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Key Documents

496100

Sigma-Aldrich

Omeprazole

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

别名:

Omeprazole, H 168/68, 5-Methoxy-2[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole

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About This Item

经验公式(希尔记法):
C17H19N3O3S
CAS号:
分子量:
345.42
MDL號碼:
分類程式碼代碼:
12352200
NACRES:
NA.77

品質等級

化驗

≥94% (HPLC)

形狀

solid

製造商/商標名

Calbiochem®

儲存條件

OK to freeze
protect from light

顏色

tan to off-white

溶解度

DMSO: 25 mg/mL

正離子痕跡

heavy metals: ≤20 ppm

運輸包裝

ambient

儲存溫度

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)

InChI 密鑰

SUBDBMMJDZJVOS-UHFFFAOYSA-N

一般說明

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.

生化/生理作用

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

包裝

Packaged under inert gas

警告

Toxicity: Irritant (B)

重構

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

其他說明

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.

法律資訊

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

象形圖

Exclamation markEnvironment

訊號詞

Warning

危險聲明

危險分類

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

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 2

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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
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

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