eszopiclone Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
hypnotic tranquillizers 1068 138729-47-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • eszopiclone
  • esopiclone
  • lunesta
A pyridine, pyrazine, and piperazine derivative that is used as a HYPNOTIC AND SEDATIVE in the treatment of INSOMNIA.
  • Molecular weight: 388.81
  • Formula: C17H17ClN6O3
  • CLOGP: 1.25
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 0
  • TPSA: 91.76
  • ALOGS: -2.64
  • ROTB: 3

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Dec. 15, 2004 FDA SUNOVION PHARMS INC

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dysgeusia 3010.00 60.67 574 1955 14245 4622218
Insomnia 1463.67 60.67 394 2135 44951 4591512
Completed suicide 997.35 60.67 289 2240 42156 4594307
Drug ineffective 965.15 60.67 408 2121 185653 4450810
Middle insomnia 367.24 60.67 75 2454 2387 4634076
Somnolence 251.46 60.67 105 2424 43555 4592908
Parasomnia 237.77 60.67 36 2493 176 4636287
Suicide attempt 235.29 60.67 82 2447 20760 4615703
Initial insomnia 231.74 60.67 46 2483 1257 4635206
Toxicity to various agents 215.72 60.67 110 2419 71930 4564533
Nightmare 203.40 60.67 57 2472 7033 4629430
Overdose 186.15 60.67 85 2444 43474 4592989
Amnesia 185.69 60.67 61 2468 12860 4623603
Intentional overdose 179.63 60.67 68 2461 21698 4614765
Somnambulism 167.04 60.67 37 2492 1731 4634732
Paradoxical drug reaction 166.54 60.67 34 2495 1071 4635392
Respiratory arrest 155.84 60.67 54 2475 13366 4623097
Cardiac arrest 137.70 60.67 64 2465 33943 4602520
Cardio-respiratory arrest 104.76 60.67 45 2484 19777 4616686
Depression 90.19 60.67 54 2475 47679 4588784
Hallucination 86.44 60.67 38 2491 17630 4618833
Suicidal ideation 82.22 60.67 39 2490 21544 4614919
Abnormal dreams 78.43 60.67 25 2504 4758 4631705
Drug hypersensitivity 74.75 60.67 55 2474 68345 4568118
Delirium 74.13 60.67 31 2498 12721 4623742
Headache 70.57 60.67 68 2461 122305 4514158
Anxiety 69.74 60.67 46 2483 47965 4588498
Altered state of consciousness 69.57 60.67 26 2503 7945 4628518
Poisoning 61.45 60.67 22 2507 5952 4630511

Pharmacologic Action:

SourceCodeDescription
ATC N05CF04 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Benzodiazepine related drugs
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D006993 Hypnotics and Sedatives
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:35488 central nervous system depressant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Insomnia indication 193462001
Suicidal thoughts contraindication 6471006
Asthenia contraindication 13791008
Alcohol intoxication contraindication 25702006
Depressive disorder contraindication 35489007
Hepatic failure contraindication 59927004
Sleep automatism contraindication 247962006
Severe chronic obstructive pulmonary disease contraindication 313299006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.95 Basic
pKa2 2.26 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA A receptor alpha-3/beta-2/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA A receptor alpha-3/beta-2/gamma-3 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA-A receptor alpha-1/beta-2/gamma-3 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA A receptor alpha-5/beta-2/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA A receptor alpha-5/beta-2/gamma-3 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-4 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.99 CHEMBL CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-2 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.94 CHEMBL CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-1 Ion channel Ki 7.30 CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-3 Ion channel Ki 6.79 CHEMBL

External reference:

IDSource
D000069582 MESH_DESCRIPTOR_UI
4024906 VUID
N0000175354 NUI
C1436328 UMLSCUI
D02624 KEGG_DRUG
409421001 SNOMEDCT_US
409420000 SNOMEDCT_US
461016 RXNORM
19107 MMSL
d05421 MMSL
4024906 VANDF
008781 NDDF
216714 MMSL
CHEMBL1522 ChEMBL_ID
DB00402 DRUGBANK_ID
UZX80K71OE UNII
8258 INN_ID
CHEBI:53760 CHEBI
969472 PUBCHEM_CID
7429 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0054-0290 TABLET 1 mg ORAL ANDA 20 sections
eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0054-0291 TABLET 2 mg ORAL ANDA 20 sections
eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0054-0292 TABLET 3 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5537 TABLET, FILM COATED 1 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5538 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5539 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5270 TABLET, FILM COATED 1 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5271 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5272 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
Lunesta HUMAN PRESCRIPTION DRUG LABEL 1 21695-225 TABLET, COATED 2 mg ORAL NDA 15 sections
Lunesta HUMAN PRESCRIPTION DRUG LABEL 1 21695-226 TABLET, COATED 3 mg ORAL NDA 15 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 33342-299 TABLET, FILM COATED 1 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 33342-300 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 33342-301 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-320 TABLET, FILM COATED 1 mg ORAL ANDA 20 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-321 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-322 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43063-795 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-097 TABLET, FILM COATED 3 mg ORAL ANDA 19 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-101 TABLET, FILM COATED 2 mg ORAL ANDA 19 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-185 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-200 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-828 TABLET, FILM COATED 3 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-829 TABLET, FILM COATED 2 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-830 TABLET, FILM COATED 1 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 47335-586 TABLET, FILM COATED 1 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 47335-587 TABLET, FILM COATED 2 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 47335-588 TABLET, FILM COATED 3 mg ORAL ANDA 19 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 50090-2606 TABLET, FILM COATED 1 mg ORAL ANDA 19 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3514 TABLET, FILM COATED 3 mg ORAL ANDA 20 sections