Eszopiclone: Treatment of Insomnia GABAergic Transmission Enhancer

Drugs of the Future

Volumn 28, Issue 7, 2003, Pages 640-646

  Culy, C ^a   Castaner J ^a   Bayes M ^a  

^a PROUS SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESZOPICLONE; HYPNOTIC AGENT; UNCLASSIFIED DRUG; ZOPICLONE;

ADULT; AGED; AREA UNDER THE CURVE; CHIRALITY; CHRONIC DISEASE; CLINICAL TRIAL; DRUG CLEARANCE; DRUG DEPENDENCE; DRUG EFFICACY; DRUG HALF LIFE; DRUG MECHANISM; DRUG TOLERABILITY; ENANTIOMER; GABAERGIC SYSTEM; GABAERGIC TRANSMISSION; HUMAN; INSOMNIA; LONG TERM CARE; NONHUMAN; REBOUND; REVIEW; SLEEP; TASTE DISORDER;

EID: 0142073864     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2003.028.07.743084     Document Type: Review

References (44)

1. Cotrel, C., Jeanmart, C., Messer, M.N. (Aventis Pharma SA). Pyrrolo(3,4-b)pyrazine derivs. DE 2300491, GB 1358680, JP 1977048687, US 3862149.
2. Gotor, V., Limeres, F., García, R., Bayod, M., Brieva, R. Enzymatic resolution of (±)-6-(5-chloropyridin-2-yl)-7- vinyloxy-carbonyloxy-6,7-dihydro[5H]pyrrolo[3, 4-b]pyrazin-5-one. Synthesis of (+)-zopiclone. Tetrahedron Asymmetry 1997, 8: 995-7.
3. Gotor Santamaría, V., Brieva Collado, R., Linares López, F.J., García Campos, R., Bayod Jasanada, M.S. (Asturpharma SA). (+)-6-(5-Chloropyrid-2-yl)-7-oxo-vinylcarbonyloxy-5,6-dihydropyrrolo[3,4b] pyrazine and their use in a process for the preparation of (+)-6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)-carbonyloxy-7-oxo-5, 6-dihydropyrrolo[3,4b]pyrazine. ES 2101653.
4. Solares, L.F., Díaz, M., Brieva, R., Sánchez, V.M., Bayod, M., Gotor, V. Enzymatic resolution of new carbonate intermediates for the synthesis of (S)-(+)-zopiclone. Tetrahedron Asymmetry 2002, 13: 2577-82.
5. Palomo, J.M., Mateo, C., Fernández-Lorente, G., Solares, L.F., Diaz, M., Sánchez, V.M., Bayod, M., Gotor, V., Guisan, J.M., Fernandez-Lafuente, R. Resolution of (± )-5-substituted-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine derivatives-precursors of (S)-(+)-zopiclone, catalyzed by immobilized Candida antarctica B lipase in aqueous media. Tetrahedron Asymmetry 2003, 14: 429-38.
6. Cotrel, C., Roussel, G. (Aventis Pharma SA). Optically active deriv. of 5H-pyrrolo[3,4-b]pyrazine, its preparation and pharmaceutical compsns. containing it. EP 0495717, EP 0609210, FR 2671800, JP 1994504548, US 6319926, US 6444673, WO 9212980.
7. 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 1993, 5: 419-21.
8. Mannaert, E., Daenens, P. Semi-preparative chiral resolution of zopiclone and N-desmethylzopiclone. J Pharm Biomed Anal 1996, 14: 1367-70.
9. Koppenhoefer, B., Jakob, A., Zhu, X., Lin, B. Separation of enantiomers of drugs by capillary electrophoresis with permethyl-γ-cyclodextrin as chiral solvating agent. HRC - J High Resolut Chromatogr 2000, 23: 413-29.
10. Schenck, C.H., Mahowald, M.W., Sack, R.L. Assessment and management of insomnia. JAMA - J Am Med Assoc 2003, 289: 2475-9.
