An internal standard for the quantification of omeprazole
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Unlabeled Version(s)
14880Omeprazole
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Omeprazole-d3

Item No. 22087

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole-4,5,7-d3
CAS Number
934293-92-2
Synonyms
  • OMEP-d3
  • OMP-d3
  • OMZ-d3
Molecular Formula
C17H16D3N3O3S
Formula Weight
348.4
Purity
≥99% deuterated forms (d1-d3); ≤1% d0
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 5 mg/ml
SMILES
COC1=C([2H])C([2H])=C2C(N=C(S(CC3=C(C)C(OC)=C(C)C=N3)=O)N2)=C1[2H]
InChi Code
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)/i5D,6D,7D
InChi Key
SUBDBMMJDZJVOS-CRSPMMAGSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    Omeprazole-d3 is intended for use as an internal standard for the quantification of omeprazole (Item No. 14880) by GC- or LC-MS. Omeprazole is an inhibitor of gastric H+/K+ ATPase (IC50 = 1.1 µM for the pig ATPase).1 It is a racemic mixture of esomeprazole (Item No. 17303) and (R)-omeprazole (Item No. 18874).2 Omeprazole (100 µM) decreases zymosan-induced oxygen free radical production in isolated human neutrophils.3 It is active against 17 strains of H. pylori (MIC50s = 12.5-50 µg/ml).4 It decreases histamine-induced acid secretion in dogs (ED50 = 0.35 µmol/kg).5 Formulations containing omeprazole have been used in the treatment of duodenal and gastric ulcers, gastroesophageal reflux disease, and erosive esophagitis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Smolka, A.J., Goldenring, J.R., Gupta, S., et al. Inhibition of gastric H,K-ATPase activity and gastric epithelial cell IL-8 secretion by the pyrrolizine derivative ML 3000. BMC Gastroenterol. 4(4), (2004).

    2. Lind, T., Rydberg, L., Kylebäck, A., et al. Esomeprazole provides improved acid control vs. omeprazole in patients with symptoms of gastro-oesophageal reflux disease. Aliment. Pharmacol. Ther. 14(7), 861-867 (2000).

    3. Suzuki, M., Mori, M., Miura, S., et al. Omeprazole attenuates oxygen-derived free radical production from human neutrophils. Free Radic. Biol. Med. 21(5), 727-731 (1996).

    4. Iwahi, T., Satoh, H., Nakao, M., et al. Lansoprazole, a novel benzimidazole proton pump inhibitor, and its related compounds have selective activity against Helicobacter pylori. Antimicrob. Agents Chemother. 35(3), 490-496 (1991).

    5. Larsson, H., Carlsson, E., Junggren, U., et al. Inhibition of gastric acid secretion by omeprazole in the dog and rat. Gastroenterology 85(4), 900-907 (1983).

    Product Citations

    Shin, S.-H., Park, Y., Park, M.-H., et al. Profiling and indentification of omeprazole metabolites in mouse brain and plasma by isotope ratio-monitoring liquid chromatography-mass spectrometric method. Life 10, 115 (2020).