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

Stem definitionDrug idCAS RN
hypnotic tranquillizers 2873 43200-80-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zopiclone
  • zimovane
  • imovane
S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007
  • 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:

DoseUnitRoute
7.50 mg O

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
Toxicity to various agents 2467.62 41.13 744 3773 71296 4563179
Coma 2020.17 41.13 476 4041 17043 4617432
Somnolence 1398.64 41.13 432 4085 43228 4591247
Intentional overdose 1293.19 41.13 349 4168 21417 4613058
Fall 1042.89 41.13 402 4115 77644 4556831
Overdose 859.96 41.13 300 4217 43259 4591216
Suicide attempt 847.31 41.13 249 4268 20593 4613882
Pneumonia aspiration 822.27 41.13 207 4310 9499 4624976
Confusional state 803.90 41.13 294 4223 48540 4585935
Poisoning deliberate 596.14 41.13 122 4395 2140 4632335
Drug dependence 541.89 41.13 139 4378 6828 4627647
Drug abuse 490.48 41.13 177 4340 27770 4606705
Hypotension 488.33 41.13 226 4291 67174 4567301
Electrocardiogram QT prolonged 429.70 41.13 138 4379 15157 4619318
Prescription form tampering 349.33 41.13 58 4459 284 4634191
Completed suicide 346.44 41.13 155 4362 42290 4592185
Intentional self-injury 328.62 41.13 95 4422 7288 4627187
Gastrooesophageal reflux disease 324.48 41.13 111 4406 14782 4619693
Depressed level of consciousness 303.21 41.13 106 4411 15048 4619427
Altered state of consciousness 273.91 41.13 84 4433 7887 4626588
Tachycardia 270.71 41.13 119 4398 31026 4603449
Acute kidney injury 269.37 41.13 154 4363 70277 4564198
Hepatocellular injury 253.48 41.13 79 4438 7821 4626654
Agitation 228.20 41.13 98 4419 24102 4610373
Bradycardia 228.07 41.13 96 4421 22473 4612002
Rhabdomyolysis 210.37 41.13 87 4430 19471 4615004
Loss of consciousness 206.56 41.13 103 4414 35579 4598896
Cholestasis 199.84 41.13 66 4451 7854 4626621
Hypothermia 198.17 41.13 57 4460 4277 4630198
Orthostatic hypotension 192.52 41.13 62 4455 6812 4627663
Intentional product misuse 174.57 41.13 75 4442 18418 4616057
Drug interaction 166.70 41.13 110 4407 64398 4570077
Hypoglycaemia 161.80 41.13 71 4446 18338 4616137
Miosis 154.68 41.13 43 4474 2847 4631628
Depression 152.17 41.13 93 4424 47640 4586835
Hyperkalaemia 148.68 41.13 64 4453 15773 4618702
Bradypnoea 145.72 41.13 32 4485 788 4633687
Malaise 144.32 41.13 115 4402 90042 4544433
Dysarthria 143.20 41.13 58 4459 12274 4622201
Foetal exposure during pregnancy 143.17 41.13 70 4447 23099 4611376
Mydriasis 138.87 41.13 42 4475 3746 4630729
Alcohol poisoning 136.20 41.13 31 4486 902 4633573
Disturbance in attention 134.06 41.13 53 4464 10528 4623947
Balance disorder 130.94 41.13 59 4458 16197 4618278
Hypokalaemia 125.91 41.13 60 4457 18700 4615775
Insomnia 123.50 41.13 80 4437 45265 4589210
Metabolic acidosis 122.43 41.13 52 4465 12388 4622087
Suicidal ideation 117.93 41.13 60 4457 21523 4612952
Hallucination 117.01 41.13 56 4461 17612 4616863
Blood creatine phosphokinase increased 115.89 41.13 53 4464 15046 4619429
Drug reaction with eosinophilia and systemic symptoms 115.39 41.13 49 4468 11664 4622811
Delirium 114.63 41.13 50 4467 12702 4621773
Substance abuse 113.15 41.13 30 4487 1658 4632817
Hyponatraemia 113.02 41.13 61 4456 24669 4609806
Anxiety 112.16 41.13 77 4440 47934 4586541
Death 111.11 41.13 143 4374 198020 4436455
Somnambulism 107.07 41.13 29 4488 1739 4632736
Hypotonia 106.59 41.13 34 4483 3612 4630863
Disorientation 105.99 41.13 47 4470 12412 4622063
Lactic acidosis 98.17 41.13 44 4473 11912 4622563
Eczema 97.78 41.13 36 4481 5885 4628590
Drug level increased 95.68 41.13 36 4481 6250 4628225
Macrophages increased 95.48 41.13 14 4503 23 4634452
Hypersensitivity vasculitis 95.19 41.13 29 4488 2647 4631828
Withdrawal syndrome 94.98 41.13 36 4481 6378 4628097
Hallucination, visual 94.21 41.13 35 4482 5867 4628608
Lung disorder 93.58 41.13 43 4474 12328 4622147
Sinus tachycardia 92.34 41.13 35 4482 6199 4628276
Coma scale abnormal 91.46 41.13 25 4492 1551 4632924
Hepatitis 91.00 41.13 42 4475 12163 4622312
Fatigue 89.26 41.13 110 4407 145456 4489019
Rash maculo-papular 88.38 41.13 37 4480 8492 4625983
Foetal death 87.98 41.13 27 4490 2525 4631950
Respiratory depression 87.82 41.13 32 4485 5078 4629397
Asphyxia 87.07 41.13 26 4491 2216 4632259
Hyperhidrosis 86.85 41.13 55 4462 29862 4604613
Tremor 86.62 41.13 59 4458 36200 4598275
Sudden death 86.36 41.13 32 4485 5323 4629152
