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 1514.14 53.54 290 1025 8169 2348601
Insomnia 735.72 53.54 199 1116 25588 2331182
Completed suicide 553.80 53.54 153 1162 20881 2335889
Drug ineffective 447.51 53.54 193 1122 101431 2255339
Middle insomnia 207.14 53.54 42 1273 1435 2355335
Toxicity to various agents 156.96 53.54 67 1248 32687 2324083
Somnolence 142.75 53.54 57 1258 23428 2333342
Amnesia 140.73 53.54 42 1273 7211 2349559
Cardiac arrest 121.98 53.54 45 1270 14885 2341885
Parasomnia 116.60 53.54 17 1298 69 2356701
Intentional overdose 114.56 53.54 40 1275 11281 2345489
Respiratory arrest 107.83 53.54 33 1282 6145 2350625
Nightmare 105.73 53.54 29 1286 3668 2353102
Overdose 102.62 53.54 43 1272 19864 2336906
Paradoxical drug reaction 93.84 53.54 18 1297 455 2356315
Somnambulism 93.77 53.54 20 1295 870 2355900
Suicide attempt 88.34 53.54 33 1282 11249 2345521
Cardio-respiratory arrest 87.42 53.54 31 1284 9115 2347655
Initial insomnia 79.90 53.54 17 1298 730 2356040
Depression 62.22 53.54 34 1281 28098 2328672
Suicidal ideation 57.16 53.54 24 1291 11063 2345707

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 629.51 59.82 129 677 4920 1741055
Completed suicide 426.82 59.82 118 688 16194 1729781
Insomnia 394.49 59.82 111 695 16165 1729810
Drug ineffective 285.77 59.82 123 683 63678 1682297
Middle insomnia 159.13 59.82 31 775 851 1745124
Suicide attempt 135.54 59.82 41 765 7340 1738635
Parasomnia 114.22 59.82 17 789 81 1745894
Initial insomnia 106.09 59.82 20 786 456 1745519
Somnolence 99.18 59.82 40 766 16699 1729276
Overdose 88.96 59.82 37 769 16664 1729311
Intentional overdose 69.31 59.82 25 781 7645 1738330
Toxicity to various agents 63.68 59.82 35 771 29106 1716869
Altered state of consciousness 62.14 59.82 19 787 3478 1742497

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