O104

Omeprazole

≥98% (HPLC), solid, gastric secretion inhibitor

• Synonym(s): 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, Antra, Losec
• Empirical Formula (Hill Notation): C₁₇H₁₉N₃O₃S
• CAS Number: 73590-58-6
• Molecular Weight: 345.42
• MDL number: MFCD00083192
• UNSPSC Code: 12352200
• PubChem Substance ID: 24897870
• NACRES: NA.77

Properties

• product name: Omeprazole, solid
• form: solid
• color: white
• solubility: H₂O: 0.5 mg/mL; DMSO: >19 mg/mL; ethanol: 4.5 mg/mL
• originator: AstraZeneca
• storage temp.: 2-8°C
• SMILES string: COc1ccc2[nH]c(nc2c1)S(=O)Cc3ncc(C)c(OC)c3C
• 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
• Gene Information: human ... ABCB1(5243) , ATP4A(495) , ATP4B(496) , CYP1A2(1544)

Description

General description

Omeprazole is a benzimidazole derivative, a weak base and is lipophilic in nature. This compound is pH sensitive and does not exists in its original form at low pH.

Application

Omeprazole has been used as an atypical cytochrome P450 (CYP) 1A2 inducer in Dulbecco′s modified eagle′s medium (serum free) to study the effects of inducers on CYP activities in human hepatocytes and also to compare with other classical aryl hydrocarbon receptor ligands.

Biochem/physiol Actions

Omeprazole binds covalently to proton pump (H⁺, K⁺-ATPase) and inhibits gastric secretion. It is useful in ameliorating the effects of peptic oesophagitis, duodenal and gastric ulcer. Omeprazole is preferred over antagonists of histamine H2-receptor and ranitidine for its higher efficiency. It is also useful in treating Zollinger-Ellison syndrome.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Caution

Hygroscopic, photosensitive

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H302,H317,H411
• Precautionary Statements: P261 - P264 - P273 - P280 - P301 + P312 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves