Omeprazole
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Basic Info
| Common Name | Omeprazole(F04851) |
| 2D Structure | |
| Description | Omeprazole is a highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers, dyspepsia, peptic ulcer disease , gastroesophageal reflux disease and Zollinger-Ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of Gastric Parietal Cells.--Pubchem. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries. |
| FRCD ID | F04851 |
| CAS Number | 73590-58-6 |
| PubChem CID | 4594 |
| Formula | C17H19N3O3S |
| IUPAC Name | 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole |
| InChI Key | SUBDBMMJDZJVOS-UHFFFAOYSA-N |
| 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) |
| Canonical SMILES | CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC |
| Isomeric SMILES | CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC |
| Wikipedia | Omeprazole |
| Synonyms |
Prilosec
Omepral
omeprazole
73590-58-6
Losec
Antra
Esomeprazole
Omeprazon
Audazol
Omapren
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzimidazoles |
| Subclass | Sulfinylbenzimidazoles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Sulfinylbenzimidazoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Sulfinylbenzimidazole - Anisole - Alkyl aryl ether - Methylpyridine - Pyridine - Benzenoid - Azole - Imidazole - Heteroaromatic compound - Sulfoxide - Azacycle - Ether - Sulfinyl compound - Organic nitrogen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 345.417 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Complexity | 453 |
| Monoisotopic Mass | 345.115 |
| Exact Mass | 345.115 |
| XLogP | 2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.6326 |
| Human Intestinal Absorption | HIA+ | 0.9968 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Non-substrate | 0.5573 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6622 |
| Non-inhibitor | 0.9680 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5420 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6448 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7838 |
| CYP450 2D6 Substrate | Substrate | 0.6175 |
| CYP450 3A4 Substrate | Substrate | 0.6901 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7505 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8994 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7960 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7895 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7190 |
| Non-inhibitor | 0.8977 | |
| AMES Toxicity | Non AMES toxic | 0.5692 |
| Carcinogens | Non-carcinogens | 0.8318 |
| Fish Toxicity | High FHMT | 0.9479 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7285 |
| Honey Bee Toxicity | High HBT | 0.6148 |
| Biodegradation | Not ready biodegradable | 0.9778 |
| Acute Oral Toxicity | III | 0.7790 |
| Carcinogenicity (Three-class) | Warning | 0.5255 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8787 | LogS |
| Caco-2 Permeability | 1.7040 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2254 | LD50, mol/kg |
| Fish Toxicity | 1.2929 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4349 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| To Flavor or Not to Flavor Extemporaneous Omeprazole Liquid. | Int J Pharm Compd | 2017 Nov-Dec | 29220339 |
| A pilot study comparing the effect of orally administered esomeprazole andomeprazole on gastric fluid pH in horses. | N Z Vet J | 2017 Nov | 28738738 |
| Phytochemicals enhance antioxidant enzyme expression to protect against NSAID-induced oxidative damage of the gastrointestinal mucosa. | Mol Nutr Food Res | 2017 Jun | 27883262 |
| Pericarditis caused by Campylobacter fetus subspecies fetus associated withingestion of raw beef liver. | J Infect Chemother | 2017 Dec | 28803866 |
| Pharmacological interventions for acute pancreatitis. | Cochrane Database Syst Rev | 2017 Apr 21 | 28431202 |
| The effects of dose and diet on the pharmacokinetics of omeprazole in the horse. | J Vet Pharmacol Ther | 2017 Apr | 27478135 |
| The Effects of Synbiotic "Bifidobacterium lactis B94 plus Inulin" Addition onStandard Triple Therapy of Helicobacter pylori Eradication in Children. | Can J Gastroenterol Hepatol | 2017 | 28656129 |
