Omeprazole

H+,K+-ATPase inhibitor CAS# 73590-58-6

Omeprazole

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Chemical structure

Omeprazole

3D structure

Chemical Properties of Omeprazole

Cas No. 73590-58-6 SDF Download SDF
PubChem ID 4594 Appearance Powder
Formula C17H19N3O3S M.Wt 345.42
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (289.50 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
SMILES CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
Standard InChIKey SUBDBMMJDZJVOS-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Omeprazole

DescriptionH+,K+-ATPase inhibitor (IC50 = 5.8 μM) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC50 = 0.16 μM for histamine-induced acid formation) and reduces gastric lesion formation induced by a variety of ulcerative stimuli. Antibacteral against Helicobacter pylori in vitro. Also inhibits CYP2C19, CYP2C9 and CYP3A (Ki values are 3.1, 40.1 and 84.4 μM respectively) and blocks swelling-dependent chloride channels (ICIswell).

Omeprazole Dilution Calculator

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Omeprazole Molarity Calculator

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Preparing Stock Solutions of Omeprazole

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.895 mL 14.4751 mL 28.9503 mL 57.9005 mL 72.3757 mL
5 mM 0.579 mL 2.895 mL 5.7901 mL 11.5801 mL 14.4751 mL
10 mM 0.2895 mL 1.4475 mL 2.895 mL 5.7901 mL 7.2376 mL
50 mM 0.0579 mL 0.2895 mL 0.579 mL 1.158 mL 1.4475 mL
100 mM 0.029 mL 0.1448 mL 0.2895 mL 0.579 mL 0.7238 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Omeprazole

H+,K+-ATPase inhibitor (IC50 = 5.8 μM) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC50 = 0.16 μM for histamine-induced acid formation) and reduces gastric lesion f

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References on Omeprazole

Photochemical transformation and wastewater fate and occurrence of omeprazole: HRMS for elucidation of transformation products and target and suspect screening analysis in wastewaters.[Pubmed:28284641]

Sci Total Environ. 2017 Jul 15;590-591:592-601.

Omeprazole is one of the world-wide most frequently prescribed and administered pharmaceuticals in humans for the relief of gastro-intestinal disorders. Despite its high worldwide consumption, Omeprazole is rarely detected in urban wastewaters and environmental waters. On the other hand, its human urinary metabolites and transformation products formed through abiotic processes in the environment have been recently documented. Despite these available data, however, there is still a lack of information on the extent of environmental fate and occurrence, on elimination mechanisms and efficiencies in waste water treatment plants. In this study, the relevance of photodegradation processes on the environmental persistence of Omeprazole under simulated and solar irradiation was investigated. Photodegradation experiments were performed in distilled water, lake, river and seawater, and revealed that the different matrix in natural waters significantly affect the photolytic behavior of the investigated compound. Overall, the results highlight that photodegradation process by solar irradiation significantly contributes to Omeprazole degradation and elimination from the aquatic environment. TPs formed through the process were identified and elucidated by using liquid chromatography high resolution mass spectrometry. In total seven TPs were identified, among of which four were also detected as hydrolysis TPs. The Microtox bioassay showed that solar photolysis is efficient to detoxify Omeprazole and its TPs in aqueous solutions. Finally, a systematic investigation was conducted in order to provide information on removal efficiency and occurrence of Omeprazole and its metabolites/TPs in 8 WWTPs in North West Greece by performing target and suspect screening analysis. The findings revealed the presence of both parent compound and metabolites/TPs in wastewaters. Given, however, the scarce detection of Omeprazole at fairly low concentration levels, from analytical and environmental point of view, further attention should be given to metabolites/TPs instead of the parent compound.

The effect of omeprazole treatment on the gut microflora and neutrophil function.[Pubmed:28258834]

Clin Res Hepatol Gastroenterol. 2017 Oct;41(5):575-584.