11. Chesson, A.L. Jr., Anderson, W.M., Littner, M., Davila, D., Hartse, K., Johnson, S., Wise, M., Rafecas, J. Practice parameters for the nonpharmacologic treatment of chronic insomnia. An American Academy of Sleep Medicine report. Standards of Practice Committee of the American Academy of Sleep Medicine. Sleep 1999, 22: 1128-33.
12. Kupfer, D.J., Reynolds, C. F. Management of insomnia. New Engl J Med 1997, 336: 341-6.
13. National Sleep Foundation: 2003 Sleep in America Poll (March 2003). Available from URL: http:/www.findarticles.com/cf_dls/m3225/7_59/54591698/print.jhtml. Accessed July 22, 2003.
14. DSM-IV Diagnostic Criteria for Primary Insomnia. Available from: http://www.findarticles.com/cf_dls/m3225/7_59/54591698/print.jhtml. Accessed July 22, 2003
15. Wagner, J., Wagner, M.L. Nonbenzodiazepines for the treatment of insomnia. Sleep Med Rev 2000, 4: 551-81.
16. Moul, D.E., Nofzinger, E.A., Pilkonis, P.A., Houck, P.R., Miewald, J.M., Buysse, D.J. Symptom reports in severe chronic insomnia. Sleep 2002, 25: 553-63.
17. Ohayon, M.M., Roth, T. Place of chronic insomnia in the course of depressive and anxiety disorders. J Psychiatr Res 2003, 37: 9-15.
18. Spiegel, K., Leproult, R., Van Cauter, E. Impact of sleep debt on metabolic and endocrine function. Lancet. 1999, 354: 1435-9.
19. Martinez-Gonzalez, D., Obermeyer, W.H., Benca, R.M. Comorbidity of insomnia with medical and psychiatric disorders. Prim Psychiatry 2002, 9: 37-49.
20. Ayas, N.T., White, D.P., Manson, J.E., Stampfer, M.J., Speizer, F.E., Malhotra, A., Hu, F.B. A prospective study of sleep duration and coronary heart disease in women. Arch Intern Med 2003, 163: 205-9.
21. Walsh, J.K., Engelhardt, C.L. The direct economic costs of insomnia in the United States for 1995. Sleep 1999, 22(Suppl. 2): S386-93.
22. Terzano, M.G., Rossi, M., Palomba, V., Smerieri, A., Parrino, L. New drugs for insomnia: Comparative tolerability of zopiclone, zolpidem and zaleplon. Drug Saf 2003, 26: 261-82.
23. Noble, S., Langtry, H.D., Lamb, H.M. Zopiclone: An update of its pharmacology, clinical efficacy and tolerability in the treatment of insomnia. Drugs 1998, 55: 277-302.
24. Doble, A. New insights into the mechanism of action of hypnotics. J Psychopharmacol 1999, 13(4, Suppl. 1): S11-20.
25. Carlson, J.N., Haskew, R., Wacker, J., Maisonneuve, I.M., Glick, S.D., Jerussi, T.P. Sedative and anxiolytic effects of zopiclone's enantiomers and metabolite. Eur J Pharmacol 2001, 415: 181-9.
26. McMahon, L.R., Jerussi, T.P., France, C.P. Stereoselective discriminative stimulus effects of zopiclone in rhesus monkeys. Psychopharmacology 2003, 165: 222-8.
27. Fernandez, C., Gimenez, F., Baune, B., Maradeix, V., Thuillier, A. Determination of the enantiomers of zopiclone and its two chiral metabolites in urine using an automated coupled achiral-chiral chromatographic system. J Chromatogr - Biomed Appl 1993, 617(2): 271-8.
28. Fernandez, C., Baune, B., Gimenez, F., Thuillier, A., Farinotti, R. Determination of zopiclone enantiomers in plasma by liquid chromatography using a chiral cellulose carbamate column. J Chromatogr 1991, 572: 195-202.
