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Chemistry

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Also known as: 138729-47-2, Lunesta, (s)-zopiclone, Estorra, Esopiclone, (+)-zopiclone
Molecular Formula
C17H17ClN6O3
Molecular Weight
388.8  g/mol
InChI Key
GBBSUAFBMRNDJC-INIZCTEOSA-N
FDA UNII
UZX80K71OE

Eszopiclone
A pyridine, pyrazine, and piperazine derivative that is used as a HYPNOTIC AND SEDATIVE in the treatment of INSOMNIA.
1 2D Structure

Eszopiclone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(7S)-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/t16-/m0/s1
2.1.3 InChI Key
GBBSUAFBMRNDJC-INIZCTEOSA-N
2.1.4 Canonical SMILES
CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
2.1.5 Isomeric SMILES
CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
2.2 Other Identifiers
2.2.1 UNII
UZX80K71OE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Estorra

2. Lunesta

2.3.2 Depositor-Supplied Synonyms

1. 138729-47-2

2. Lunesta

3. (s)-zopiclone

4. Estorra

5. Esopiclone

6. (+)-zopiclone

7. Eszopiclon

8. Eszopiclone Civ

9. Sep-190

10. Zopiclone S-form

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

12. Chebi:53760

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

14. Sep-225441

15. Uzx80k71oe

16. (5s)-6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)carbonyloxy-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine

17. 1-piperazinecarboxylic Acid, 4-methyl-, (5s)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo(3,4-b)pyrazin-5-yl Ester

18. Gsk-1755165

19. Ncgc00159515-02

20. Dsstox_cid_26086

21. Dsstox_rid_81327

22. Dsstox_gsid_46086

23. Eszopiclone [usan:inn]

24. (5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate

25. (5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

26. Lunivia

27. (s)-eszopiclone

28. Estorra (tn)

29. Lunesta (tn)

30. Cas-138729-47-2

31. Hsdb 7472

32. Sr-05000001914

33. Dea No. 2784

34. Unii-uzx80k71oe

35. Zopiclon

36. Eszopiclone [usan]

37. Ks-1055

38. Sep-0227018

39. Sep-0227108

40. (s)-(+)-zopiclone

41. Eszopiclone [inn]

42. Eszopiclone [jan]

43. Eszopiclone [hsdb]

44. Eszopiclone [vandf]

45. Eszopiclone ( S-zopiclone)

46. Chembl1522

47. Eszopiclone [mart.]

48. Schembl28657

49. Eszopiclone [who-dd]

50. Mls001165744

51. Eszopiclone (jan/usp/inn)

52. Spectrum1505188

53. Zopiclone S-form [mi]

54. Gtpl7429

55. Dtxsid8046086

56. Eszopiclone [orange Book]

57. Eszopiclone Civ [usp-rs]

58. Hms2864o09

59. Hms3259b17

60. Hms3264f04

61. Eszopiclone [usp Monograph]

62. Bcp04910

63. Tox21_111733

64. Bdbm50247998

65. Mfcd03700720

66. Zinc19632834

67. Akos015895596

68. Tox21_111733_1

69. Ac-5546

70. Ac-5547

71. Ccg-213172

72. Db00402

73. Nc00663

74. Ncgc00159515-03

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

76. [(7s)-6-(5-chloro-2-pyridyl)-5-oxo-7h-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate

77. Smr000550478

78. En300-52506

79. D02624

80. Ab00828423_06

81. 729e472

82. A807426

83. Q413184

84. Sr-05000001914-1

85. Sr-05000001914-2

86. Eszopiclone, (+)-zopiclone, (s)-zopiclone, Estorra (r)-isomer

87. (+)-(5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl-4-methylpiperazine-1-carboxylate

88. (s)-4-methylpiperazine-1-carboxylic Acid 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl Ester

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

90. 1-piperazinecarobxylic Acid,4-methyl-,(5s)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo[3,4-b]pyrazin-5-yl Ester

91. 1140433-81-3

2.4 Create Date
2005-07-09
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 Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameEszopiclone
PubMed HealthEszopiclone (By mouth)
Drug ClassesNonbarbiturate Hypnotic
Drug LabelLUNESTA (eszopiclone) is a nonbenzodiazepine hypnotic agent that is a pyrrolopyrazine derivative of the cyclopyrrolone class. The chemical name of eszopiclone is (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazin-5-yl 4-met...
Active IngredientEszopiclone
Dosage FormTablet
RouteOral
Strength2mg; 1mg; 3mg
Market StatusPrescription
CompanyMylan Pharms; Glenmark Generics; Teva; Lupin; Dr Reddys Labs; Orchid Hlthcare; Sun Pharma Global; Roxane

