Omeprazole

Base Information

• Chemical Name: Omeprazole
• CAS No.: 73590-58-6
• Deprecated CAS: 172964-80-6,131959-78-9,131959-78-9
• Molecular Formula: C17H19N3O3S
• Molecular Weight: 345.422
• Hs Code.: 29333990
• European Community (EC) Number: 615-996-8,620-470-6,623-285-9
• NSC Number: 759192,751450
• UNII: KG60484QX9
• DSSTox Substance ID: DTXSID6021080
• Nikkaji Number: J33.884B
• Wikipedia: Omeprazole
• Wikidata: Q422210
• NCI Thesaurus Code: C74598,C65538,C65539,C66256,C716
• RXCUI: 7646,236486,283742,1294569,1792108
• Pharos Ligand ID: 32ATJZBGT8TF
• Metabolomics Workbench ID: 145082
• ChEMBL ID: CHEMBL1503
• Mol file: 73590-58-6.mol

Synonyms:H 168 68;H 168-68;H 16868;Magnesium, Omeprazole;Omeprazole;Omeprazole Magnesium;Omeprazole Sodium;Prilosec;Sodium, Omeprazole

Chemical Property of Omeprazole

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 156 °C
• Boiling Point: 599.991 °C at 760 mmHg
• PKA: pKa 4.14/8.9(H2O,t =25,I=0.025) (Uncertain)
• Flash Point: 316.663 °C
• PSA: 96.31000
• Density: 1.371 g/cm³
• LogP: 3.76540
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.5 mg/mL
• Water Solubility.: Soluble in water (0.5 mg/ml), DMSO (25 mg/ml), and ethanol (4.5 mg/ml).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 345.11471265
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

99% ^*data from raw suppliers

Omeprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiulcer Agents
• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
• Recent ClinicalTrials: Recurrence Rate Comparison Between Esomeprazole and Lansoprazole in Eradicating Helicobacter Pylori Infection Among Children
• Recent EU Clinical Trials: 'A Phase III Study to Assess the Efficacy and Safety of NEXIUM for Maintenance of Healing of Erosive Esophagitis in Pediatric Patients 1 to 11 Years of Age'
• Recent NIPH Clinical Trials: V-POINT study
• Mechanism of Action: Omeprazole is a proton pump inhibitor (PPI) that inhibits the H+/K+ ATPase in gastric cells, reducing proton secretion into the gastric lumen. It also inhibits vacuolar ATPase (V-ATPase), potentially exerting antiproliferative effects in tumor cells.
• Medical Uses: Used to treat various gastrointestinal disorders such as gastroesophageal reflux disease (GERD), gastric ulcers, duodenal ulcers, upper gastrointestinal (GI) tract inflammatory conditions, eosinophilic esophagitis, and erosive esophagitis. Also employed in the treatment of hypersecretory conditions like Zollinger-Ellison syndrome. Combined with antibiotics for eradicating Helicobacter pylori (H. pylori).
• Pharmacokinetics: Metabolized primarily by the CYP2C19 enzyme. Response to omeprazole can vary based on CYP2C19 metabolizer status, with rapid metabolizers potentially needing higher doses for efficacy and poor metabolizers requiring lower doses. Dosing recommendations vary among different metabolizer phenotypes, with ultrarapid metabolizers potentially needing increased doses for H. pylori eradication.
• Global Variation in Metabolizer Phenotypes: Frequencies of CYP2C19 metabolizer phenotypes differ among global populations, with implications for dosing.
• Pharmacogenetics Recommendations: Dutch Pharmacogenetics Working Group (DPWG) recommends dose adjustments for different metabolizer phenotypes.; Clinical Pharmacogenetics Implementation Consortium (CPIC) suggests increased doses for ultrarapid and rapid metabolizers and reduced dosages for intermediate and poor metabolizers for chronic therapy.
• Superiority in Acid Inhibition: Omeprazole is a potent inhibitor of gastric acid secretion, demonstrating superiority over previous treatments for GERD and peptic ulcers. It concentrates specifically in the acidic canalicular space of parietal cells where it inhibits the proton pump.
• Research on Antiproliferative Effects: Omeprazole has shown inhibition of pancreatic cancer cell growth and promotion of apoptosis in human melanoma cells and B-cell malignancies.

Technology Process of Omeprazole

There total 32 articles about Omeprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 6-methoxy-1H-benzoimidazole-2-thiol (37052-78-1) → omeprazole (73590-58-6)

Guidance literature:

6-methoxy-1H-benzoimidazole-2-thiol; With sodium hydroxide; In ethanol; water; at 70 - 90 ℃;

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride; With hydrogenchloride; In ethanol; water; at -10 - 30 ℃; for 4h; Reflux;

Reference yield: 91.0%

omeprazole sulfide (73590-85-9) → omeprazole (73590-58-6)

Guidance literature:

With dihydrogen peroxide; molybdenyl acetylacetonate; In methanol; water; at 0 - 5 ℃; for 3h;

Reference yield: 86.0%

(-)-menthyl 5-methoxy-2-benzimidazolylsulphinate (1080503-61-2) + 4-methoxy-2,3,5-trimethylpyridine (109371-19-9) → omeprazole (73590-58-6)

Guidance literature:

4-methoxy-2,3,5-trimethylpyridine; With n-butyllithium; In tetrahydrofuran; at -90 - -80 ℃; for 0.5h;

(-)-menthyl 5-methoxy-2-benzimidazolylsulphinate; In tetrahydrofuran; at -80 - -20 ℃;

With water; In tetrahydrofuran; at -20 ℃;

upstream raw materials:

omeprazole sulfide

5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole

Diethyl tartrate

diethyl (2S,3S)-tartrate

Downstream raw materials:

4-methoxy-2,3,5-trimethylpyridine

6-methoxy-1H-benzoimidazole-2-thiol

(R)-omeprazole

esomeprazole

Refernces

• 1、 Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele. "A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent". supporting information. p. 156 - 161. Retrieved 2021/01/14.
• 2、 -. "Preparation method of omeprazole and omeprazole". Paragraph 0049-0084. . Retrieved 2021/04/21.