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O0151000

Omeprazole impurity D

Name: Omeprazole impurity D
Brand: SIAL

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Omeprazole sulfone, 5-Methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfonyl}-1H-benzimidazole, Omeprazole sulphone

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₉N₃O₄S

CAS Number:

88546-55-8

Molecular Weight:

361.42

Beilstein:

8347309

MDL number:

MFCD00869772

UNSPSC Code:

41116107

PubChem Substance ID:

329818824

NACRES:

NA.24

grade

pharmaceutical primary standard

API family

omeprazole

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

O=S(C1=NC2=CC(OC)=CC=C2N1)(CC3=NC=C(C)C(OC)=C3C)=O

InChI

1S/C17H19N3O4S/c1-10-8-18-15(11(2)16(10)24-4)9-25(21,22)17-19-13-6-5-12(23-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

InChI key

IXEQEYRTSRFZEO-UHFFFAOYSA-N

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Analytical Reference Standards

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Omeprazole impurity D EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

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Pictograms

GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H411

Precautionary Statements

P264 - P270 - P273 - P301 + P312 - P391 - P501

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Formation of omeprazole sulphone but not 5-hydroxyomeprazole is inhibited by grapefruit juice.

W Tassaneeyakul et al.

British journal of clinical pharmacology, 49(2), 139-144 (2000-02-15)

To determine the effect of grapefruit juice on omeprazole metabolism in vivo. This was a randomized crossover study with a 2 week washout period. Omeprazole (20 mg) was taken orally by 13 healthy volunteers after an overnight fast with either

Assay of omeprazole and omeprazole sulfone by semi-microcolumn liquid chromatography with mixed-function precolumn.

D S Yim et al.

Journal of chromatography. B, Biomedical sciences and applications, 754(2), 487-493 (2001-05-08)

A column-switching system based on semi-microcolumns was used for direct analysis of omeprazole and omeprazole sulfone in human plasma samples. Plasma samples were injected into a mixed-function (MF Ph-1) column (35 mmx4.6 mm I.D.) to remove proteins and other non-specific

5-hydroxylation of omeprazole by human liver microsomal fractions from Chinese populations related to CYP2C19 gene dose and individual ethnicity.

Y Shu et al.

The Journal of pharmacology and experimental therapeutics, 295(2), 844-851 (2000-10-25)

It has been previously reported that omeprazole (OP) oxidation is mediated by CYP2C19 and CYP3A4 in human livers. In this study, we assessed their relative contributions with human liver microsomal fractions from Chinese populations that were genotyped by CYP2C19 and

Determination of esomeprazole and its two main metabolites in human, rat and dog plasma by liquid chromatography with tandem mass spectrometry.

Ia Hultman et al.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 848(2), 317-322 (2006-12-05)

A LC-MS/MS method was developed for quantitative determination of esomeprazole, and its two main metabolites 5-hydroxyesomeprazole and omeprazole sulphone in 25 microL human, rat or dog plasma. The analytes and their internal standards were extracted from plasma into methyl tert-butyl

Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes.

A Abelö et al.

Drug metabolism and disposition: the biological fate of chemicals, 28(8), 966-972 (2000-07-20)

This study demonstrates the stereoselective metabolism of the optical isomers of omeprazole in human liver microsomes. The intrinsic clearance (CL(int)) of the formation of the hydroxy metabolite from S-omeprazole was 10-fold lower than that from R-omeprazole. However, the CL(int) value

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