29. Foster, R.T., Caillé, G., Ngoc, A.H., Lemko, C.H., Kherani, R., Pasutto, F.M. Stereospecific high-performance liquid chromatographic assay of zopiclone in human plasma. J Chromatogr - Biomed Appl 1994, 658: 161-6.
30. Hempel, G., Blaschke, G. Enantioselective determination of zopiclone and its metabolites in urine by capillary electrophoresis. J Chromatogr - Biomed Appl 1996, 675: 139-46.
31. Mannaert, E., Tytgat, J., Daenens, P. Development of a stereospecific radioimmunoassay for the analysis of zopiclone and metabolites in urine. Clin Chim Acta 1996, 253: 103-15.
32. Fernandez, C., Maradeix, V., Gimenez, F., Thuillier, A., Farinotti, R. Pharmacokinetics of zopiclone and its enantiomers in Caucasian young healthy volunteers. Drug Metab Dispos 1993, 21: 1125-8.
33. Foster, R.T., Caillé, G., Ngoc, A.H., Lemko, C.H., Kherani, R., Pasutto, F.M. Pharmacokinetics (PK) of zopiclone (ZPC) enantiomers in humans following oral dose administration of race-mate. Pharm Res 1994, 11 (10, Suppl.): Abst PPDM 8277.
34. Fernandez, C., Gimenez, F., Thuillier, A., Farinotti, R. Stereoselective binding of zopiclone to human plasma proteins. Chirality 1999, 11: 129-32.
35. Lamb, M., Maier, G., Caron, J., Powchik, P., Amato, D., Akylbekova, M., Russell, T. A daytime, double-blind, randomized, placebo-controlled, single dose-rising safety and pharmacokinetic study of (S)-zopiclone in healthy volunteers. Annu Meet Am Assoc Pharm Sci (AAPS) (Oct 29-Nov 2, Indianapolis) 2000, Abst 2090.
36. Fernandez, C., Alet, P., Cavrinche, C., Adrien, J., Thuillier, A., Farinotti, R., Gimenez, F. Stereoselective distribution and stereoconversion of zopiclone enantiomers in plasma and brain tissues in rats. J Pharm Pharmacol 2002, 54: 335-40.
37. Zammit, G.K., Gillin, J.C., McNabb, L., Caron, J., Roth, T. Eszopiclone, a novel non-benzodiazepine anti-insomnia agent: A six-week efficacy and safety study in adult patients with chronic insomnia. Sleep 2003, 26(Suppl.): Abst 0747.L.
38. Estorra™ six-week phase III study presented at Associated Professional Sleep Societies Meeting. Sepracor Press Release June 9, 2003.
39. Krystal, A.D., Walsh, J.K., Roth, T., Amato, D.A., Wessel, T. Six-month placebo-controlled efficacy of eszopiclone in chronic insomnia. 156th Annu Meet Am Psychiatr Assoc (May 17-22, San Francisco) 2003, Abst NR445.
40. Krystal, A., Walsh, J., Roth, T., Amato, D.A., Wessel, T. The sustained efficacy and safety of eszopiclone over six months of nightly treatment: A placebo-controlled study in patients with chronic insomnia. Sleep 2003, 26(Suppl.): Abst 0779.L.
41. Estorra™ one-year data presented at Associated Professional Sleep Societies Meeting. Sepracor Press Release June 9, 2003.
42. Tsutsui, S. A double-blind comparative study of zolpidem versus zopiclone in the treatment of chronic primary insomnia. J Int Med Res 2001, 29: 163-77.
43. Marketing clearance sought for Estorra for insomnia. DailyDrugNews.com (Daily Essentials) February 4, 2003.
44. Sepracor's Estorra moves into formal review. DailyDrugNews.com (Daily Essentials) April 4, 2003.