 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C19H14BrClN2O5 |
| Molar mass | 465.68 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Cinazepam (BD-798, sold under brand nameLevana) is an atypicalbenzodiazepine derivative.[1] It produces pronouncedhypnotic,sedative, andanxiolytic effects with minimalmyorelaxantside effects.[2][3][4] In addition, unlike many other benzodiazepine andnonbenzodiazepine hypnotics such asdiazepam,flunitrazepam, andzopiclone, cinazepam does not violatesleep architecture, and the continuity ofslow-wave sleep andREM sleep are proportionally increased.[2][3][4] As such, cinazepam produces a sleep state close to physiological, and for that reason, may be advantageous compared to other, related drugs in the treatment ofinsomnia and othersleep disorders.[2]
Cinazepam has an order of magnitude loweraffinity for thebenzodiazepine receptor of theGABAA complex relative to other well-known hypnotic benzodiazepines such asnitrazepam andphenazepam.[2] Moreover, in mice, it is rapidlymetabolized, with only 5% of the base compound remaining within 30 minutes of administration.[2] As such, cinazepam is considered to be a benzodiazepineprodrug; specifically, to3-hydroxyphenazepam, as the mainactive metabolite.[2]
The reaction between 2-amino-5-bromo-2'-chlorobenzophenone [60773-49-1] (1) and bromoacetyl bromide [598-21-0] gives 5-bromo-2'-chloro-2-bromoacetamido-benzophenone, PC33695403 (2). Finkelstein reaction with sodium iodide gives PC11375008 (3). Reaction with hydroxylamine preferentially causes alkylation by displacement of the leaving group than oxime formation. Hence, the product of this step is PC129780422 (4). Ring closure in acid led to Phenazepam 4-Oxide [1177751-52-8] (5). Treatment with acetic anhydride and Polonovski rearrangement gave PC630731 (6). Saponification of the ester yielded 3-Hydroxyphenazepam [70030-11-4] (7). Treatment with succinic anhydride completed the synthesis of Cinazepam (8).