BACKGROUND AND AIM: Proton pump inhibitors (PPIs) may increase the risk of Clostridium difficile infections. There are interactions between gut microbiota and innate immune cells including neutrophils. We evaluated the effect of treatment with Omeprazole on the gut microflora and neutrophil function. METHODS: In 50 patients, we evaluated the effect of 4-week Omeprazole treatment (n=25 with 20mg per day and n=25 with 20mg twice daily) on intragastric pH, results of stool culture and lactulose hydrogen breath test (LHBT) and neutrophil function. RESULTS: The treatment caused significant increase of the mean intragastric pH, especially in the group with 20mg Omeprazole twice daily (from 2.05+/-0.59 to 5.06+/-1.6, P<0.001). In LHBT, the increase of hydrogen concentration was observed in higher percentage of patients with 20mg of Omeprazole twice daily, compared to patients with the lower dose (42.1% vs 29.4%; ns). Four weeks of Omeprazole treatment have caused considerable changes in stool culture results. Patients treated with higher dose of Omeprazole have had some tendency to decrease diversity of colonic microflora in comparison with patients treated with the lower dose of Omeprazole. Treatment with Omeprazole did not result in C. difficile positive stool culture and had no significant effect on neutrophil function. CONCLUSIONS: Omeprazole treatment have caused considerable changes in stool culture results. Patients treated with the higher dose had some tendency to decreased diversity of colonic microflora and towards changes in fermenting bacteria of the gut. The potential effect of Omeprazole on gut microflora does not depend on neutrophil function deterioration.

Affinity capillary electrophoresis and fluorescence spectroscopy for studying enantioselective interactions between omeprazole enantiomer and human serum albumin.[Pubmed:28229517]

Electrophoresis. 2017 May;38(9-10):1366-1373.

Baseline separation of Omeprazole (OME) enantiomers was achieved by affinity capillary electrophoresis (ACE), using human serum albumin (HSA) as the chiral selector. The influence of several experimental variables such as HSA concentration, the type and content of organic modifiers, applied voltage and running buffer concentration on the separation was evaluated. The binding of esOmeprazole (S-Omeprazole, S-OME) and its R-enantiomer (R-Omeprazole, R-OME) to HSA under simulated physiological conditions was studied by ACE and fluorescence spectroscopy which was considered as a reference method. ACE studies demonstrated that the binding constants of the two enantiomers and HSA were 3.18 x 10(3) M(-1) and 5.36 x 10(3) M(-1) , respectively. The binding properties including the fluorescence quenching mechanisms, binding constants, binding sites and the number of binding sites were obtained by fluorescence spectroscopy. Though the ACE method could not get enough data when compared with the fluorescence spectrum method, the separation and binding studies of chiral drugs could be achieved simultaneously via this method. This study is of great significance for the investigation and clinical application of chiral drugs.

Application of nickel zinc ferrite/graphene nanocomposite as a modifier for fabrication of a sensitive electrochemical sensor for determination of omeprazole in real samples.[Pubmed:28182955]

J Colloid Interface Sci. 2017 Jun 1;495:1-8.

In the present study, a simple and highly sensitive sensor for the determination of Omeprazole based on nickel-zinc ferrite/graphene modified glassy carbon electrode is reported. The morphology and electro analytical performance of the fabricated sensor were characterized with X-ray diffraction spectrometry, Fourier transform infrared spectrometry, scanning electron microscopy, electrochemical impedance spectroscopy, cyclic voltammetry, differential pulse voltammetry and operation of the sensor. Results were compared with those achieved at the graphene modified glassy carbon electrode and bare glassy carbon electrode. Under the optimized experimental conditions, linear response was over the range of 0.03-100.0micromolL(-1). The lower detection limit was found to be 0.015micromolL(-1). The effect of different interferences on the anodic current response of OMZ was investigated. By measuring the concentrations of Omeprazole in plasma and pharmaceutical samples, the practical application of the modified electrode was evaluated. This revealed that the nickel-zinc ferrite/graphene modified glassy carbon electrode shows excellent analytical performance for the determination of Omeprazole with a very low detection limit, high sensitivity, and very good accuracy.

The gastric H,K-ATPase blocker lansoprazole is an inhibitor of chloride channels.[Pubmed:10711360]

Br J Pharmacol. 2000 Feb;129(3):598-604.

1. It was postulated that swelling dependent chloride channels are involved in the proton secretion of parietal cells. Since Omeprazole, lansoprazole and its acid activated sulphenamide form AG2000 are structurally related to phenol derivatives known to block swelling dependent chloride channels, we set out to test, whether these substances--which are known to block the H,K-ATPase--could also lead to an inhibition of swelling-dependent chloride channels. Swelling-dependent chloride channels--characterized in many different cell types--show highly conserved biophysical and pharmacological features, therefore we investigated the effect of Omeprazole, lansoprazole and its acid activated sulphenamide form AG2000 on swelling-dependent chloride channels elicited in fibroblasts, after the reduction of the extracellular osmolarity. 2. Omeprazole, lansoprazole and its acid activated sulphenamide form AG2000 are able to block swelling-dependent chloride channels (IClswell). 3. Lansoprazole and its protonated metabolite AG2000 act on at least two different sites of the IClswell protein: on an extracellular site which seems to be in a functional proximity to the nucleotide binding site, and on an intracellular site which allows the formation of disulfide-bridges. 4. The inhibition of the proton pump and the simultaneous blocking of chloride channels by Omeprazole, lansoprazole and its acid activated sulphenamide form AG2000, as described here could be an effective mode to restrict proton secretion in parietal cells.

