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    Zopiclone

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 43200-80-2, Imovane, Zimovane, Amoban, (+-)-zopiclone, Zopiclona
    Molecular Formula
    C17H17ClN6O3
    Molecular Weight
    388.8  g/mol
    InChI Key
    GBBSUAFBMRNDJC-UHFFFAOYSA-N
    FDA UNII
    03A5ORL08Q
    Zopiclone is the racemic form of a nonbenzodiazepine, cyclopyrrolone with hypnotic and sedative activity and without significant anxiolytic activity. Although the exact mechanism of action remains to be fully elucidated, zopiclone is able to bind to and activate the omega-1 subtype of the alpha subunit of the gamma-aminobutyric acid-benzodiazepine GABA receptor complex (GABA-A), a chloride ionophore complex in the central nervous system (CNS). This leads to the opening of chloride channels, causing hyperpolarization, inhibition of neuronal firing, and enhancement of the inhibitory effect of GABA. This eventually leads to a hypnotic effect and allows for an induction of sleep.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
    2.1.2 InChI
    InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3
    2.1.3 InChI Key
    GBBSUAFBMRNDJC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    03A5ORL08Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-(5-chloro-2-pyridyl)-6,7-dihydro- 7-oxo-5h-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1- Piperazinecarboxylate

    2. Imovane

    3. Limovan

    4. Nu-zopiclone

    5. Optidorm

    6. Ratio-zopiclone

    7. Rhovane

    8. Rp 27 267

    9. Siaten

    10. Somnosan

    11. Ximovan

    12. Zileze

    13. Zimoclone

    14. Zimovane

    15. Zop

    16. Zopi-puren

    17. Zopicalm

    18. Zopicalma

    19. Zopiclodura

    20. Zopiclon Abz

    21. Zopiclon Al

    22. Zopiclon Azu

    23. Zopiclon Beta

    24. Zopiclon Stada

    25. Zopiclon Tad

    26. Zopiclon Von Ct

    27. Zopiclon-neuraxpharm

    28. Zopiclon-ratiopharm

    29. Zopiclon-teva

    30. Zopitan

    31. Zorclone

    2.3.2 Depositor-Supplied Synonyms

    1. 43200-80-2

    2. Imovane

    3. Zimovane

    4. Amoban

    5. (+-)-zopiclone

    6. Zopiclona

    7. Zopiclonum

    8. Zopiclonum [inn-latin]

    9. Zopiclona [inn-spanish]

    10. Rp-27267

    11. [6-(5-chloropyridin-2-yl)-5-oxo-7h-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate

    12. Rp 27267

    13. 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

    14. Chebi:32315

    15. Amovane

    16. Nsc-758463

    17. Mls000083579

    18. 03a5orl08q

    19. 1-piperazinecarboxylic Acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo(3,4-b)pyrazin-5-yl Ester

    20. 1-piperazinecarboxylic Acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo[3,4-b]pyrazin-5-yl Ester

    21. 6-(5-chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate

    22. Ximovan

    23. 4-methyl-1-piperazinecarboxylic Acid Ester With 6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5h-pyrrolo(3,4-b)pyrazin-5-one

    24. Zopiclone (1.0 Mg/ml In Acetonitrile)

    25. Smr000048685

    26. Zopiclone [ban:inn:jan]

    27. 6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)carbonyloxy-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine

    28. Zopiclone (tn)

    29. Amoban (tn)

    30. Zopiclone (jan/inn)

    31. Sr-01000000090

    32. Einecs 256-138-9

    33. Dea No. 2784

    34. Brn 0768704

    35. Unii-03a5orl08q

    36. Zopiclone [inn:ban:jan]

    37. S-zopiclone

    38. Zimovane Ls

    39. 6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)carbonyloxy-7-oxo-6,7-dihydro-5h-pyrrolo(3,4-b)pyrazine

    40. Mfcd00133931

    41. (+/-)-zopiclone

    42. Zileze 7.5

    43. Zileze 3.75

    44. Zopiclone [inn]

    45. Zopiclone [jan]

    46. Zopiclone [mi]

    47. Opera_id_1759

    48. 27267 R.p.