| Role of Quantitative Clinical Pharmacology in Pediatric Approval and Labeling. | Drug Metab Dispos | 2016 Jul | 27079249 |
| Acute Coronary Syndromes, Gastrointestinal Protection, and RecommendationsRegarding Concomitant Administration of Proton-Pump Inhibitors(Omeprazol/Esomeprazole) and Clopidogrel. | Am J Cardiol | 2016 Feb 1 | 26708640 |
| Investigation of the effect of food and omeprazole on the relativebioavailability of a single oral dose of 240 mg faldaprevir, a selectiveinhibitor of HCV NS3/4 protease, in an open-label, randomized, three-waycross-over trial in healthy participants. | J Pharm Pharmacol | 2016 Apr | 27019158 |
| Dietary Inulin Fibers Prevent Proton-Pump Inhibitor (PPI)-Induced Hypocalcemia inMice. | PLoS One | 2015 Sep 23 | 26397986 |
| Metabolism of (-)-cis- and (-)-trans-rose oxide by cytochrome P450 enzymes inhuman liver microsomes. | Biopharm Drug Dispos | 2015 Dec | 26126958 |
| Treatment of Helicobacter Pylori infection: optimization strategies in a highresistance era. | Expert Opin Pharmacother | 2015 | 26330278 |
| Effect of Pretreatment with Lactobacillus delbrueckii and Streptococcusthermophillus on Tailored Triple Therapy for Helicobacter pylori Eradication: AProspective Randomized Controlled Clinical Trial. | Asian Pac J Cancer Prev | 2015 | 26163609 |
| [Clinical effect of triple therapy combined with Saccharomyces boulardii in thetreatment of Helicobacter pylori infection in children]. | Zhongguo Dang Dai Er Ke Za Zhi | 2014 Mar | 24661511 |
| Effect of meal and antisecretory agents on the pharmacokinetics ofdanoprevir/ritonavir in healthy volunteers. | J Pharm Pharmacol | 2014 Jan | 24117531 |
| Drug-drug interactions between sucroferric oxyhydroxide and losartan, furosemide,omeprazole, digoxin and warfarin in healthy subjects. | J Nephrol | 2014 Dec | 24699894 |
| Omeprazole improves the anti-obesity and antidiabetic effects of exendin-4 in db/db mice (-4 db/db)*. | J Diabetes | 2013 Jun | 22830490 |
| The effects of multistrain probiotic compound on bismuth-containing quadrupletherapy for Helicobacter pylori infection: a randomized placebo-controlledtriple-blind study. | Helicobacter | 2013 Aug | 23433200 |
| [Lactobacillus rhamnosus GG supplementation to reduce side-effects ofanti-Helicobacter pylori treatment]. | Rev Gastroenterol Peru | 2013 Apr-Jun | 23838939 |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Afzelius L, Zamora I, Masimirembwa CM, Karlen A, Andersson TB, Mecucci S, Baroni M, Cruciani G: Conformer- and alignment-independent model for predicting structurally diverse competitive CYP2C9 inhibitors. J Med Chem. 2004 Feb 12;47(4):907-14. [14761192 ]
- General Function:
- Hydrogen:potassium-exchanging atpase activity
- Specific Function:
- Required for stabilization and maturation of the catalytic proton pump alpha subunit and may also involved in cell adhesion and establishing epithelial cell polarity.
- Gene Name:
- ATP4B
- Uniprot ID:
- P51164
- Molecular Weight:
- 33366.95 Da
References
- Sanfilippo PJ, Urbanski M, Press JB, Hajos ZG, Shriver DA, Scott CK: Synthesis of (aryloxy)alkylamines. 1. Novel antisecretory agents with H+K+-ATPase inhibitory activity. J Med Chem. 1988 Sep;31(9):1778-85. [2842503 ]
- General Function:
- Xenobiotic-transporting atpase activity
- Specific Function:
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name:
- ABCB1
- Uniprot ID:
- P08183
- Molecular Weight:
- 141477.255 Da
References
- Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [11770010 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
- Gene Name:
- ATP4A
- Uniprot ID:
- P20648
- Molecular Weight:
- 114117.74 Da
- Mechanism of Action:
- Omeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H<sup>+</sup>/K<sup>+</sup>-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.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Dzeletovic N, McGuire J, Daujat M, Tholander J, Ema M, Fujii-Kuriyama Y, Bergman J, Maurel P, Poellinger L: Regulation of dioxin receptor function by omeprazole. J Biol Chem. 1997 May 9;272(19):12705-13. [9139728 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Roy K, Pratim Roy P: Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques. Eur J Med Chem. 2009 Jul;44(7):2913-22. doi: 10.1016/j.ejmech.2008.12.004. Epub 2008 Dec 16. [19128860 ]