Quetiapine N-oxide-fumaric acid (2/1)

Area of Science:

• Crystallography
• Medicinal Chemistry
• Organic Chemistry

Background:

• Quetiapine is an atypical antipsychotic used to treat schizophrenia and bipolar disorder.
• Oxidation products of pharmaceuticals can exhibit altered pharmacological profiles or toxicity.
• Understanding the structure of drug metabolites is crucial for drug development and safety assessment.

Purpose of the Study:

• To determine the crystal structure of a specific oxidation product of quetiapine hemifumaric acid.
• To elucidate the molecular conformation and intermolecular interactions of this compound in the solid state.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed.
• The crystal structure was solved and refined to characterize the molecular geometry and packing.

Main Results:

• The title compound, 2-{2-[4-(dibenzo[b,f][1,4]thia-zepin-11-yl)piperazin-1-yl 1-oxide]eth-oxy}ethanol-fumaric acid (2/1), was structurally characterized.
• The dibenzo[b,f][1,4]thiazepin ring adopted a boat conformation, with benzene rings inclined at 72.0(2)°.
• The piperazine ring adopted a chair conformation, with the ethoxyethanol side chain in an equatorial orientation.
• The crystal structure features corrugated layers formed by O-H⋯O hydrogen bonds between the compound and fumaric acid.

Conclusions:

• The study provides detailed structural insights into a quetiapine oxidation product.
• The observed conformations and hydrogen bonding patterns are important for understanding the compound's solid-state properties.
• This structural information can contribute to the broader understanding of quetiapine metabolism and degradation pathways.