    49. Biomol-nt_000284

    50. Zopiclone [mart.]

    51. Z 4900

    52. Zopiclone [who-dd]

    53. Lopac0_001270

    54. Schembl44419

    55. Mls000028547

    56. Mls001201837

    57. Mls001304058

    58. Bpbio1_001146

    59. Chembl135400

    60. Gtpl7430

    61. Zopiclone [ep Impurity]

    62. Dtxsid4041155

    63. Zopiclone [ep Monograph]

    64. Hms3267i08

    65. Hms3713h22

    66. Hms3746i05

    67. Pharmakon1600-01503425

    68. Bcp28513

    69. Hy-b0741

    70. Bbl010797

    71. Bdbm50248251

    72. Nsc758463

    73. Stk599439

    74. Zopiclone 1.0 Mg/ml In Acetonitrile

    75. Akos005520380

    76. Bcp9000663

    77. Ccg-205343

    78. Db01198

    79. Nsc 758463

    80. Ncgc00016108-04

    81. Ncgc00016108-05

    82. Ncgc00016108-06

    83. Ncgc00024993-03

    84. Ncgc00024993-04

    85. Vs-02685

    86. Sbi-0051236.p002

    87. Eu-0101270

    88. D01372

    89. 200z802

    90. Q220426

    91. Sr-01000000090-2

    92. Sr-01000000090-4

    93. Sr-01000000090-6

    94. Sr-01000000090-7

    95. W-106239

    96. Brd-a34309505-001-08-5

    97. Brd-a34309505-001-10-1

    98. Zopiclone, British Pharmacopoeia (bp) Reference Standard

    99. Zopiclone, European Pharmacopoeia (ep) Reference Standard

    100. (rs)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine-5-yl 4-methylpiperazine-1-carboxylate

    101. 1169825-88-0

    102. 4-methyl-1-piperazinecarboxylic Acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo(3,4-b)pyrazin-5-yl Ester

    103. 4-methyl-1-piperazinecarboxylic Acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo[3,4-b] Pyrazin-5-yl Ester

    104. 4-methyl-piperazine-1-carboxylic Acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl Ester

    105. 6-(5-chloropyridin-2-yl)-7-oxo-5h,6h,7h-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 388.8 g/mol
    Molecular Formula C17H17ClN6O3
    XLogP30.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass388.1050661 g/mol
    Monoisotopic Mass388.1050661 g/mol
    Topological Polar Surface Area91.8 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity573
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the short-term treatment of insomnia.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Zopiclone is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class and is indicated for the short-term treatment of insomnia. While Zopiclone is a hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties, it interacts with the gamma-aminobutyric acid-benzodiazepine (GABABZ) receptor complex. Subunit modulation of the GABABZ receptor chloride channel macromolecular complex is hypothesized to be responsible for some of the pharmacological properties of benzodiazepines, which include sedative, anxiolytic, muscle relaxant, and anticonvulsive effects in animal models. Zopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.

    5.2 MeSH Pharmacological Classification

    Hypnotics and Sedatives

    Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

    5.3 ATC Code

    N05CF01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N05 - Psycholeptics

    N05C - Hypnotics and sedatives

    N05CF - Benzodiazepine related drugs

    N05CF01 - Zopiclone

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following oral administration.

    5.5 Metabolism/Metabolites

    Extensively metabolized in the liver via decarboxylation (major pathway), demethylation, and side chain oxidation. Metabolites include an N-oxide derivative (weakly active; approximately 12% of a dose) and an N-desmethyl metabolite (inactive; approximately 16%). Approximately 50% of a dose is converted to other inactive metabolites via decarboxylation. Hepatic microsomal enzymes are apparently not involved in zopiclone clearance.

    5.6 Biological Half-Life

    Elimination half life is approximately 5 hours (range 3.8 to 6.5 hours) and is prolonged to 11.9 hours in patients with hepatic insufficiency.

    5.7 Mechanism of Action

    Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABABZ receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on 1, 2, 3 and 5 GABAA containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone.