7-Chloro-1,2,3,4-tetrahydrobenzo[b]azepin-5-one
[CAS# 160129-45-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 7-Chloro-1,2,3,4-tetrahydrobenzo[b]azepin-5-one
• Molecular Formula: C₁₀H₁₀ClNO
• Molecular Weight: 195.65
• CAS Registry Number: 160129-45-3
• EC Number: 690-079-3
• SMILES: C1CC(=O)C2=C(C=CC(=C2)Cl)NC1

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

7-Chloro-1,2,3,4-tetrahydrobenzo[b]azepin-5-one, also known as clozapine, was discovered in the 1950s during efforts to develop new antipsychotic medications. Initially synthesized as part of a series of compounds by Swiss pharmaceutical company Wander AG, clozapine emerged as a novel compound with promising antipsychotic properties. Its unique chemical structure, characterized by a tricyclic framework containing a benzene ring fused to a seven-membered azepine ring, distinguished it from existing antipsychotic drugs. However, its development was initially overshadowed by concerns about agranulocytosis, a serious side effect observed in some patients. Despite these challenges, clozapine's efficacy in treating refractory schizophrenia ultimately led to its reintroduction in the 1970s and subsequent approval by regulatory authorities.

Clozapine is considered a second-line treatment for schizophrenia, particularly in patients who have not responded to other antipsychotic medications. Its unique pharmacological profile, including high affinity for serotonin receptors and moderate affinity for dopamine receptors, allows it to effectively manage both positive and negative symptoms of schizophrenia. Studies have shown that clozapine may be associated with a lower risk of suicide in patients with schizophrenia compared to other antipsychotic drugs. Its ability to improve mood, reduce aggression, and enhance social functioning contributes to its efficacy in preventing suicidal behavior.

Clozapine may be used as an adjunctive therapy in the management of bipolar disorder, particularly in cases where standard mood stabilizers are ineffective or poorly tolerated. Its mood-stabilizing properties help control manic and depressive episodes, reducing the frequency and severity of mood swings. Clozapine has been shown to reduce the risk of relapse and recurrence of mood episodes in patients with bipolar disorder. By stabilizing mood and addressing psychotic symptoms, it helps maintain long-term stability and improve overall functioning.

Clozapine is sometimes used off-label for the treatment of psychosis in patients with Parkinson's disease. Its efficacy in controlling hallucinations, delusions, and other psychotic symptoms associated with Parkinson's psychosis makes it a valuable treatment option in this population, particularly when other medications have failed or caused intolerable side effects.

One of the most significant risks associated with clozapine therapy is agranulocytosis, a severe and potentially life-threatening condition characterized by a marked decrease in white blood cell count. Regular monitoring of complete blood counts is essential to detect and manage this adverse effect promptly. Clozapine treatment is also associated with metabolic side effects such as weight gain, dyslipidemia, and insulin resistance. Therefore, patients receiving clozapine should undergo regular monitoring of metabolic parameters, including body weight, lipid levels, and fasting blood glucose, to mitigate the risk of cardiovascular complications.