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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

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About This Item

Empirical Formula (Hill Notation):
C17H19N3O3S
CAS Number:
73590-58-6
Molecular Weight:
345.42
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00083192
Assay:
≥94% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light
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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

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)

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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