496100

Omeprazole

A cell-permeable pyridyl methylsulfinyl benzimidazole compound that acts as selective proton pump inhibitor.

• Synonym(s): Omeprazole, H 168/68, 5-Methoxy-2[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole
• Empirical Formula (Hill Notation): C₁₇H₁₉N₃O₃S
• CAS Number: 73590-58-6
• Molecular Weight: 345.42
• MDL number: MFCD00083192
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• description: Merck USA index - 14, 6845
• Assay: ≥94% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: tan to off-white
• solubility: DMSO: 25 mg/mL
• cation traces: heavy metals: ≤20 ppm
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [S+]([O-])(Cc3ncc(c(c3C)OC)C)c1[nH]c2c(n1)cc(cc2)OC
• 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

Description

General description

A cell-permeable pyridyl methylsulfinyl benzimidazole compound that acts as selective proton pump inhibitor. Behaves as a prodrug by undergoing an acid-catalyzed rearrangement to a thiol-reactive cationic sulfenamide that inhibits (H⁺, K⁺)-ATPase in the gastric milieu. An aryl hydrocarbon-like inducer of cytochrome P450 secretion in human liver.

A cell-permeable, selective proton pump inhibitor. Behaves as a prodrug by undergoing an acid-catalyzed rearrangement to a thiol-reactive cationic sulfenamide that inhibits (H⁺-K⁺)-ATPase in the gastric milieu. Also acts as an aryl hydrocarbon-like inducer of cytochrome P450 secretion in human liver.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
proton pump

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Lambrecht, N., et al. 2000. J. Biol. Chem.275, 4041.
Besancon, M., et al. 1997. J. Biol. Chem.272, 22438.
Sachs, G., et al. 1995. Ann. Rev. Pharmacol. Toxicol.35, 277.
Diaz, D., et al. 1990. Gastroenterology99, 737.
Fellenius, E., et al. 1981. Nature290, 159.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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