Neuroleptic malignant syndrome 84.16 41.13 32 4485 5715 4628760
Cardio-respiratory arrest 82.53 41.13 46 4471 19776 4614699
Respiratory distress 82.07 41.13 38 4479 11078 4623397
Exposure during pregnancy 79.57 41.13 54 4463 32917 4601558
Maternal exposure during pregnancy 77.59 41.13 42 4475 17051 4617424
Blood pressure decreased 75.77 41.13 42 4475 17858 4616617
Drug withdrawal syndrome neonatal 75.40 41.13 22 4495 1730 4632745
Cardiomegaly 73.91 41.13 28 4489 4949 4629526
Amnesia 73.67 41.13 37 4480 12884 4621591
Toxic skin eruption 73.67 41.13 27 4490 4353 4630122
Bezoar 73.35 41.13 16 4501 381 4634094
Blood ethanol increased 72.74 41.13 13 4504 104 4634371
Mental disorder 72.45 41.13 31 4486 7503 4626972
Neutrophil count increased 70.96 41.13 27 4490 4828 4629647
Seizure 69.48 41.13 59 4458 50178 4584297
Extrapyramidal disorder 68.63 41.13 27 4490 5279 4629196
Transaminases increased 68.31 41.13 32 4485 9574 4624901
Diarrhoea 66.65 41.13 97 4420 150088 4484387
Pulmonary oedema 65.72 41.13 36 4481 14950 4619525
Sedation 65.24 41.13 29 4488 7688 4626787
Circulatory collapse 64.99 41.13 29 4488 7756 4626719
Toxic epidermal necrolysis 64.60 41.13 27 4490 6165 4628310
Sputum discoloured 64.33 41.13 20 4497 1951 4632524
Lethargy 63.65 41.13 37 4480 17204 4617271
Agranulocytosis 62.75 41.13 28 4489 7489 4626986
Aggression 62.64 41.13 34 4483 13865 4620610
Epilepsy 62.45 41.13 30 4487 9488 4624987
Abdominal pain 62.34 41.13 60 4457 59964 4574511
Condition aggravated 62.02 41.13 59 4458 58112 4576363
Thrombocytopenia 61.87 41.13 54 4463 47619 4586856
Implant site extravasation 61.86 41.13 14 4503 396 4634079
Shock 61.23 41.13 29 4488 8887 4625588
Gamma-glutamyltransferase increased 60.57 41.13 31 4486 11223 4623252
Nystagmus 60.39 41.13 20 4497 2388 4632087
Implant site infection 60.35 41.13 15 4502 639 4633836
Cardiac arrest 59.84 41.13 46 4471 33961 4600514
Off label use 59.59 41.13 85 4432 129028 4505447
Dehydration 59.14 41.13 50 4467 42240 4592235
Poisoning 58.82 41.13 25 4492 5949 4628526
Fracture 58.59 41.13 23 4494 4470 4630005
Nausea 58.53 41.13 100 4417 177233 4457242
Panic attack 58.05 41.13 25 4492 6142 4628333
Dysphagia 57.28 41.13 40 4477 25491 4608984
Oxygen saturation decreased 56.66 41.13 32 4485 14089 4620386
Distributive shock 56.58 41.13 12 4505 249 4634226
Pruritus 56.28 41.13 62 4455 72510 4561965
Pyrexia 56.11 41.13 75 4442 107069 4527406
Ataxia 54.59 41.13 23 4494 5354 4629121
Analgesic drug level increased 54.56 41.13 13 4504 463 4634012
Dizziness 53.97 41.13 71 4446 99800 4534675
Acute respiratory distress syndrome 53.32 41.13 25 4492 7488 4626987
Urinary tract infection 52.95 41.13 47 4470 42343 4592132
Sleep disorder 51.99 41.13 28 4489 11235 4623240
Foetal growth restriction 51.37 41.13 18 4499 2548 4631927
Hallucination, auditory 51.33 41.13 21 4496 4540 4629935
Speech disorder 51.31 41.13 28 4489 11534 4622941
Vomiting 51.13 41.13 76 4441 119623 4514852
Antipsychotic drug level above therapeutic 50.56 41.13 12 4505 420 4634055
Muscle rigidity 50.55 41.13 20 4497 3967 4630508
Onychomycosis 50.23 41.13 14 4503 933 4633542
Akathisia 49.25 41.13 19 4498 3524 4630951
Septic shock 49.05 41.13 31 4486 16735 4617740
Blood alcohol increased 48.75 41.13 11 4506 307 4634168
Foetal alcohol syndrome 47.67 41.13 8 4509 42 4634433
Hypertension 47.54 41.13 48 4469 50750 4583725
Oedema peripheral 47.44 41.13 44 4473 41928 4592547
Electrocardiogram QRS complex prolonged 47.44 41.13 16 4501 2020 4632455
Drug diversion 47.05 41.13 12 4505 568 4633907
Urinary retention 46.91 41.13 25 4492 9822 4624653
Conjunctival hyperaemia 46.21 41.13 14 4503 1252 4633223
Faecaloma 45.94 41.13 15 4502 1713 4632762
Agitation neonatal 44.92 41.13 11 4506 440 4634035
Scratch 44.82 41.13 14 4503 1386 4633089
Femur fracture 44.43 41.13 23 4494 8516 4625959
Wound dehiscence 44.40 41.13 14 4503 1429 4633046
Rectal haemorrhage 44.34 41.13 26 4491 12270 4622205
Jaundice 44.00 41.13 26 4491 12448 4622027
Unresponsive to stimuli 43.56 41.13 24 4493 10069 4624406
Dextrocardia 43.25 41.13 8 4509 79 4634396
Hyperthermia 42.79 41.13 17 4500 3407 4631068
Accidental overdose 42.69 41.13 23 4494 9232 4625243
Hypertonia 42.39 41.13 16 4501 2796 4631679
Abnormal behaviour 42.18 41.13 25 4492 12031 4622444
Cyanosis 41.99 41.13 20 4497 6202 4628273
Inappropriate antidiuretic hormone secretion 41.50 41.13 18 4499 4496 4629979
Ischaemic stroke 41.19 41.13 21 4496 7533 4626942
Stress 41.13 41.13 23 4494 9925 4624550

