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O104

Sigma-Aldrich

Omeprazole

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C17H19N3O3S
Numéro CAS:
73590-58-6
Poids moléculaire :
345.42
Numéro MDL:
MFCD00083192
Code UNSPSC :
12352200
ID de substance PubChem :
24897870
Nomenclature NACRES :
NA.77

product name

Omeprazole, solid

Forme

solid

Couleur

white

Solubilité

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

Auteur

AstraZeneca

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

SUBDBMMJDZJVOS-UHFFFAOYSA-N

Informations sur le gène

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

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Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Attention

Hygroscopic, photosensitive

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H302,H317,H411

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Omeprazole
S. Holt and C. W. Howden
Drugs, 36(4), 385?393-385?393 (1991)
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)
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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