(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
[CAS# 201856-53-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.39
• CAS Registry Number: 201856-53-3
• EC Number: 682-745-7
• SMILES: CCOC(C)O[C@@H]1[C@@H](N(C1=O)C(=O)C2=CC=CC=C2)C3=CC=CC=C3

Properties

• Density: 1.22

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone, commonly known as oxcarbazepine, was discovered in the late 1980s during research into anticonvulsant medications. Developed as a structural analog of carbamazepine, a well-established antiepileptic drug, oxcarbazepine was synthesized to improve upon the efficacy and tolerability profile of its predecessor. Through systematic modifications to the chemical structure, scientists identified oxcarbazepine as a promising candidate with enhanced pharmacological properties.

The primary application of oxcarbazepine is in the treatment of epilepsy and seizure disorders. As an anticonvulsant medication, it works by stabilizing neuronal membranes and reducing the abnormal electrical activity that leads to seizures. Oxcarbazepine is indicated for both partial and generalized seizures, including focal seizures and tonic-clonic seizures.

Oxcarbazepine is also utilized in the management of bipolar disorder, a mood disorder characterized by episodes of mania and depression. As a mood stabilizer, it helps to regulate mood swings and reduce the frequency and severity of manic and depressive episodes. While not approved specifically for bipolar disorder in all regions, oxcarbazepine is often prescribed off-label as an adjunctive treatment alongside other mood-stabilizing medications or antidepressants.

In addition to its anticonvulsant and mood-stabilizing properties, oxcarbazepine is employed in the management of neuropathic pain conditions. Neuropathic pain arises from damage or dysfunction of the nervous system and is characterized by shooting or burning sensations, tingling, or numbness. Oxcarbazepine's ability to modulate neuronal excitability and inhibit abnormal pain signaling pathways makes it effective in relieving neuropathic pain associated with conditions such as diabetic neuropathy, trigeminal neuralgia, and postherpetic neuralgia.

Oxcarbazepine may be prescribed off-label for various other conditions, including anxiety disorders, borderline personality disorder, and alcohol withdrawal syndrome. Its antiepileptic and mood-stabilizing properties, coupled with a favorable side effect profile, make it a versatile medication for addressing neurological and psychiatric symptoms.

Oxcarbazepine is approved for use in pediatric patients with epilepsy, providing a treatment option for children and adolescents affected by seizures. Its safety and efficacy in pediatric populations have been demonstrated in clinical trials, and it is often considered a first-line treatment for pediatric epilepsy, particularly in cases where carbamazepine is contraindicated or not well-tolerated.

References

2018. Tezacaftor. Pharmaceutical Substances. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0240