2 of 4  
Drug NameLunesta
PubMed HealthEszopiclone (By mouth)
Drug ClassesNonbarbiturate Hypnotic
Drug LabelLUNESTA (eszopiclone) is a nonbenzodiazepine hypnotic agent that is a pyrrolopyrazine derivative of the cyclopyrrolone class. The chemical name of eszopiclone is (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazin-5-yl 4-met...
Active IngredientEszopiclone
Dosage FormTablet
RouteOral
Strength1mg; 2mg; 3mg
Market StatusPrescription
CompanySunovion Pharms

3 of 4  
Drug NameEszopiclone
PubMed HealthEszopiclone (By mouth)
Drug ClassesNonbarbiturate Hypnotic
Drug LabelLUNESTA (eszopiclone) is a nonbenzodiazepine hypnotic agent that is a pyrrolopyrazine derivative of the cyclopyrrolone class. The chemical name of eszopiclone is (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazin-5-yl 4-met...
Active IngredientEszopiclone
Dosage FormTablet
RouteOral
Strength2mg; 1mg; 3mg
Market StatusPrescription
CompanyMylan Pharms; Glenmark Generics; Teva; Lupin; Dr Reddys Labs; Orchid Hlthcare; Sun Pharma Global; Roxane

4 of 4  
Drug NameLunesta
PubMed HealthEszopiclone (By mouth)
Drug ClassesNonbarbiturate Hypnotic
Drug LabelLUNESTA (eszopiclone) is a nonbenzodiazepine hypnotic agent that is a pyrrolopyrazine derivative of the cyclopyrrolone class. The chemical name of eszopiclone is (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazin-5-yl 4-met...
Active IngredientEszopiclone
Dosage FormTablet
RouteOral
Strength1mg; 2mg; 3mg
Market StatusPrescription
CompanySunovion Pharms

4.2 Therapeutic Uses

Hypnotics and Sedatives; Sedative-hypnotic

National Library of Medicine's Medical Subject Headings online file (MeSH, 2006)


Eszopiclone is indicated for the treatment of insomnia. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1411


Eszopiclone is a nonbenzodiazepine hypnotic with a chemical structure unrelated to pyrazolopyrimidines, imidazopyridines, benzodiazepines, barbiturates,or other drugs with hypnotic properties.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1411


4.3 Drug Warning

Since sleep disturbances may be a manifestation of a physical and/or psychiatric disorder, symptomatic treatment of insomnia should be initiated only after careful evaluation of the patient. The failure of insomnia to remit after 7-10 days of therapy may indicate the presence of an underlying psychiatric and/or medical condition requiring evaluation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


Sedative and hypnotic agents are associated with numerous abnormal thought and behavioral processes (e.g., decreased inhibition, agitation, bizarre behavior, hallucinations, depersonalization, depression, suicidal ideation); many are similar to manifestations of alcohol intoxication or effects associated with other CNS depressants. Studies demonstrate short-term amnesic effects with eszopiclone. As with other sedative and hypnotic agents, emergence of new psychiatric abnormalities during eszopiclone therapy requires evaluation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


Studies using relatively high eszopiclone dosages (e.g., 2-4 times the recommended hypnotic dosage) in individuals with a history of benzodiazepine abuse suggest that the abuse potential of eszopiclone is similar to that of benzodiazepines (e.g., diazepam); caution is advised in patients with a history of drug or alcohol dependence or abuse.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


Physical dependence results in the manifestation of withdrawal symptoms (e.g., anxiety) upon rapid dose decrease or abrupt discontinuance of many sedative and hypnotic drugs, including eszopiclone. Clinical trials of eszopiclone did not reveal evidence of a serious withdrawal syndrome; however, anxiety, abnormal dreams, nausea, and upset stomach were reported at an incidence of 2% or less after placebo substitution within 48 hours following the last dose of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


For more Drug Warnings (Complete) data for ESZOPICLONE (16 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

Considering the man's weakened physical condition, 90 mg could represent a minimum lethal zopiclone dose. /Steroisomer/

PMID:9068198 Meatherall RC et al; J Forensic Sci 42 (2): 340-3 (1997)


4.5 Drug Indication

Eszopiclone is indicated for the treatment of insomnia.


Treatment of insomnia


5 Pharmacology and Biochemistry
5.1 Pharmacology

Eszopiclone rapidly induces sleep and decreases sleep latency. It also aids in the maintenance of sleep, preventing frequent awakenings. This drug has shown anticonvulsant and muscle relaxant properties in animals but is used in humans for its sedating effects. Eszopiclone is a central nervous system depressant with various effects. These include changes in alertness and motor coordination and the risk of next morning impairment, increasing with the amount of eszopiclone administered. Exercise caution and advise against driving a motor vehicle or activities that require full mental alertness the next morning. Complex sleep behaviors may result from eszopiclone use. Eszopiclone should be discontinued in these cases. Avoid the use of alcohol and other CNS depressants when eszopiclone is administered. Advise patients to skip the eszopiclone dose if alcohol has been consumed before bed or during the evening. Use the smallest dose of eszopiclone as possible, especially in elderly patients, who may experience exaggerated drug effects. Though the potential for dependence and abuse with eszopiclone is lower than for other hypnotic drugs, this drug has been abused and is known to cause dependence.


