Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H17ClN6O3 |
Molecular Weight | 388.808 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)C(=O)O[C@@H]2N(C(=O)C3=C2N=CC=N3)C4=CC=C(Cl)C=N4
InChI
InChIKey=GBBSUAFBMRNDJC-INIZCTEOSA-N
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
Molecular Formula | C17H17ClN6O3 |
Molecular Weight | 388.808 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00402Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/eszopiclone.html
Sources: http://www.drugbank.ca/drugs/DB00402
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/eszopiclone.html
Eszopiclone is a nonbenzodiazepine hypnotic, pyrrolopyrazine derivative of the cyclopyrrolone class and is indicated for the short-term treatment of insomnia. While Eszopiclone 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. Eszopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor. The mechanism of action of Eszopiclone is not completely understood. It is thought that Eszopiclone acts on the benzodiazepine receptors as an agonist and interacts with GABA-receptor complexes. Used for the treatment of insomnia.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624 |
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Target ID: CHEMBL1962 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624 |
50.1 nM [Ki] | ||
Target ID: CHEMBL4956 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624 |
114.0 nM [Ki] | ||
Target ID: CHEMBL2472 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624 |
102.0 nM [Ki] | ||
Target ID: CHEMBL3026 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624 |
162.0 nM [Ki] | ||
Target ID: CHEMBL5742 Sources: http://www.drugbank.ca/drugs/DB00402 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LUNESTA Approved UseLUNESTA is indicated for the treatment of insomnia. Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.15 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
19.88 ng/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
40.28 ng/mL |
6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
10.29 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
25.48 ng/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
54.68 ng/mL |
6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.58 ng/mL |
1 mg 1 times / day multiple, oral dose: 1 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
26.18 ng/mL |
3 mg 1 times / day multiple, oral dose: 3 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
59.63 ng/mL |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.76 ng × h/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
166.21 ng × h/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
338.26 ng × h/mL |
6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
62.96 ng × h/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
187.76 ng × h/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
379.04 ng × h/mL |
6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
66.05 ng × h/mL |
1 mg 1 times / day multiple, oral dose: 1 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
191.07 ng × h/mL |
3 mg 1 times / day multiple, oral dose: 3 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
409.31 ng × h/mL |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.7 h |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESZOPICLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
44.45% |
ESZOPICLONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0 |
yes | yes (co-administration study) Comment: Coadministration with ketoconazole resulted in a 2.2-fold increase in exposure to eszopiclone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/eszopiclone.html
Usual Adult Dose for Insomnia
Initial dose: 1 mg orally immediately before bedtime
Maintenance dose: 1 to 3 mg orally immediately before bedtime
Maximum dose: 3 mg orally immediately before bedtime
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19639750
10 uM Eszopiclone increased the mean amplitude of the IGV-induced outward current from 19.7 ± 3.9 pA to 47.1 ± 7.8 pA (n = 10) and increased duration from 396.5 ± 24.0 s to 568.8 ± 40.5 s in rat pedunculopontine neurons.
Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:13:33 GMT 2025
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Mon Mar 31 18:13:33 GMT 2025
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Record UNII |
UZX80K71OE
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29756
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WHO-VATC |
QN05CF04
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WHO-ATC |
N05CF04
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LIVERTOX |
NBK548047
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C515051
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461016
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NN-76
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C65545
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Eszopiclone
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1068
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1255850
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m11663
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969472
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7429
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100000092238
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138729-47-2
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UZX80K71OE
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CHEMBL1522
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DB00402
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SUB21373
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UZX80K71OE
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8258
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ESZOPICLONE
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7472
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53760
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DTXSID8046086
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM) |
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EXCRETED UNCHANGED |
URINE
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Binds to the GABA receptor with significantly lower potency than eszopiclone.
MAJOR
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE INACTIVE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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