eszopiclone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.11 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Dec. 15, 2004 FDA SUNOVION PHARMS INC

FDA Adverse Event Reporting System (Female)

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 669.24 12.85 295 13315 40196 46632256
Insomnia 310.87 12.85 306 13304 164618 46507834
Completed suicide 146.84 12.85 196 13414 145724 46526728
Middle insomnia 94.56 12.85 49 13561 9466 46662986
Parasomnia 72.18 12.85 18 13592 397 46672055
Depression 55.19 12.85 140 13470 169964 46502488
Suicidal ideation 50.91 12.85 72 13538 56310 46616142
Anxiety 48.22 12.85 139 13471 181818 46490634
Nightmare 47.27 12.85 39 13571 16559 46655893
Somnambulism 41.77 12.85 23 13587 5014 46667438
Paradoxical drug reaction 38.11 12.85 17 13593 2359 46670093
Amnesia 37.32 12.85 53 13557 41578 46630874
Initial insomnia 33.30 12.85 19 13591 4433 46668019
Overdose 29.01 12.85 80 13530 101899 46570553
Suicide attempt 28.86 12.85 55 13555 54981 46617471
Respiratory arrest 28.77 12.85 42 13568 33774 46638678
Abnormal sleep-related event 28.49 12.85 10 13600 737 46671715
Abnormal dreams 24.87 12.85 22 13588 10257 46662195
Drug ineffective 21.99 12.85 297 13313 677541 45994911
Blastocystis infection 21.94 12.85 4 13606 17 46672435
Concussion 21.08 12.85 17 13593 6986 46665466
Somnolence 20.39 12.85 95 13515 156426 46516026
Drug interaction 18.67 12.85 19 13591 203075 46469377
Cardiac arrest 17.44 12.85 62 13548 90337 46582115
Rheumatoid arthritis 17.36 12.85 27 13583 240188 46432264
Hangover 16.81 12.85 8 13602 1287 46671165
Ventricular tachyarrhythmia 16.41 12.85 4 13606 80 46672372
Cardio-respiratory arrest 16.06 12.85 46 13564 59823 46612629
Drug intolerance 15.62 12.85 12 13598 147037 46525415
Treatment failure 15.50 12.85 4 13606 93083 46579369
Agitation 15.28 12.85 43 13567 55372 46617080
Hallucination 15.01 12.85 40 13570 49911 46622541
Tremor 14.91 12.85 70 13540 115569 46556883
Maternal exposure during pregnancy 14.28 12.85 6 13604 102543 46569909
Acute kidney injury 13.93 12.85 30 13580 235825 46436627
Electrocardiogram QRS complex prolonged 13.86 12.85 12 13598 5437 46667015
Intentional overdose 13.80 12.85 46 13564 64898 46607554
Product substitution issue 13.26 12.85 19 13591 15012 46657440

FDA Adverse Event Reporting System (Male)

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 292.67 14.57 134 6929 24667 29920748
Insomnia 190.86 14.57 165 6898 93171 29852244
Completed suicide 149.17 14.57 148 6915 99344 29846071
Parasomnia 82.16 14.57 18 7045 276 29945139
Middle insomnia 70.46 14.57 32 7031 5741 29939674
Initial insomnia 68.46 14.57 25 7038 2564 29942851
Suicide attempt 63.09 14.57 59 7004 36638 29908777
Drug ineffective 61.13 14.57 197 6866 340190 29605225
Altered state of consciousness 34.15 14.57 32 7031 19887 29925528
Suicidal ideation 32.03 14.57 41 7022 36073 29909342
Somnolence 29.22 14.57 68 6995 96695 29848720
Nightmare 27.92 14.57 23 7040 12053 29933362
Somnambulism 27.60 14.57 14 7049 3200 29942215
Overdose 24.07 14.57 58 7005 84279 29861136
Anxiety 19.70 14.57 56 7007 89815 29855600
Abnormal dreams 17.81 14.57 15 7048 8100 29937315
Gun shot wound 15.76 14.57 7 7056 1191 29944224
Intentional overdose 15.74 14.57 32 7031 41449 29903966

