496100

Omeprazole

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

• Synonym(e): Omeprazole, H 168/68, 5-Methoxy-2[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole
• Empirische Formel (Hill-System): C₁₇H₁₉N₃O₃S
• CAS-Nummer: 73590-58-6
• Molekulargewicht: 345.42
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00083192
• Assay: ≥94% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Eigenschaften

• Quality Segment: 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

Beschreibung

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

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Sicherheitshinweise

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H317,H411
• pcodes: P261 - P264 - P273 - P280 - P301 + P312 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable