An active metabolite of omeprazole
Related Products
Labeled Version(s)
40260Omeprazole sulfide-d3
Parent Compound(s)
14880Omeprazole
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Omeprazole sulfide

Item No. 18885

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole
CAS Number
73590-85-9
Synonyms
  • ​OMEP sulfide
  • OMP sulfide
  • OMZ sulfide
  • Pyrmetazole
  • Ufiprazole
Molecular Formula
C17H19N3O2S
Formula Weight
329.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 30 mg/mlEthanol: 25 mg/ml
λmax
300 nm
SMILES
COC1=CC=C2C(N=C(SCC3=C(C)C(OC)=C(C)C=N3)N2)=C1
InChi Code
InChI=1S/C17H19N3O2S/c1-10-8-18-15(11(2)16(10)22-4)9-23-17-19-13-6-5-12(21-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
InChi Key
XURCIPRUUASYLR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Omeprazole sulfide is an active metabolite of the gastric H+/K+ ATPase inhibitor omeprazole (Item No. 14880).1,2 Omeprazole sulfide has been used as a precursor in the synthesis of the H+/K+ ATPase inhibitor esomeprazole (Item No. 17303).3 It is also a potential impurity in commercial preparations of omeprazole.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoffmann, K.J. Identification of the main urinary metabolites of omeprazole after an oral dose to rats and dogs. Drug Metab. Dispos. 14(3), 341-348 (1986).

    2. Ogilvie, B.W., Yerino, P., Kazmi, F., et al. The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: Implications for coadministration with clopidogrel. Drug Metab. Dispos. 39(11), 2020-2033 (2011).

    3. Cotton, H., Elebring, T., Larsson, M., et al. Asymmetric synthesis of esomeprazole. Tetrahedron Asymmetry 11(18), 3819-3825 (2000).

    4. Iuga, C., Bojiţă, M., and Leucuţa, S.E. Development of a validated RP-HPLC method for separation and determination of process-related impurities of omeprazole in bulk drugs. Farmacia 57(5), 534-541 (2009).