Proton pump inhibitors. Pharmacology and rationale for use in gastrointestinal disorders.[Pubmed:9777309]

Drugs. 1998 Sep;56(3):307-35.

Proton pump inhibitors (PPIs) are drugs which irreversibly inhibit proton pump (H+/K+ ATPase) function and are the most potent gastric acid-suppressing agents in clinical use. There is now a substantial body of evidence showing improved efficacy of PPIs over the histamine H2 receptor antagonists and other drugs in acid-related disorders. Omeprazole 20 mg/day, lansoprazole 30 mg/day, pantoprazole 40 mg/day or rabeprazole 20 mg/day for 2 to 4 weeks are more effective than standard doses of H2-receptor antagonists in healing duodenal and gastric ulcers. Patients with gastric ulcers should receive standard doses of PPIs as for duodenal ulcers but for a longer time period (4 to 8 weeks). There is no conclusive evidence to support the use of a particular PPI over another for either duodenal or gastric ulcer healing. For Helicobacter pylori-positive duodenal ulceration, a combination of a PPI and 2 antibacterials will eradicate H. pylori in over 90% of cases and significantly reduce ulcer recurrence. Patients with H. pylori-positive gastric ulcers should be managed similarly. PPIs also have efficacy advantages over ranitidine and misoprostol and are better tolerated than misoprostol in patients taking nonsteroidal anti-inflammatory drugs (NSAIDs). In endoscopically proven gastro-oesophageal reflux disease, standard daily doses of the PPIs are more effective than H2-receptor antagonists for healing, and patients should receive a 4 to 8 week course of treatment. For severe reflux, with ulceration and/or stricture formation, a higher dose regimen (Omeprazole 40 mg, lansoprazole 60 mg, pantoprazole 80 mg or rabeprazole 40 mg daily) appears to yield better healing rates. There is little evidence that PPIs lead to resolution of Barrett's oesophagus or a reduction of subsequent adenocarcinoma development, but PPIs are indicated in healing of any associated ulceration. In Zollinger-Ellison syndrome, PPIs have become the treatment of choice for the management of gastric acid hypersecretion.

Antisecretory and antiulcer activities of a novel proton pump inhibitor AG-1749 in dogs and rats.[Pubmed:2537418]

J Pharmacol Exp Ther. 1989 Feb;248(2):806-15.

The antisecretory and antiulcer activities of 2[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl] sulfinyl]-1H-benzimidazole (AG-1749) were investigated in dogs and rats. AG-1749 inhibited both the (H+ + K+)-adenosine triphosphatase activity in canine gastric microsomes and dibutyryl cyclic AMP-stimulated acid formation in isolated canine parietal cells and suppressed the acid secretion stimulated by histamine, pentagastrin, bethanechol or a peptone meal in Heidenhain pouch dogs; the ID50 values were between 0.2 and 0.7 mg/kg p.o. AG-1749 inhibited both the histamine-stimulated and the basal acid secretion in pylorusligated rats and prevented water immersion stress or aspirin-induced gastric lesions and mepirizole or cysteamine-induced duodenal ulcers in rats; the ID50 values were between 0.3 to 3.6 mg/kg p.o. or i.d. Furthermore, AG-1749 prevented gastric lesions induced by absolute ethanol or acidified aspirin, and accelerated the healing of acetic acid-induced gastric or duodenal ulcers in rats. The inhibitory potency of AG-1749 in dogs was much the same as that of Omeprazole and about half that of ranitidine. However, it was about 2 to 10 times more potent than Omeprazole and 4 to 34 times more potent than ranitidine in rats. These results suggest that AG-1749 exerts prominent antiulcer activities mainly by suppressing acid secretion via an inhibition of a proton pump in gastric parietal cells and partly by protecting the gastrointestinal mucosa against various ulcerative stimuli.

Description

Omeprazole (H 16868), a proton pump inhibitor (PPI), is available for treatment of acid-related gastrointestinal disorders. Omeprazole shows competitive inhibition of CYP2C19 activity with a Ki of 2 to 6 μM. Omeprazole also inhibits growth of Gram-positive and Gram-negative bacteria.

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