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O104

Sigma-Aldrich

Omeprazole

solid

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Synonym(s):
5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, Antra, Losec
Empirical Formula (Hill Notation):
C17H19N3O3S
CAS Number:
Molecular Weight:
345.42
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

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

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This Item
PHR10591478505Y0001042
Omeprazole solid

Sigma-Aldrich

O104

Omeprazole

Omeprazole Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1059

Omeprazole

Omeprazole United States Pharmacopeia (USP) Reference Standard

USP

1478505

Omeprazole

color

white

color

-

color

-

color

-

solubility

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

solubility

-

solubility

-

solubility

-

originator

AstraZeneca

originator

-

originator

-

originator

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Gene Information

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

Gene Information

human ... ATP4A(495), ATP4B(496)

Gene Information

human ... ATP4A(495), ATP4B(496)

Gene Information

human ... ATP4A(495), ATP4B(496)

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

Signal Word

Warning

Hazard Statements

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

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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)
Chaitra Prabhakara et al.
PLoS pathogens, 17(7), e1009706-e1009706 (2021-07-13)
Many viruses utilize the host endo-lysosomal network for infection. Tracing the endocytic itinerary of SARS-CoV-2 can provide insights into viral trafficking and aid in designing new therapeutic strategies. Here, we demonstrate that the receptor binding domain (RBD) of SARS-CoV-2 spike
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)
Un-Ho Jin et al.
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