Omeprazole
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04530 |
| CAS | 73590-58-6 |
| Molecular Weight | 345.42 |
| Molecular Formula | C17H19N3O3S |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04530 | 25 g | $197 | In stock |
Online Inquiry
Add to cartDescription
Omeprazole is a proton pump inhibitor used in the treatment of dyspepsia. It binds to the proton pump hydrogen-potassium adenosine triphosphatase (H+/K+ ATPase) and inhibits its activity and the parietal cell secretion of H+ ions into the gastric lumen.
Specification
| Related CAS | 95510-70-6 (sodium) |
| Synonyms | OMEP; OMP; OMZ; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; Antra; Losec; Gastrogard; Gastroloc; Mepral; Mopral; Omepral; Prilosec; Zoltum; (±)-Omeprazole |
| Storage | Store at -20°C |
| IUPAC Name | 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole |
| Canonical SMILES | CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC |
| 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) |
| InChI Key | SUBDBMMJDZJVOS-UHFFFAOYSA-N |
Properties
| Appearance | White to Pale Beige Solid |
| Application | Anti-ulcer agents; enzyme inhibitors |
| Boiling Point | 600.0±60.0°C (Predicted) |
| Melting Point | >114°C (dec.) |
| Density | 1.332 g/cm3 |
| Solubility | Soluble in Ethanol (5 mg/ml at 25°C), DMSO, DMF |
| LogP | 2.23 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Omeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, omeprazole blocks the final step in acid production, thus reducing gastric acidity. |
Reference Reading
1. Pharmacokinetic drug-drug interaction assessment of LCZ696 (an angiotensin receptor neprilysin inhibitor) with omeprazole, metformin or levonorgestrel-ethinyl estradiol in healthy subjects.
Gan L1, Jiang X2, Mendonza A1, Swan T1, Reynolds C2, Nguyen J2, Pal P3, Neelakantham S3, Dahlke M4, Langenickel T4, Rajman I4, Akahori M5, Zhou W2, Rebello S2, Sunkara G2. Clin Pharmacol Drug Dev. 2016 Jan;5(1):27-39. doi: 10.1002/cpdd.181. Epub 2015 Nov 4.
LCZ696 is a novel angiotensin receptor neprilysin inhibitor in development for the treatment of cardiovascular diseases. Here, we assessed the potential for pharmacokinetic drug-drug interaction of LCZ696 (400 mg, single dose or once daily [q.d.]) when co-administered with omeprazole 40 mg q.d. (n = 28) or metformin 1000 mg q.d. (n = 27) or levonorgestrel-ethinyl estradiol 150/30 μg single dose (n = 24) in three separate open-label, single-sequence studies in healthy subjects. Pharmacokinetic parameters of LCZ696 analytes (sacubitril, LBQ657, and valsartan), metformin, and levonorgestrel-ethinyl estradiol were assessed. Omeprazole did not alter the AUCinf of sacubitril and pharmacokinetics of LBQ657; however, 7% decrease in the Cmax of sacubitril, and 11% and 13% decreases in AUCinf and Cmax of valsartan were observed. Co-administration of LCZ696 with metformin had no significant effect on the pharmacokinetics of LBQ657 and valsartan; however, AUCtau,ss and Cmax,ss of metformin were decreased by 23%.
2. Interactions of omeprazole-based analogues with cytochrome P450 2C19: a computational study.
Li J1, Du H1, Wu Z1, Su H1, Liu G1, Tang Y1, Li W1. Mol Biosyst. 2016 Apr 21.
Cytochrome P450 2C19 (CYP2C19) is one of 57 drug metabolizing enzymes in humans and is responsible for the metabolism of ∼7-10% of drugs in clinical use. Recently omeprazole-based analogues were reported to be the potent inhibitors of CYP2C19 and have the potential to be used as the tool compounds for studying the substrate selectivity of CYP2C19. However, the binding modes of these compounds with CYP2C19 remain to be elucidated. In this study, a combination of molecular docking, molecular dynamics (MD), and MM/GBSA calculations was employed to systematically investigate the interactions between these compounds and CYP2C19. The binding modes of these analogues were analyzed in detail. The results indicated that the inclusion of explicit active site water molecules could improve binding energy prediction when the water molecules formed a hydrogen bonding network between the ligand and protein. We also found that the effect of active site water molecules on binding free energy prediction was dependent on the ligand binding modes.
Spectrum
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
1H NMR Spectrum
Experimental Conditions
Sample Concentration: 25.0 mM
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus: 1H
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus: 1H
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
[1H,13C] 2D NMR Spectrum
Experimental Conditions
Sample Concentration: 25.0 mM
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
