole from dosage forms. The method can be useful in the quality control of bulk manufacturing and pharmaceutical formulations.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Simultaneous high-performance liquid chromatographic analysis of omeprazole and its sulfone and sulfide metabolites in human plasma and urine, the main research direction is omeprazole metabolite determination blood urine; liquid chromatog omeprazole metabolite.Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole.

Omeprazole  [73590-58-6], a substituted benzimidazole which suppresses gastric acid secretion, and its sulfone [88546-55-8] and sulfide [73590-85-9] metabolites were simultaneously measured in human plasma and urine using a selective, reversed-phase, high-performance liquid chromatog. method with a sensitivity of 5 ng/mL for omeprazole, 30 ng/mL for omeprazole sulfone, and 50 ng/mL for omeprazole sulfide. The coefficients of variation for within-day assays were 4.4, 7.5, and 17.5%, resp. In a pilot pharmacokinetic study, 40 mg of omeprazole (encapsulated enteric-coated granules) were administered to 2 healthy volunteers. Peak plasma concentrations for omeprazole of 240 and 520 ng/mL, and for omeprazole sulfone of 320 and 400 ng/mL, were reached between 3 and 4 post-dose. Omeprazole concentrations fell rapidly with apparent half-lives of about 40 min, and concentrations of both omeprazole and the sulfone metabolite were below the minimal detectable level by 6-8 h. Omeprazole sulfide could not be detected in this study.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Evidence for acid-induced transformation of omeprazole into an active inhibitor of proton-potassium ATPase within the parietal cell, published in 1984, which mentions a compound: 73590-85-9, Name is 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, Molecular C17H19N3O2S, Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole.

The chem. reactions of omeprazole (I) [73590-58-6], leading to inhibition of gastric acid secretion, were investigated. In acid buffer solutions, omeprazole was found to be labile, whereas at physiol. pH it was stable (t1/2 > 17 h at pH 7.4). The stability of omeprazole was also studied in isolated, acid producing, gastric glands under conditions where acid formation was either stimulated or inhibited. The rate of transformation of omeprazole was high (t1/2 ≈ 3 min) under stimulation. Inhibition of acid formation in the gland greatly retarded the decomposition of omeprazole (t1/2 ≈ 73 min). The time-course for inhibition of acid formation by omeprazole was parallel to that for decomposition The major product formed from omeprazole was the reduced form, H 168/22 (II) [73590-85-9]. The inhibitory action of omeprazole was shown to depend on acid-induced transformation, since no inhibition was obtained when omeprazole was incubated under neutral conditions, both in the isolated gastric mucosal- and the (H+ + K+)-ATPase  [9000-83-3] preparations Despite the fact that H 168/22 was the major product formed in the glandular preparation, it was found to be virtually inactive in both the glandular and (H+ and K+)-ATPase preparations Therefore, a model is proposed in which the inhibition of acid formation by omeprazole is mediated by a compound formed during the reduction of omeprazole to H 168/22 within the acid compartments of the parietal cell. Furthermore, mercaptans, such as β-mercaptoethanol, were found to prevent as well as reverse inhibition by omeprazole in both the glandular- and (H+ + K+)-ATPase preparations This indicates that -SH groups are most likely involved in the chem. reactions leading to inhibition of acid secretion.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Boix, C.; Ibanez, M.; Zamora, T.; Sancho, J. V.; Niessen, W. M. A.; Hernandez, F. researched the compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole( cas:73590-85-9 ).Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole.They published the article 《Identification of new omeprazole metabolites in wastewaters and surface waters》 about this compound( cas:73590-85-9 ) in Science of the Total Environment. Keywords: omeprazole metabolite wastewater surface water urine analysis sample pollution; Metabolites; Omeprazole; Time-of-flight mass spectrometry; Triple quadrupole mass spectrometry; Urine; Water samples. We’ll tell you more about this compound (cas:73590-85-9).

Omeprazole is 1 of the world-wide most consumed pharmaceuticals for treatment of gastric diseases. As opposed to other frequently used pharmaceuticals, omeprazole is scarcely detected in urban wastewaters and environmental waters. This was corroborated in a previous research, where parent omeprazole was not detected while 4 transformation products (TPs), mainly resulting from hydrolysis, were found in effluent wastewaters and surface waters. However, the low abundance of omeprazole TPs in the H2O samples together with the fact that omeprazole suffers an extensive metabolism, with a wide range of excretion rates (between 0.01 and 30)̂, suggests that human urinary metabolites should be studied in the H2O environment. The results obtained in excretion tests after administration of a 40 mg omeprazole dose in 3 healthy volunteers are reported. Anal. by liquid chromatog. coupled to hybrid quadrupole time-of-flight mass spectrometry (LC-QTOF MS) reported low concentrations of omeprazole in urine. Up to 20-four omeprazole metabolites (OMs) were detected and tentatively elucidated. The most relevant OM was an omeprazole isomer, which obviously presented the same exact mass (m/z 346.1225), but also shared a major common fragment at m/z 198.0589. Subsequent analyses of surface H2O and effluent wastewater samples by both LC-QTOF MS and LC-MS/MS with triple quadrupole revealed that this metabolite (named as OM10) was the compound most frequently detected in H2O samples, followed by OM14a and OM14b. Up to the knowledge, OM10 had not been used before as urinary biomarker of omeprazole in waters. On the contrary, parent omeprazole was never detected in any of the H2O samples. After this research, it seems clear that monitoring the presence of omeprazole in the aquatic environment should be focused on the OMs suggested in this article instead of the parent compound

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Formula: C17H19N3O2S. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Improved procedure for quantitation of omeprazole and metabolites using reversed-phase high-performance liquid chromatography. Author is Amantea, Michael A.; Narang, Prem K..

An HPLC procedure for the determination of omeprazole and its sulfone and sulfide metabolites in human plasma was developed by using a C8 reversed-phase column with a mobile phase of MeOH-MeCN-0.025M phosphate buffer (40:8:52) adjusted to pH 7.4 with 85% H3PO4 and detection at 302 nm. The level of detection was 5, 10, and 7.5 ng/mL for omeprazole, its sulfone, and the sulfide, resp. and the intraday variability ranged 2.6-10.3 and 2.0-3.5% at 10 and 125 ng/mL, resp. The recoveries were 96, 42, and 96% for omeprazole, the sulfone, and the sulfide, resp.

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Song, Weiguo; Dong, Liangjun; Zhou, Yuhan; Fu, Yongqiang; Xu, Wenfang published an article about the compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole( cas:73590-85-9,SMILESS:CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC ).Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:73590-85-9) through the article.

An efficient synthesis of esomeprazole I via catalytic asym. oxidation of 1H-benzimidazolyl pyridinylmethyl sulfide by a titanium complex with a hexa-aza-triphenolic macrocycle ligand is described. Esomeprazole was prepared with 99.6% ee, which meets the high requirement of the European Pharmacopeia on enantiomeric purity.

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Recommanded Product: 73590-85-9. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about A blockbuster synthesis for undergraduates. Author is Parsons, Andrew F..

A context-based practical designed to give students the opportunity to improve their team working, communication and time-management skills was developed. By investigating the synthesis of the major antiulcer drug, esomeprazole, undergraduates are given an insight into the challenges of modern process chem., from optimization of the lead compound to its full-scale manufacture Students work as a team to prepare pyrmetazole from pyrmethyl alc. and then investigate the reaction conditions required to optimize the asym. oxidation of the sulfide group in pyrmetazole to form esomeprazole. Students do a series of small-scale oxidation reactions, using reagents and reaction conditions of their choice, to investigate how the conditions affect the efficiency of the oxidation They are required to plan their experiments to maximize the number of results they achieve over the eight-day period of the project and then provide a summary of their results and describe aspects of scaling-up their optimized reaction in individual reports, which are assessed. Their results are reviewed and compared with the current industrial process.

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Recommanded Product: 73590-85-9. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Effect of hypoxia on oxidative and reductive pathways of omeprazole metabolism by the isolated perfused rat liver. Author is Webster, Lorraine K.; Jones, D. Brian; Mihaly, George W.; Morgan, Denis J.; Smallwood, Richard A..

The effect of hypoxia on the elimination of H168-68 (omeprazole)(I) [73590-58-6] a potent inhibitor of gastric acid secretion, was studied in the isolated perfused rat liver. During normal oxygenation, a 10 mg bolus dose was eliminated rapidly (half-life (T1/2)-β = 8.0 min), while under hypoxic conditions T1/2β was increased to 81.6 min. Upon reoxygenation, T1/2β returned to 9.6 min. During hypoxia, perfusate concentrations of an oxidative metabolite (I-sulfone [88546-55-8]) were reduced by 68%, while those of the reductively-generated I-sulfide [73590-85-9] increased 4-fold. With reoxygenation, both formation and elimination of the sulfone were increased, whereas, which had accumulated during the hypoxic period, was eliminated rapidly. These findings were duplicated in steady-state experiments, in which omeprazole clearance during hypoxia fell by at least 70%, and sulfide concentrations in perfusate rose from undetectable levels to 200 ng/mL (at least a 10-fold increase). Sulfone concentrations did not change with hypoxia, consistent with a reduction in both its formation and elimination rates. Thus, the hepatic elimination of omeprazole is severely retarded by hypoxia, but this effect is promptly reversed by reoxygenation. The increased formation of the reductive metabolite during hypoxia is not of sufficient magnitude to sustain the normal hepatic elimination of omeprazole.

