A potential impurity found in commercial omeprazole and esomeprazole magnesium preparations
Related Products
Isomer(s)
354484-hydroxy Omeprazole sulfide
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4-desmethoxy Omeprazole

Item No. 22122

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-6-methoxy-1H-benzimidazole
CAS Number
110374-16-8
Synonyms
  • 4-desmethoxy OMEP
  • 4-desmethoxy OMP
  • 4-desmethoxy OMZ
  • Esomeprazol Magnesium Impurity B
  • Omeprazole EP Impurity B
Molecular Formula
C16H17N3O2S
Formula Weight
315.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
302 nm
SMILES
COC1=CC=C2C(N=C(S(CC3=C(C)C=C(C)C=N3)=O)N2)=C1
InChi Code
InChI=1S/C16H17N3O2S/c1-10-6-11(2)15(17-8-10)9-22(20)16-18-13-5-4-12(21-3)7-14(13)19-16/h4-8H,9H2,1-3H3,(H,18,19)
InChi Key
ZMXZYNHJPJEPAE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-desmethoxy Omeprazole is a potential impurity found in commercial omeprazole and esomeprazole magnesium preparations. Omeprazole (Item No. 14880) is a selective and irreversible inhibitor of the gastric H+/K+ ATPase pump (IC50 = 1.1 μM).1 It is a racemic mixture of two enantiomers, (S)-omeprazole (esomeprazole magnesium; Item No. 17326) and (R)-omeprazole (Item No. 18874), which are prodrugs of the active sulfonamide which is formed by acid-stimulated conversion.2,3 Both enantiomers are extensively metabolized by the cytochrome P450 (CYP) isomers CYP2C19 and CYP3A4.3

    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. Richardson, P., Hawkey, C.J., and Stack, W.A. Proton pump inhibitors. Pharmacology and rationale for use in gastrointestinal disorders. Drugs 56(3), 307-335 (1998).

    3. Shi, S., and Klotz, U. Proton pump inhibitors: An update of their clinical use and pharmacokinetics. Eur. J. Clin. Pharmacol. 64(10), 935-951 (2008).