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:35488 cns depressants
CHEBI has role CHEBI:35717 sedatives

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
4024906 VUID
N0000175354 NUI
D02624 KEGG_DRUG
4024906 VANDF
C1436328 UMLSCUI
CHEBI:53760 CHEBI
ZPC PDB_CHEM_ID
CHEMBL1522 ChEMBL_ID
DB00402 DRUGBANK_ID
D000069582 MESH_DESCRIPTOR_UI
969472 PUBCHEM_CID
7429 IUPHAR_LIGAND_ID
8258 INN_ID
UZX80K71OE UNII
461016 RXNORM
19107 MMSL
216714 MMSL
64025 MMSL
d05421 MMSL
008781 NDDF
409420000 SNOMEDCT_US
409421001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5537 TABLET, FILM COATED 1 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5538 TABLET, FILM COATED 2 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0093-5539 TABLET, FILM COATED 3 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5270 TABLET, FILM COATED 1 mg ORAL ANDA 32 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5271 TABLET, FILM COATED 2 mg ORAL ANDA 32 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 0378-5272 TABLET, FILM COATED 3 mg ORAL ANDA 32 sections
Lunesta HUMAN PRESCRIPTION DRUG LABEL 1 21695-225 TABLET, COATED 2 mg ORAL NDA 30 sections
Lunesta HUMAN PRESCRIPTION DRUG LABEL 1 21695-226 TABLET, COATED 3 mg ORAL NDA 30 sections
Eszopiclone Human Prescription Drug Label 1 33342-299 TABLET, FILM COATED 1 mg ORAL ANDA 31 sections
Eszopiclone Human Prescription Drug Label 1 33342-300 TABLET, FILM COATED 2 mg ORAL ANDA 31 sections
Eszopiclone Human Prescription Drug Label 1 33342-301 TABLET, FILM COATED 3 mg ORAL ANDA 31 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-320 TABLET, FILM COATED 1 mg ORAL ANDA 29 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-321 TABLET, FILM COATED 2 mg ORAL ANDA 29 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 42043-322 TABLET, FILM COATED 3 mg ORAL ANDA 29 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43063-795 TABLET, FILM COATED 3 mg ORAL ANDA 30 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-097 TABLET, FILM COATED 3 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-101 TABLET, FILM COATED 2 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-185 TABLET, FILM COATED 3 mg ORAL ANDA 32 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 43353-200 TABLET, FILM COATED 2 mg ORAL ANDA 32 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-828 TABLET, FILM COATED 3 mg ORAL ANDA 30 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-829 TABLET, FILM COATED 2 mg ORAL ANDA 30 sections
ESZOPICLONE HUMAN PRESCRIPTION DRUG LABEL 1 45865-830 TABLET, FILM COATED 1 mg ORAL ANDA 30 sections
ESZOPICLONE Human Prescription Drug Label 1 47335-586 TABLET, FILM COATED 1 mg ORAL ANDA 30 sections
ESZOPICLONE Human Prescription Drug Label 1 47335-587 TABLET, FILM COATED 2 mg ORAL ANDA 30 sections
ESZOPICLONE Human Prescription Drug Label 1 47335-588 TABLET, FILM COATED 3 mg ORAL ANDA 30 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 50090-2606 TABLET, FILM COATED 1 mg ORAL ANDA 31 sections
ESZOPICLONE Human Prescription Drug Label 1 50090-3514 TABLET, FILM COATED 3 mg ORAL ANDA 31 sections
ESZOPICLONE Human Prescription Drug Label 1 50090-3553 TABLET, FILM COATED 1 mg ORAL ANDA 31 sections
Eszopiclone HUMAN PRESCRIPTION DRUG LABEL 1 50090-3989 TABLET, FILM COATED 1 mg ORAL ANDA 30 sections
ESZOPICLONE Human Prescription Drug Label 1 50090-4202 TABLET, FILM COATED 2 mg ORAL ANDA 31 sections