Pharmacologic Action:

SourceCodeDescription
ATC N05CF01 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 central nervous system depressant
CHEBI has role CHEBI:35717 sedative

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-5/beta-3/gamma-2 Ion channel POSITIVE MODULATOR Ki 7.28 WOMBAT-PK DRUG LABEL
GABA A receptor alpha-3/beta-2/gamma-2 Ion channel POSITIVE MODULATOR Ki 6.58 WOMBAT-PK DRUG LABEL
GABA A receptor alpha-3/beta-2/gamma-3 Ion channel POSITIVE MODULATOR Ki 6.49 WOMBAT-PK DRUG LABEL
GABA-A receptor alpha-1/beta-2/gamma-3 Ion channel POSITIVE MODULATOR Ki 7.15 WOMBAT-PK DRUG LABEL
GABA A receptor alpha-5/beta-2/gamma-2 Ion channel POSITIVE MODULATOR Ki 7.28 WOMBAT-PK DRUG LABEL
GABA A receptor alpha-5/beta-2/gamma-3 Ion channel POSITIVE MODULATOR Ki 6.75 WOMBAT-PK DRUG LABEL
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel POSITIVE MODULATOR Ki 7.18 WOMBAT-PK DRUG LABEL
GABA A receptor alpha-5/beta-3/gamma-3 Ion channel POSITIVE MODULATOR Ki 6.75 WOMBAT-PK DRUG LABEL
GABA-A receptor; anion channel Ion channel IC50 7.54 CHEMBL

External reference:

IDSource
C0078847 UMLSCUI
D01372 KEGG_DRUG
03A5ORL08Q UNII
4462 INN_ID
321174005 SNOMEDCT_US
003775 NDDF
40001 RXNORM
395929002 SNOMEDCT_US
CHEMBL135400 ChEMBL_ID
DB01198 DRUGBANK_ID
CHEBI:32315 CHEBI
5735 PUBCHEM_CID
7430 IUPHAR_LIGAND_ID
C515050 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

None