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496100

Sigma-Aldrich

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

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About This Item

Empirische Formel (Hill-System):
C17H19N3O3S
CAS-Nummer:
73590-58-6
Molekulargewicht:
345.42
MDL-Nummer:
MFCD00083192
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥94% (HPLC)

Form

solid

Hersteller/Markenname

Calbiochem®

Lagerbedingungen

OK to freeze
protect from light

Farbe

tan to off-white

Löslichkeit

DMSO: 25 mg/mL

Kationenspuren

heavy metals: ≤20 ppm

Versandbedingung

ambient

Lagertemp.

2-8°C

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)

InChIKey

SUBDBMMJDZJVOS-UHFFFAOYSA-N

Allgemeine Beschreibung

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. Wirkung

Cell permeable: yes
Primary Target
proton pump
Product does not compete with ATP.
Reversible: no

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Irritant (B)

Rekonstituierung

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

Sonstige Hinweise

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.

Rechtliche Hinweise

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

Piktogramme

Exclamation markEnvironment
GHS07,GHS09

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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E Fellenius et al.
Nature, 290(5802), 159-161 (1981-03-12)
Studies both in vivo and in vitro have shown that substituted benzimidazoles inhibit the stimulation of acid secretion produced by dibutyryl cyclic AMP and histamine. Furthermore, the results differ from those produced by H2 antagonists and anticholinergic agents in that
G Sachs et al.
Annual review of pharmacology and toxicology, 35, 277-305 (1995-01-01)
The gastric H+,K+ ATPase--the gastric acid pump--is the molecular target for the class of antisecretory drugs called the proton-pump inhibitors (PPIs). These compounds--omeprazole, lansoprazole, and pantoprazole--contain, as their core structure, 2-pyridyl methylsulfinyl benzimidazole. The H+,K+ ATPase is a heterodimer composed
M Besancon et al.
The Journal of biological chemistry, 272(36), 22438-22446 (1997-09-05)
The vesicular gastric H,K-ATPase catalyzes an electroneutral H for K exchange allowing acidification of the intravesicular space. There is a total of 28 cysteines present in the alpha subunit of the gastric H,K-ATPase, of which 10 are found in the
N Lambrecht et al.
The Journal of biological chemistry, 275(6), 4041-4048 (2000-02-08)
The gastric H,K-ATPase is covalently inhibited by substituted pyridyl-methylsulfinyl-benzimidazoles, such as omeprazole, that convert to thiophilic probes of luminally accessible cysteines in the acid space. The K(+) competitive inhibitor, SCH28080, prevented inhibition of acid transport by omeprazole. In stably expressing
D Diaz et al.
Gastroenterology, 99(3), 737-747 (1990-09-01)
Omeprazole is a new drug used for its high efficiency as an inhibitor of gastric acid secretion. This substituted benzimidazole molecule had been shown to decrease several liver cytochrome P450-mediated monooxygenase activities both in vitro and in vivo. The present

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