Category: 73590-85-9

On October 5, 2018, Nishiguchi, Shigenobu; Izumi, Takuhiro; Kouno, Takayoshi; Sukegawa, Junpei; Ilies, Laurean; Nakamura, Eiichi published an article.Related Products of 73590-85-9 The title of the article was Synthesis of Esomeprazole and Related Proton Pump Inhibitors through Iron-Catalyzed Enantioselective Sulfoxidation. And the article contained the following:

We report here an application of iron catalysis for the kilogram scale asym. synthesis of a proton pump inhibitor, esomeprazole, in 87% yield and 99.4% ee by catalytic sulfoxidation with hydrogen peroxide using an iron salt/chiral Schiff base in combination with a carboxylate salt. Under similar reaction conditions, other proton pump inhibitors such as (S)-lansoprazole, (S)-rabeprazole, and (S)-pantoprazole, were also synthesized in high yield and ee. A carboxylate additive was crucial for the success of this reaction, and we consider that it coordinates to the active iron species, and it also acts as a hydrogen-bond acceptor to coordinate to the substrate through the imidazole NH. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Related Products of 73590-85-9

The Article related to iron catalyzed enantioselective sulfoxidation esomeprazole synthesis, proton pump inhibitor synthesis iron catalyzed enantioselective sulfoxidation, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On November 30, 2011, Ogilvie, Brian W.; Yerino, Phyllis; Kazmi, Faraz; Buckley, David B.; Rostami-Hodjegan, Amin; Paris, Brandy L.; Toren, Paul; Parkinson, Andrew published an article.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: implications for coadministration with clopidogrel. And the article contained the following:

As a direct-acting inhibitor of CYP2C19 in vitro, lansoprazole is more potent than omeprazole and other proton pump inhibitors (PPIs), but lansoprazole does not cause clin. significant inhibition of CYP2C19 whereas omeprazole does. To investigate this apparent paradox, we evaluated omeprazole, esomeprazole, R-omeprazole, lansoprazole, and pantoprazole for their ability to function as direct-acting and metabolism-dependent inhibitors (MDIs) of CYP2C19 in pooled human liver microsomes (HLM) as well as in cryopreserved hepatocytes and recombinant CYP2C19. In HLM, all PPIs were found to be direct-acting inhibitors of CYP2C19 with IC50 values varying from 1.2 μM [lansoprazole; maximum plasma concentration (Cmax) = 2.2 μM] to 93 μM (pantoprazole; Cmax = 6.5 μM). In addition, we identified omeprazole, esomeprazole, R-omeprazole, and omeprazole sulfone as MDIs of CYP2C19 (they caused IC50 shifts after a 30-min preincubation with NADPH-fortified HLM of 4.2-, 10-, 2.5-, and 3.2-fold, resp.), whereas lansoprazole and pantoprazole were not MDIs (IC50 shifts < 1.5-fold). The metabolism-dependent inhibition of CYP2C19 by omeprazole and esomeprazole was not reversed by ultracentrifugation, suggesting that the inhibition was irreversible (or quasi-irreversible), whereas ultracentrifugation largely reversed such effects of R-omeprazole. Under various conditions, omeprazole inactivated CYP2C19 with KI (inhibitor concentration that supports half the maximal rate of inactivation) values of 1.7 to 9.1 μM and kinact (maximal rate of enzyme inactivation) values of 0.041 to 0.046 min-1. This study identified omeprazole, and esomeprazole, but not R-omeprazole, lansoprazole, or pantoprazole, as irreversible (or quasi-irreversible) MDIs of CYP2C19. These results have important implications for the mechanism of the clin. interaction reported between omeprazole and clopidogrel, as well as other CYP2C19 substrates. The experimental process involved the reaction of 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

The Article related to omeprazole lansoprazole pantoprazole esomeprazole proton pump inhibitor interaction cyp2c19, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 30, 2014, Zuo, Hui; Ma, Liangxiu published an article.Formula: C17H19N3O2S The title of the article was Study on green synthesis of omeprazole. And the article contained the following:

The aim is to study green synthesis of omeprazole. 4-Anisidine was treated via acetylation, nitration, hydrolysis, reduction and cyclization for synthesis of intermediate of 2-mercapto-5-methoxy-1H-benzimidazole. 2-Hydroxymethyl-3, 5-dimethyl-4-methoxy-pyridine was treated via sulfuryl chloride chlorination treatment to directly synthesize with benzimidazole to obtain intermediate of thioether without separation, and synthesis of omeprazole was achieved by catalytic oxidation The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Formula: C17H19N3O2S

The Article related to omeprazole green synthesis economic environment selective oxidation, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.Formula: C17H19N3O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Knych, H. K.; Stanley, S. D.; Arthur, R. M.; McKemie, D. S. published an article in 2017, the title of the article was Disposition of the anti-ulcer medications ranitidine, cimetidine, and omeprazole following administration of multiple doses to exercised Thoroughbred horses.HPLC of Formula: 73590-85-9 And the article contains the following content:

The use of anti-ulcer medications, such as cimetidine, ranitidine, and omeprazole, is common in performance horses. The use of these drugs is regulated in performance horses, and as such a withdrawal time is necessary prior to competition to avoid a medication violation. To the authors’ knowledge, there are no reports in the literature describing repeated oral administrations of these drugs in the horse to determine a regulatory threshold and related withdrawal time recommendations. Therefore, the objective of the current study was to describe the disposition and elimination pharmacokinetics of these anti-ulcer medications following oral administration to provide data upon which appropriate regulatory recommendations can be established. Nine exercised Thoroughbred horses were administered 20 mg/kg BID of cimetidine or 8 mg/kg BID of ranitidine, both for seven doses or 2.28 g of omeprazole SID for four doses. Blood samples were collected, serum drug concentrations were determined, and elimination pharmacokinetic parameters were calculated The serum elimination half-life was 7.05 ± 1.02, 7.43 ± 0.851 and 3.94 ± 1.04 h for cimetidine, ranitidine, and omeprazole, resp. Serum cimetidine and ranitidine concentrations were above the LOQ and omeprazole and omeprazole sulfide below the LOQ in all horses studied upon termination of sample collection. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).HPLC of Formula: 73590-85-9

The Article related to antiulcer ranitidine cimetidine omeprazole pharmacokinetics, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.HPLC of Formula: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 30, 2014, Yu, Yong; Li, Qin-geng published an article.Computed Properties of 73590-85-9 The title of the article was Synthesis of sodium esomeprazole. And the article contained the following:

Esomeprazole sodium was synthesized through asym. oxidation reaction, and the synthesis process route was optimized. The ufiprazole was prepared firstly, which was then oxidized to form esomeprazole. Finally, the esomeprazole sodium was prepared by reaction of esomeprazole with sodium hydroxide. The overall yield was 57.2%. The structures of target compounds were characterized by IR, 1H NMR and MS. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Computed Properties of 73590-85-9

The Article related to sodium esomeprazole chem synthesis, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.Computed Properties of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 15, 2012, Che, Guoyong; Xiang, Jing; Tian, Tian; Huang, Qingfei; Cun, Linfeng; Liao, Jian; Wang, Qiwei; Zhu, Jin; Deng, Jingen published an article.Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide catalyzed by a titanium complex with (S,S)-N,N’-dibenzyl tartramide ligand. And the article contained the following:

A chiral titanium complex, formed in situ from Ti(Oi-Pr)4, (S,S)-N,N’-dibenzyl tartramide, and water was found to serve as an efficient catalyst for the asym. oxidations of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide (CHP) in the absence of a base. Several proton pump inhibitors (PPIs), such as esomeprazole, lansoprazole, rabeprazole, and pantoprazole were obtained in high yield (up to 92%) and excellent enantiomeric excess (up to 96%). The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to asym oxidation benzimidazolyl pyridinylmethyl sulfide titanium tartramide catalyst, esomeprazole lansoprazole rabeprazole pantoprazole asym synthesis, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On August 31, 2022, Xu, Xinqi; Zhang, Yajiao; Wang, Shaoyu; Xu, Lian; Su, Bingmei; Wang, Lichao; Lin, Juan published an article.SDS of cas: 73590-85-9 The title of the article was Nonpolarity paving in substrate tunnel of a Limnobacter sp. Phenylacetone monooxygenase for efficient single whole-cell synthesis of esomeprazole. And the article contained the following:

Baeyer-Villiger monooxygenase (BVMO) mediated sulfoxidation is a sustainable approach for the synthesis of esomeprazole. In this work, a novel phenylacetone monooxygenase from Limnobacter sp. (LnPAMO) was found to have trace activity for synthesis of enantiopure esomeprazole. Through engineering in the substrate tunnel using a mutagenesis strategy called “nonpolarity paving” and some modifications in cofactor binding domains, a mutant harboring 15 mutations (LnPAMO Mu15) was obtained with 6.6 x 103-fold higher activity to convert omeprazole sulfide into esomeprazole. The activities of the mutant for synthesis of (S)-Me Ph sulfoxide and (S)-pantoprazole also increased much, indicating the versatility of the mutant for sulfoxide synthesis. Importantly, no over-oxidation byproduct omeprazole sulfone was detected in the sulfoxidation products by both mass spectrometry and HPLC anal. Then NADP-dependent Burkholderia stabili formate dehydrogenase was ligated behind Mu15 along with a ribosome binding site sequence in pET-28a for co-expression. By single whole-cell of recombinant Escherichia coli BL21 coexpressing Mu15 and formate dehydrogenase, omeprazole sulfide was efficiently converted into esomeprazole without production of sulfone (16 g/L substrate, enantiomeric excess > 99.9% (S) and > 99% conversion) and the space-time-yield reached 1.67 g product/L/h. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).SDS of cas: 73590-85-9

The Article related to esomeprazole limnobacter phenylacetone monooxygenase whole cell synthesis, esomeprazole, phenylacetone monooxygenase, single-cell sulfoxidation, substrate tunnel, Fermentation and Bioindustrial Chemistry: Fermentation Engineering and other aspects.SDS of cas: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On January 15, 2013, Si, Yuhui; Sun, Gangchun; Li, Zhicheng; Li, Yaping published an article.HPLC of Formula: 73590-85-9 The title of the article was Synthesis and resolution of omeprazole. And the article contained the following:

Omeprazole was synthesized and resolved by chiral resolution agent to obtain the S-isomer (Esomeprazole). The resolving conditions were as follows: S-(-)-1, 1′-Binaphthyl-2, 2′-diol, racemic omeprazole and alkali (molar ratio 1:1.6:1.8) reacted in ethanol and water (3.7:1 in v:v) at room temperature for 12 h. The magnesium salt of Esomeprazole was obtained in a high yield (89%) and excellent enantioselectivity (97.95% ee). The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).HPLC of Formula: 73590-85-9

The Article related to esomeprazole omeprazole synthesis chiral resolution, Pharmacology: Other (All Agents and Effects Not Otherwise Assignable) and other aspects.HPLC of Formula: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On August 31, 2015, Liu, Xiao-ping; Xu, Hui-lan; Sun, Rui; Li, Xue; Hu, Bao-hua; Hu, Chun published an article.Synthetic Route of 73590-85-9 The title of the article was Synthesis and characterization of two impurities in esomeprazole, an antiulcerative drug. And the article contained the following:

Impurity control is a key factor for drug quality. Study for impurities is helpful to optimize the production process and improve the quality of drugs. Synthesis and characterization of two of impurities in esomeprazole, which used for treatment of acid-related diseases was described in this paper. The two impurities are known as 2-[(3,5-dimethyl-4-methoxy-2-pyridinyl)methylsulfinyl]-1H-benzimidazole (impurity 1) and (R)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole (esomeprazole impurity F), whose structures are characterized with MS, IR, 1H-NMR and elemental analyses, and the purities of the two impurities are above 99% by HPLC anal. The two target compounds can be used as the reference substance of the impurities of esomeprazole. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Synthetic Route of 73590-85-9

The Article related to antiulcerative drug esomeprazole impurity acid disease, Pharmacology: Other (All Agents and Effects Not Otherwise Assignable) and other aspects.Synthetic Route of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On July 15, 2022, Zhu, Jun; Geng, Qiang; Liu, Yuan-Yang; Pan, Jiang; Yu, Hui Lei; Xu, Jian-He published an article.SDS of cas: 73590-85-9 The title of the article was Co-Cross-Linked Aggregates of Baeyer-Villiger Monooxygenases and Formate Dehydrogenase for Repeated Use in Asymmetric Biooxidation. And the article contained the following:

Baeyer-Villiger monooxygenases (BVMOs) are versatile biocatalysts, but their applications are hindered by their poor stability and cofactor dependence. In this study, cross-linked enzyme aggregate (CLEA) technol. was adopted to coimmobilize BVMO and its accessory cofactor-regeneration enzyme. Combi-CLEAs of a pyrmetazole monooxygenase from Acinetobacter calcoaceticus (AcPSMO) and a formate dehydrogenase from Burkholderia stabili (BstFDH) were prepared for the synthesis of (S)-omeprazole. After optimization, AcPSMO and BstFDH were coprecipitated with an activity ratio of 1:6 using ammonium sulfate and then cross-linked with glutaraldehyde (0.12% w/v). The activity recoveries of AcPSMO and BstFDH in the prepared combi-CLEAs were 43% and 38%, resp. Compared with the free enzymes AcPSMO and BstFDH, the thermostabilities of AcPSMO and BstFDH in combi-CLEAs were improved by 2.5- and 1.6-fold, resp. Both enzymes were more stable against alk. buffer after being immobilized. The combi-CLEAs could be reused for seven cycles in the biooxidative synthesis of (S)-omeprazole without significant activity loss, indicating the excellent operational stability and reusability in repeated reactions for the enzymic synthesis of (S)-omeprazole. Another two combi-CLEAs prepared under the same conditions, TmCHMO-BstFDH and RpBVMO-BstFDH, can be reused for at least 15 consecutive batches for the cyclohexanone mono-oxygenation reaction, which indicates the promising potential for coimmobilization of BVMOs and FDH with CLEA methodol. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).SDS of cas: 73590-85-9

The Article related to baeyer villiger monooxygenase formate dehydrogenase crosslinked aggregate asym biooxidation, Fermentation and Bioindustrial Chemistry: Methods (Including Analysis) and other aspects.SDS of cas: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem