Omeprazole Sulfone: A Key Metabolite and Analytical Marker in Proton Pump Inhibitor Research
Omeprazole Sulfone is a primary oxidative metabolite of Omeprazole, a widely prescribed proton pump inhibitor (PPI) used to treat acid-related gastrointestinal conditions such as gastroesophageal reflux disease (GERD), gastric ulcers, and Zollinger-Ellison syndrome. While not active as a therapeutic agent itself, omeprazole sulfone plays a crucial role in pharmacokinetic studies, drug metabolism research, and quality control testing.
Chemical Overview
IUPAC Name: 5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole 1-oxide
Molecular Formula: C₁₇H₁₉N₃O₄S
Molecular Weight: 361.41 g/mol
CAS Number: 95510-70-6
Structure: Omeprazole sulfone is derived from omeprazole via oxidation at the sulfur atom, forming a sulfone (–SO₂–) functional group.
Formation and Role
Omeprazole sulfone is primarily formed in the liver by cytochrome P450 enzymes, particularly CYP3A4. This oxidative pathway is one of several that metabolize omeprazole, alongside hydroxylation and demethylation.
Key Points:
It is a major Phase I metabolite.
It is pharmacologically inactive, lacking proton pump inhibitory action.
Its concentration in plasma serves as a marker for metabolic rate and enzyme activity, particularly CYP3A4.