From Wikipedia, the free encyclopedia
Benzodiazepine medication
Cinazepam
ATC code
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
Formula C 19 H 14 Br Cl N 2 O 5
Molar mass 465.68 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
^
Sleep Research . Vol. 26. Brain Information Service/Brain Research Institute, University of California. 1997. p. 115.
^
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 .
^
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 .
^
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 .
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