496100
Omeprazole
A cell-permeable pyridyl methylsulfinyl benzimidazole compound that acts as selective proton pump inhibitor.
Sinonimo/i:
Omeprazole, H 168/68, 5-Methoxy-2[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole
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About This Item
Formula empirica (notazione di Hill):
C17H19N3O3S
Numero CAS:
Peso molecolare:
345.42
Numero MDL:
Codice UNSPSC:
12352200
NACRES:
NA.77
Prodotti consigliati
Livello qualitativo
Saggio
≥94% (HPLC)
Forma fisica
solid
Produttore/marchio commerciale
Calbiochem®
Condizioni di stoccaggio
OK to freeze
protect from light
Colore
tan to off-white
Solubilità
DMSO: 25 mg/mL
Cationi in tracce
heavy metals: ≤20 ppm
Condizioni di spedizione
ambient
Temperatura di conservazione
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)
SUBDBMMJDZJVOS-UHFFFAOYSA-N
Descrizione generale
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.
Azioni biochim/fisiol
Cell permeable: yes
Primary Target
proton pump
proton pump
Product does not compete with ATP.
Reversible: no
Confezionamento
Packaged under inert gas
Attenzione
Toxicity: Irritant (B)
Ricostituzione
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Altre note
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.
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.
Note legali
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Avvertenze
Warning
Indicazioni di pericolo
Consigli di prudenza
Classi di pericolo
Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1
Codice della classe di stoccaggio
11 - Combustible Solids
Classe di pericolosità dell'acqua (WGK)
WGK 2
Punto d’infiammabilità (°F)
Not applicable
Punto d’infiammabilità (°C)
Not applicable
Certificati d'analisi (COA)
Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.
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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
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
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
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
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
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