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Quality Control of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Mechanism of the asymmetric sulfoxidation in the esomeprazole process: effects of the imidazole backbone for the enantioselection.

The asym. sulfoxidation reaction of imidazole-based prochiral sulfides was studied to explore the mechanistic details of the highly efficient esomeprazole process, which is one of the few industrial scale catalytic asym. procedures. The synthetic studies revealed that the smallest subunit governing the selectivity in the esomeprazole process is an imidazole ring. Thus, by using the esomeprazole procedure Me imidazole sulfide could be oxidized as efficiently as its several functionalized derivatives, including pyrmetazol. However, alkylation of the imidazole nitrogen led to a major drop of the enantioselectivity. Our atm. pressure chem. ionization-mass spectrometry (APCI/MS) studies indicate that addition of small amounts of water to the reaction mixture facilitates the formation of mononuclear titanium species, which are the active catalytic intermediates of the selective oxidation reaction. One of the most important features of the esomeprazole procedure is that amine additives increase the enantioselectivity of the oxidation process. The NMR studies of the presumed reaction intermediates show that under catalytic conditions the amines are able to coordinate to titanium and dissociate the coordinated imidazole substrate. The d. functional theory (DFT) modeling studies provided new insights in the mechanism of the asym. induction. It was found that the oxidation requires a lower activation energy if the imidazole sulfide precursor does not coordinate to titanium. Two possible reaction paths were explored for this out of sphere oxidation mechanism. The most important interaction governing the enantioselection is hydrogen bonding between the N-H of the imidazole ring and the chiral tartrate ligand on titanium. Furthermore, the oxidation reaction imposes an important structural constraint to the TS structure involving a linear arrangement of the peroxide oxygens and the sulfur atom. This constraint and the N coordination of imidazole leads to a very strained structure for the inner sphere mechanism of the oxidation, which leads to a much higher activation barrier than the corresponding out of sphere process, and therefore it is unlikely.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Evidence for acid-induced transformation of omeprazole into an active inhibitor of proton-potassium ATPase within the parietal cell, published in 1984, which mentions a compound: 73590-85-9, Name is 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, Molecular C17H19N3O2S, Recommanded Product: 73590-85-9.

The chem. reactions of omeprazole (I) [73590-58-6], leading to inhibition of gastric acid secretion, were investigated. In acid buffer solutions, omeprazole was found to be labile, whereas at physiol. pH it was stable (t1/2 > 17 h at pH 7.4). The stability of omeprazole was also studied in isolated, acid producing, gastric glands under conditions where acid formation was either stimulated or inhibited. The rate of transformation of omeprazole was high (t1/2 ≈ 3 min) under stimulation. Inhibition of acid formation in the gland greatly retarded the decomposition of omeprazole (t1/2 ≈ 73 min). The time-course for inhibition of acid formation by omeprazole was parallel to that for decomposition The major product formed from omeprazole was the reduced form, H 168/22 (II) [73590-85-9]. The inhibitory action of omeprazole was shown to depend on acid-induced transformation, since no inhibition was obtained when omeprazole was incubated under neutral conditions, both in the isolated gastric mucosal- and the (H+ + K+)-ATPase  [9000-83-3] preparations Despite the fact that H 168/22 was the major product formed in the glandular preparation, it was found to be virtually inactive in both the glandular and (H+ and K+)-ATPase preparations Therefore, a model is proposed in which the inhibition of acid formation by omeprazole is mediated by a compound formed during the reduction of omeprazole to H 168/22 within the acid compartments of the parietal cell. Furthermore, mercaptans, such as β-mercaptoethanol, were found to prevent as well as reverse inhibition by omeprazole in both the glandular- and (H+ + K+)-ATPase preparations This indicates that -SH groups are most likely involved in the chem. reactions leading to inhibition of acid secretion.

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