Chemistry:Ro5-4864

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Short description: Chemical compound
Ro5-4864
Ro5-4864.svg
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Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H12Cl2N2O
Molar mass319.185 g·mol−1
3D model (JSmol)
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Ro5-4864[1] (4'-chlorodiazepam) is a drug which is a benzodiazepine derivative of diazepam.[2] However unlike most benzodiazepine derivatives, Ro5-4864 lacks affinity for GABAA receptors and lacks typical benzodiazepine effects,[3] instead being sedative yet also convulsant and anxiogenic in effects.[4][5][6][7] Ro5-4864 was found to be a potent ligand for the "peripheral benzodiazepine receptor",[8] later renamed to mitochondrial translocator protein 18kDa (TSPO). Despite its convulsant effects, at lower doses Ro5-4864 has proved to be neuroprotective and has become widely used for research into the role of the TSPO protein in neurotoxicity.[9][10][11][12][13][14] In vitro studies and rodent models also suggest the possibility of analgesic,[15] antidepressant,[16] cardioprotective,[17] and anti-cancer effects.[18][19][20][21][non-primary source needed]

See also

References

  1. ↑ Reeder E, Sternbach LH, "Amino substituted benzophenone oximes and derivatives thereof", US patent 3136815, issued 9 June 1964, assigned to F Hoffmann La Roche AG
  2. ↑ "Experimental versus theoretical log D7.4 , pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis 10 (8): 1258–1269. March 2018. doi:10.1002/dta.2387. PMID 29582576. https://rke.abertay.ac.uk/en/publications/527a634d-decc-4d3a-bdca-08659bb13ed6. 
  3. ↑ "Differential effects of GABA on peripheral and central type benzodiazepine binding sites in brain". Neuroscience Letters 30 (2): 157–160. May 1982. doi:10.1016/0304-3940(82)90289-0. PMID 6287365. 
  4. ↑ "Pharmacological, electrophysiological, and neurochemical actions of the convulsant benzodiazepine Ro 5-4864 (4'-chlordiazepam)". Advances in Biochemical Psychopharmacology 38: 139–151. 1983. PMID 6670623. 
  5. ↑ "The anxiogenic action of Ro 5-4864 is reversed by phenytoin". Neuroscience Letters 35 (1): 93–96. January 1983. doi:10.1016/0304-3940(83)90532-3. PMID 6682534. 
  6. ↑ "On the convulsant action of Ro 5-4864 and the existence of a micromolar benzodiazepine binding site in rat brain". Psychopharmacology 82 (3): 199–202. 1984. doi:10.1007/BF00427773. PMID 6326177. 
  7. ↑ "Behavioural actions of Ro 5-4864: a peripheral-type benzodiazepine?". Life Sciences 35 (3): 229–240. July 1984. doi:10.1016/0024-3205(84)90106-1. PMID 6087055. 
  8. ↑ "Characterization of peripheral-type benzodiazepine binding sites in brain using [3H]Ro 5-4864". Molecular Pharmacology 22 (1): 26–32. July 1982. PMID 6289073. 
  9. ↑ "Ro5-4864, a peripheral benzodiazepine receptor ligand, reduces reactive gliosis and protects hippocampal hilar neurons from kainic acid excitotoxicity". Journal of Neuroscience Research 80 (1): 129–137. April 2005. doi:10.1002/jnr.20430. PMID 15696538. 
  10. ↑ "Ro5-4864, a synthetic ligand of peripheral benzodiazepine receptor, reduces aging-associated myelin degeneration in the sciatic nerve of male rats". Mechanisms of Ageing and Development 126 (11): 1159–1163. November 2005. doi:10.1016/j.mad.2005.06.001. PMID 16045970. 
  11. ↑ "The peripheral-type benzodiazepine receptor is involved in control of Ca2+-induced permeability transition pore opening in rat brain mitochondria". Cell Calcium 42 (1): 27–39. July 2007. doi:10.1016/j.ceca.2006.11.004. PMID 17174393. 
  12. ↑ "Ro5-4864 promotes neonatal motor neuron survival and nerve regeneration in adult rats". The European Journal of Neuroscience 27 (4): 937–946. February 2008. doi:10.1111/j.1460-9568.2008.06065.x. PMID 18333964. 
  13. ↑ "Neuroprotective effect of Ro5-4864 following brain injury". Experimental Neurology 214 (2): 201–208. December 2008. doi:10.1016/j.expneurol.2008.08.008. PMID 18789929. 
  14. ↑ "Neuroprotective effects of a ligand of translocator protein-18 kDa (Ro5-4864) in experimental diabetic neuropathy". Neuroscience 164 (2): 520–529. December 2009. doi:10.1016/j.neuroscience.2009.08.005. PMID 19665520. 
  15. ↑ "Antinociceptive effects of peripheral benzodiazepine receptors". Pharmacology 70 (4): 188–194. April 2004. doi:10.1159/000075547. PMID 15001819. 
  16. ↑ "Antidepressant-like effect of Ro5-4864, a peripheral-type benzodiazepine receptor ligand, in forced swimming test". European Journal of Pharmacology 471 (1): 21–26. June 2003. doi:10.1016/S0014-2999(03)01789-8. PMID 12809948. 
  17. ↑ "Mitochondrial instability during regional ischemia-reperfusion underlies arrhythmias in monolayers of cardiomyocytes". Journal of Molecular and Cellular Cardiology 78: 90–99. January 2015. doi:10.1016/j.yjmcc.2014.09.024. PMID 25268650. 
  18. ↑ "Peripheral benzodiazepine receptor-induced myocardial protection is mediated by inhibition of mitochondrial membrane permeabilization". The Journal of Pharmacology and Experimental Therapeutics 323 (1): 336–345. October 2007. doi:10.1124/jpet.107.124255. PMID 17640950. 
  19. ↑ "Channel-like functions of the 18-kDa translocator protein (TSPO): regulation of apoptosis and steroidogenesis as part of the host-defense response". Current Pharmaceutical Design 13 (23): 2385–2405. 2007. doi:10.2174/138161207781368710. PMID 17692008. 
  20. ↑ "Translocator protein (18 kDa) TSPO: an emerging therapeutic target in neurotrauma". Experimental Neurology 219 (1): 53–57. September 2009. doi:10.1016/j.expneurol.2009.04.016. PMID 19409385. 
  21. ↑ "4'-Chlorodiazepam, a translocator protein (18 kDa) antagonist, improves cardiac functional recovery during postischemia reperfusion in rats". Experimental Biology and Medicine 235 (4): 478–486. April 2010. doi:10.1258/ebm.2009.009291. PMID 20407080. 



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