Cinazepam
Clinical data
ATC code
  • None
Identifiers
  • 4-{[7-Bromo-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-4-oxobutanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H14BrClN2O5
Molar mass465.68 g·mol−1
3D model (JSmol)
  • c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)OC(=O)CCC(=O)O)Cl
  • InChI=1S/C19H14BrClN2O5/c20-10-5-6-14-12(9-10)17(11-3-1-2-4-13(11)21)23-19(18(27)22-14)28-16(26)8-7-15(24)25/h1-6,9,19H,7-8H2,(H,22,27)(H,24,25)
  • Key:NQTRBZXDWMDXAQ-UHFFFAOYSA-N

Cinazepam (BD-798, sold under brand name Levana) is an atypical benzodiazepine derivative.[1] It produces pronounced hypnotic, sedative, and anxiolytic effects with minimal myorelaxant side effects.[2][3][4] In addition, unlike many other benzodiazepine and nonbenzodiazepine hypnotics such as diazepam, flunitrazepam, and zopiclone, cinazepam does not violate sleep architecture, and the continuity of slow-wave sleep and REM 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 of insomnia and other sleep disorders.[2]

Cinazepam has an order of magnitude lower affinity for the benzodiazepine receptor of the GABAA complex relative to other well-known hypnotic benzodiazepines such as nitrazepam and phenazepam.[2] Moreover, in mice, it is rapidly metabolized, with only 5% of the base compound remaining within 30 minutes of administration.[2] As such, cinazepam is considered to be a benzodiazepine prodrug; specifically, to 3-hydroxyphenazepam, as the main active metabolite.[2]

See also

References

  1. ^ Sleep Research. Vol. 26. Brain Information Service/Brain Research Institute, University of California. 1997. p. 115.
  2. ^ a b c d e f Schukin SI, Zinkovsky VG, Zhuk OV (2011). "Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice". Pharmacological Reports. 63 (5): 1093–1100. doi:10.1016/s1734-1140(11)70628-4. PMID 22180351. S2CID 4744087.
  3. ^ a b Makan SY, Boiko IA, Smul'skii SP, Andronati SA (2007). "Effect of cinazepam administration on the ligand affinity of neuromediator system receptors in rat brain". Pharmaceutical Chemistry Journal. 41 (5): 249–252. doi:10.1007/s11094-007-0055-9. ISSN 0091-150X. S2CID 24532012.
  4. ^ a b Andronati SA, Makan SY, Neshchadin DP, Yakubovskaya LN, Sava VM, Andronati KS (1998). "Bioaccessibility of cinazepam introduced as inclusion complex with β-cyclodextrin". Pharmaceutical Chemistry Journal. 32 (10): 513–515. doi:10.1007/BF02465736. ISSN 0091-150X. S2CID 26513288.
Categories