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Cinazepam

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
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
  • 172986-25-3
PubChem CID
  • 629281
ChemSpider
  • 546502
UNII
  • U4SS7UFXC7
Chemical and physical data
FormulaC19H14BrClN2O5
Molar mass465.68 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 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 edit

References edit

  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.

cinazepam, sold, under, brand, name, levana, atypical, benzodiazepine, derivative, produces, pronounced, hypnotic, sedative, anxiolytic, effects, with, minimal, myorelaxant, side, effects, addition, unlike, many, other, benzodiazepine, nonbenzodiazepine, hypno. 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 CinazepamClinical dataATC codeNoneIdentifiersIUPAC name 4 7 Bromo 5 2 chlorophenyl 2 oxo 2 3 dihydro 1H 1 4 benzodiazepin 3 yl oxy 4 oxobutanoic acidCAS Number172986 25 3PubChem CID629281ChemSpider546502UNIIU4SS7UFXC7Chemical and physical dataFormulaC 19H 14Br Cl N 2O 5Molar mass465 68 g mol 13D model JSmol Interactive imageSMILES c1ccc c c1 C2 NC C O Nc3c2cc cc3 Br OC O CCC O O ClInChI 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 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 editGidazepam CloxazolamReferences edit 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 b cyclodextrin Pharmaceutical Chemistry Journal 32 10 513 515 doi 10 1007 BF02465736 ISSN 0091 150X S2CID 26513288 nbsp This sedative related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Cinazepam amp oldid 1194224126, wikipedia, wiki, book, books, library,

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