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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1522
CHEMBL1522
Compound Name ESZOPICLONE
ChEMBL Synonyms ESZOPICLONE | LUNESTA | (S)-ZOPICLONE
Max Phase 4 (Approved)
Trade Names LUNESTA | ESZOPICLONE
Molecular Formula C17H17ClN6O3

Additional synonyms for CHEMBL1522 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1CCN(CC1)C(=O)O[C@@H]2N(C(=O)c3nccnc23)c4ccc(Cl)cn4
Standard InChI InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13( ...
Download InChI
Standard InChI Key GBBSUAFBMRNDJC-INIZCTEOSA-N

Sources

  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1522

Molecule Features

CHEMBL1522 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
GABA-A receptor; anion channel positive allosteric modulator GABA-A receptor; anion channel FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Marijuana AbuseD002189EFO:0004218marijuana dependence1ClinicalTrials
Sleep Apnea, ObstructiveD020181EFO:0003918obstructive sleep apnea2ClinicalTrials
Sleep Initiation and Maintenance DisordersD007319EFO:0004698insomnia4ClinicalTrials
DailyMed

Clinical Data

ClinicalTrials.gov ESZOPICLONE
The Cochrane Collaboration ESZOPICLONE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1522. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4701 Histamine H1 receptor Rattus norvegicus 0.536
CHEMBL240 HERG Homo sapiens 0.229
CHEMBL5747 CREB-binding protein Homo sapiens 0.202

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
388.8 388.1051 1.57 2 91.76 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 0 0 9 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 6.7 2.71 2.63 2 27 0.77

Structural Alerts

There are 1 structural alerts for CHEMBL1522. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05C - HYPNOTICS AND SEDATIVES
N05CF - Benzodiazepine related drugs
N05CF04 - eszopiclone

ChemSpider ChemSpider:GBBSUAFBMRNDJC-INIZCTEOSA-N
DailyMed eszopiclone
PubChem SID: 144205286 SID: 170465445 SID: 29215492 SID: 49666409
Wikipedia Eszopiclone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1522



ACToR 138729-47-2
ChEBI 53760
ChemicalBook CB1468825
DrugBank DB00402
DrugCentral 1068
eMolecules 2728749
EPA CompTox Dashboard DTXSID8046086
FDA SRS UZX80K71OE
Guide to Pharmacology 7429
Human Metabolome Database HMDB0014546
Mcule MCULE-3167182309 MCULE-5099990703
NIH Clinical Collection SAM002548982
Nikkaji J573.434G
PharmGKB PA162630444
PubChem 969472
PubChem: Drugs of the Future 12015386
PubChem: Thomson Pharma 14927588
SureChEMBL SCHEMBL28657
ZINC ZINC000019632834

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/GBBSUAFBMRNDJC-INIZCTEOSA-N spacer
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