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

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CF - Benzodiazepine related drugs

N05CF04 - Eszopiclone


5.4 Absorption, Distribution and Excretion

Absorption

Eszopiclone is rapidly absorbed and the peak concentration is reached within about 1 hour after oral administration. The mean AUC after a 3 mg dose of eszopiclone was 278 ng/mL h. The consumption of a high-fat has been shown to slow absorption. Steady-state concentrations of eszopiclone are reached within 24-48 hours.


Route of Elimination

Only about 10% of an eszopiclone dose is found excreted in the urine as the parent drug. As much as 75% of an orally administered dose of racemic zopiclone as is found to be excreted in the urine in the form of metabolites. Eszopiclone, the S-isomer of racemic zopiclone, would likely show the same excretion pattern.


Volume of Distribution

The volume of distribution of eszopiclone is estimated at 89.9L


Clearance

The mean clearance of eszopiclone in young, healthy volunteers was 184 mL/min in one pharmacokinetic study.


Eszopiclone is rapidly absorbed following oral administration. Peak plasma concentrations are achieved within approximately 1 hour after oral administration. Eszopiclone is weakly bound to plasma protein (52-59%). The large free fraction suggests that eszopiclone disposition should not be affected by drug-drug interactions caused by protein binding. The blood-to-plasma ratio for eszopiclone is less than one, indicating no selective uptake by red blood cells.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 3139


Onset of action may be reduced if taken with or immediately after a high-fat or heavy meal.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1411


Up to 75% of an oral dose of racemic zopiclone is excreted in the urine, primarily as metabolites. A similar excretion profile would be expected for eszopiclone, the S-isomer of racemic zopiclone. Less than 10% of the orally administered eszopiclone dose is excreted in the urine as parent drug.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 3139


It is not known whether eszopiclone is distributed into milk; however, racemic zopiclone is distributed into milk. Use in nursing women is not recommended.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


For more Absorption, Distribution and Excretion (Complete) data for ESZOPICLONE (7 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Following oral administration, eszopiclone is extensively biotransformed and the major metabolites are S-desmethylzopiclone and zopiclone-N-oxide, which are largely inactive.. The enzymes involved in the metabolism of eszopiclone are CYP3A (the primary metabolizing enzyme), CYP2C8, and CYP2E1. The N-oxide derivative shows weak pharmacological activity in animals. The N-desmethyl metabolite is pharmacologically active.


Extensively metabolized by CYP3A4 and CYP2E1 via oxidation and demethylation. The two primary metabolites are (S)-zopiclone-N-oxide (inactive) and (S)-N-demethylzopiclone which binds to GABA receptors with lower potency then eszopiclone.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1411


Eszopiclone has known human metabolites that include N-desmethyl-zopiclone and N-oxide-zopiclone.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

The half-life is 6.1 hours in healthy patients but is prolonged in various patients, including those with hepatic impairment, elderly patients, in addition to those taking CYP3A enzyme inhibiting drugs.


Eszopiclone has an intermediate duration of action (i.e., possesses a half-life of approximately 5-7 hours).

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


5.7 Mechanism of Action

The exact mechanism of action of eszopiclone is unknown at this time but is thought to occur via binding with the GABA receptor complexes at binding sites located near benzodiazepine receptors, possibly explaining its hypnotic and sedative effects. It has particular affinity for GABA-A (or GABAA) receptor subunits 1, 3 and 5. Eszopiclone increases GABA-A channel currents significantly. GABA-A channels are major inhibitory channels that cause CNS depression when their receptors are activated.


Eszopiclone, the S-enantiomer of zopiclone (not commercially available in the US), is a sedative and hypnotic agent that is structurally unrelated to benzadiazepines and other sedative and hypnotic agents that are commercially available in the US, including barbiturates, imidazopyridines (e.g., zolpidem), and pyrazolopyrimidines (e.g., zaleplon). Eszopiclone is pharmacologically similar to zaleplon and zolpidem; all of these agents have been shown to interact with the CNS gamma-aminobutyric acid (GABA) receptor complex at binding domains located close to or allosterically coupled to benzodiazepine receptors.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2501


The precise mechanism of action of eszopiclone as a hypnotic is unknown. Its pharmalogic effect is believed to result from its interaction with GABA-receptor complexes at binding domains located close to or allosterically coupled to benzodiazepine receptors.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1411


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29-Jan-2021
24-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - TABLET;ORAL - 1MG

USFDA APPLICATION NUMBER - 21476

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DOSAGE - TABLET;ORAL - 2MG

USFDA APPLICATION NUMBER - 21476

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DOSAGE - TABLET;ORAL - 3MG

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