Kontakt 2006, 8(1):146-148 | DOI: 10.32725/kont.2006.024
S-Zopiclone - a result of the "chiral rearrangement" strategyBiomedicine
- 1 Jihočeská univerzita v Českých Budějovicích, Zdravotně sociální fakulta, katedra radiologie a toxikologie
- 2 Lundbeck ČR, s.r.o., Praha
Zopiclone, derivative of cyclopyrrolone, is a hypnotic agent with short-term action. It belongs to a more recent, so called third generation of hypnotics, but its pharmacological profile is similar to that of benzodiazepines. Zopiclone has one chirality centre in its molecule and it exists in two stereoisomeric forms, but only one of them, S-zopiclone, is characterized by its hypnotic efficacy. The S-enantiomer of zopiclone was recently recommended for registration in the USA as a new medicine in the treatment of insomnia and thus, it is an example of a further psychopharmaceutical, in which the chiral rearrangement was recently shown to be useful.
Keywords: Zopiclone; hypnotic; chirality; S-zopiclone
Published: May 26, 2006 Show citation
References
- AGRANAT, I., CANER, H., CALDWELL, J.: Putting chirality to work: the strategy of chiral switches. Nat. Rev. Drug. Discov. 1: 753-768, 2002.
Go to original source...
Go to PubMed...
- ANONYM: Eszopiclone: esopiclone, Estorra, S-zopiclone, zopiclone-Sepracor.Drugs R.D. 6: 111-115, 2005.
Go to original source...
Go to PubMed...
- ANZENBACHER, P., JEZDINSKÝ, J.: Léčiva a chiralita. Klin. Farmak. Farmac. 17:148-150, 2003.
- BLASCHKE, G., HEMPEL, G., MULLER, W.E.: Preparative and analytical separation of the zopiclone enantiomers and determination of their affinity to the benzodiazepine receptor binding site. Chirality 5: 419-421, 1993.
Go to original source...
Go to PubMed...
- CARLSON, J.N., HASKEW, R., WACKER, J., ET AL.: Sedative and anxiolytic effects of zopiclone's enantiomers and metabolite. Eur. J. Pharmacol. 415: 181-189, 2001.
Go to original source...
Go to PubMed...
- DROVER, D.R.: Comparative pharmacokinetics and pharmacodynamics of short-acting hypnosedatives: zaleplon, zolpidem nad zopiclone. Clin. Pharmacokinet. 43: 227-238, 2004.
Go to original source...
Go to PubMed...
- FERNANDEZ, C., ALERT, P., DAVRINCHE, C., ET AL.: Stereoselective distribution and stereoconversion of zopiclone enantiomers in plasma and brain tissues in rats. J. Pharm. Pharmacol. 54: 335-340, 2002.
Go to original source...
Go to PubMed...
- FERNANDEZ, C., GIMENEZ, F., THUILLIER, A., ET AL.: Stereoselective binding of zopiclone to human plasma proteins. Chirality 11: 129-132, 1999.
Go to original source...
Go to PubMed...
- FERNANDEZ, C., MARTIN, C., GIMENEZ, F., ET AL.: Clinical pharmacokinetics of zopiclone. Clin. Pharmacokinet. 29: 431-441, 1995.
Go to original source...
Go to PubMed...
- GEORGIEV, V.: (S)-Zopiclone Sepracor. Curr. Opin Investic Drugs 2: 271-273, 2001.
- GLASS, J., LANCTOT, K.L., HERMANN, N., SPROULE, B.A., BUSTO, U.E.: Sedative hypnotics in older people with insomnia: meta-analysis of risks and benefits. BMJ. 2005; 331:1169. Epub 2005 Nov 11, 2005.
Go to original source...
Go to PubMed...
- KRYSTAL, A.D., WALSH, J.K., LASKA, E. ET AL.: Sustained efficacy of eszopiclone over 6 months of nightly treatment: results of a randomized, double-blind, placebo-controlled study in adults with chronic insomnia. Sleep 26: 793-799, 2003.
Go to original source...
Go to PubMed...
- NOBLE, S., LANGTRY, H.D., LAMB, H.M.: Zopiclone. An update of its pharmacology, clinical efficacy and tolerability in the treatment of insomnia. Drugs 55: 277-302, 1998.
Go to original source...
Go to PubMed...
- PATOČKA, J., DVOŘÁK, A.: Biomedical aspects of chiral molecules. J. Appl. Biomed. 2: 95-100, 2004a.
Go to original source...
- PATOČKA, J., DVOŘÁK, A.: Chirální léčiva v psychiatrii aneb psychofarmaka před a za zrcadlem. Psychiatrie 8: 27-30, 2004b.
- ROTH, T., WALSH, J.K., KRYSTAL, A., WESSEL, T., ROEHRS T.A.: An evaluation of the efficacy and safety of eszopiclone over 12 months in patiens with chronic primary insomnia. Slep Med. 6: 487-495, 2005.
Go to original source...
Go to PubMed...
- ŠVESTKA, J.: Escitalopram - selektivní stereoizomer citalopramu. Psychiatrie 7: 38-45, 2003.