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Synopsis

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Chemistry

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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

Zopiclone

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 Formula	C₁₇H₁₇ClN₆O₃
Molecular Weight	388.8 g/mol
XLogP3	0.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	388.1050661 g/mol
Monoisotopic Mass	388.1050661 g/mol
Topological Polar Surface Area	91.8 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	573
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 (GABA_BZ) receptor complex. Subunit modulation of the GABA_BZ 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 GABA_BZ 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.

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