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O104

Sigma-Aldrich

Omeprazole

≥98% (HPLC), solid, gastric secretion inhibitor

Synonym(s):

5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, Antra, Losec

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About This Item

Empirical Formula (Hill Notation):
C17H19N3O3S
CAS Number:
73590-58-6
Molecular Weight:
345.42
MDL number:
MFCD00083192
UNSPSC Code:
12352200
PubChem Substance ID:
24897870
NACRES:
NA.77

product name

Omeprazole, solid

form

solid

color

white

solubility

H2O: 0.5 mg/mL
DMSO: >19 mg/mL
ethanol: 4.5 mg/mL

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

COc1ccc2[nH]c(nc2c1)S(=O)Cc3ncc(C)c(OC)c3C

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

Gene Information

human ... ABCB1(5243) , ATP4A(495) , ATP4B(496) , CYP1A2(1544)

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General description

Omeprazole is a benzimidazole derivative, a weak base and is lipophilic in nature. This compound is pH sensitive and does not exists in its original form at low pH.

Application

Omeprazole has been used as an atypical cytochrome P450 (CYP) 1A2 inducer in Dulbecco′s modified eagle′s medium (serum free) to study the effects of inducers on CYP activities in human hepatocytes and also to compare with other classical aryl hydrocarbon receptor ligands.

Biochem/physiol Actions

Omeprazole binds covalently to proton pump (H+, K+-ATPase) and inhibits gastric secretion. It is useful in ameliorating the effects of peptic oesophagitis, duodenal and gastric ulcer. Omeprazole is preferred over antagonists of histamine H2-receptor and ranitidine for its higher efficiency. It is also useful in treating Zollinger-Ellison syndrome.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Caution

Hygroscopic, photosensitive

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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The induction of CYP1A2, CYP2D6 and CYP3A4 by six trade herbal products in cultured primary human hepatocytes
Hellum BH, et al.
Basic and clinical neuroscience, 100(1), 23-30 (2007)
Omeprazole
S. Holt and C. W. Howden
Drugs, 36(4), 385?393-385?393 (1991)
Un-Ho Jin et al.
Cancers, 12(8) (2020-08-01)
Background: The aryl hydrocarbon receptor (AhR) is expressed in gliomas and the highest staining is observed in glioblastomas. A recent study showed that the AhR exhibited tumor suppressor-like activity in established and patient-derived glioblastoma cells and genomic analysis showed that
Profiling the hepatic effects of flutamide in rats: A microarray comparison with classical AhR ligands and atypical CYP1A inducers
Coe KJ, et al.
Drug Metabolism and Disposition (2006)
S E Attwood et al.
Alimentary pharmacology & therapeutics, 41(11), 1162-1174 (2015-04-11)
Control of chronic gastro-oesophageal reflux disease may be achieved either by anti-reflux surgery (ARS) or by long-term medical therapy with proton pump inhibitors (PPIs). The primary efficacy results of the SOPRAN study, comparing long-term omeprazole use with open ARS, and
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Chromatograms

application for HPLC

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