flunitrazepam Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
diazepam derivatives 1202 1622-62-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flunitrazepam
  • flunidazepam
  • fluridrazepam
  • flunipam
A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.
  • Molecular weight: 313.29
  • Formula: C16H12FN3O3
  • CLOGP: 1.78
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 0
  • TPSA: 78.49
  • ALOGS: -4.56
  • ROTB: 2

Drug dosage:

DoseUnitRoute
1 mg O
1 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % 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
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 25 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1976 YEAR INTRODUCED

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
Intentional overdose 136.60 24.75 83 4526 64861 46616592
Suicide attempt 130.48 24.75 76 4533 54960 46626493
Neuroleptic malignant syndrome 127.13 24.75 46 4563 11076 46670377
Altered state of consciousness 125.28 24.75 56 4553 23292 46658161
Overdose 122.35 24.75 92 4517 101887 46579566
Psychiatric symptom 80.34 24.75 26 4583 4471 46676982
Salivary hypersecretion 60.21 24.75 23 4586 6422 46675031
Hepatic function abnormal 59.71 24.75 39 4570 34382 46647071
Blood creatine phosphokinase increased 59.62 24.75 36 4573 27688 46653765
Extrapyramidal disorder 57.12 24.75 26 4583 11242 46670211
Parkinsonism 55.53 24.75 23 4586 7925 46673528
Delusion 51.05 24.75 24 4585 11164 46670289
Stevens-Johnson syndrome 49.43 24.75 30 4579 23267 46658186
Pneumonia aspiration 48.05 24.75 33 4576 31572 46649881
Carcinoid tumour of the stomach 47.75 24.75 9 4600 158 46681295
Hypothermia 46.13 24.75 23 4586 12160 46669293
Hypergastrinaemia 44.62 24.75 8 4601 105 46681348
Depressed level of consciousness 44.18 24.75 37 4572 47532 46633921
Toxicity to various agents 43.33 24.75 76 4533 211690 46469763
Rhabdomyolysis 41.85 24.75 34 4575 41875 46639578
Enterochromaffin cell hyperplasia 41.66 24.75 7 4602 61 46681392
White blood cell count increased 40.25 24.75 34 4575 44185 46637268
Electrocardiogram QT prolonged 39.76 24.75 36 4573 51289 46630164
Loss of consciousness 36.47 24.75 49 4560 108189 46573264
Lip erosion 33.72 24.75 9 4600 790 46680663
Drowning 33.62 24.75 8 4601 441 46681012
Water intoxication 33.41 24.75 8 4601 453 46681000
Neuroendocrine tumour 31.38 24.75 8 4601 587 46680866
Peritoneal perforation 30.90 24.75 6 4603 124 46681329
Pyrexia 30.27 24.75 89 4520 348713 46332740
Liver disorder 28.59 24.75 26 4583 37220 46644233
Electrocardiogram J wave abnormal 28.18 24.75 4 4605 9 46681444
Sudden death 27.54 24.75 15 4594 9489 46671964
Aspiration 27.50 24.75 15 4594 9516 46671937
Brain injury 27.46 24.75 13 4596 6137 46675316
Schizophrenia 26.16 24.75 14 4595 8554 46672899
Ileus paralytic 25.18 24.75 11 4598 4312 46677141
Pain 25.07 24.75 8 4601 476940 46204513
Respiratory depression 24.75 24.75 15 4594 11585 46669868

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
Neuroleptic malignant syndrome 192.58 21.50 80 5001 16215 29931182
Rhabdomyolysis 89.56 21.50 79 5002 63501 29883896
Water intoxication 89.30 21.50 20 5061 482 29946915
Hepatic function abnormal 88.47 21.50 66 5015 41879 29905518
Pneumonia aspiration 74.23 21.50 57 5024 37723 29909674
Altered state of consciousness 69.91 21.50 43 5038 19876 29927521
Salivary hypersecretion 59.67 21.50 28 5053 7538 29939859
Psychiatric symptom 58.87 21.50 22 5059 3357 29944040
Asphyxia 55.24 21.50 24 5057 5401 29941996
Blood creatine phosphokinase increased 52.89 21.50 50 5031 43798 29903599
Polydipsia 46.89 21.50 19 5062 3594 29943803
White blood cell count increased 41.76 21.50 42 5039 39631 29907766
Delusion 39.81 21.50 25 5056 11964 29935433
Overdose 37.68 21.50 58 5023 84279 29863118
Suicide attempt 37.07 21.50 38 5043 36659 29910738
Toxicity to various agents 35.85 21.50 87 4994 177096 29770301
Lymphocyte percentage increased 34.70 21.50 8 5073 220 29947177
Parkinsonism 34.23 21.50 19 5062 7250 29940147
Stupor 33.14 21.50 14 5067 2939 29944458
Sciatic nerve neuropathy 30.57 21.50 6 5075 74 29947323
Sciatic nerve injury 29.00 21.50 6 5075 98 29947299
Insomnia 27.00 21.50 53 5028 93283 29854114
Persecutory delusion 26.90 21.50 11 5070 2129 29945268
Liver disorder 26.83 21.50 29 5052 29693 29917704
Hallucination, auditory 26.59 21.50 18 5063 9771 29937626
Somnolence 25.67 21.50 53 5028 96710 29850687
Mania 25.26 21.50 17 5064 9137 29938260
Intentional overdose 23.57 21.50 32 5049 41449 29905948
Sudden death 23.25 21.50 20 5061 15472 29931925
Seizure 22.74 21.50 51 5030 98424 29848973
Delirium 22.56 21.50 31 5050 40600 29906797
Depressed level of consciousness 22.50 21.50 30 5051 38192 29909205
Neonatal asphyxia 22.13 21.50 6 5075 323 29947074

Pharmacologic Action:

SourceCodeDescription
ATC N05CD03 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Benzodiazepine derivatives
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018682 GABA Agents
MeSH PA D018757 GABA Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:91016 gabaa receptor agonists

Drug Use (View source of the data)

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.89 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
Gamma-aminobutyric acid receptor subunit alpha-3 Ion channel ALLOSTERIC MODULATOR Ki 7.80 IUPHAR IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-5 Ion channel ALLOSTERIC MODULATOR Ki 8.26 IUPHAR IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-1 Ion channel ALLOSTERIC MODULATOR Ki 8.28 IUPHAR IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-2 Ion channel ALLOSTERIC MODULATOR Ki 8.28 IUPHAR IUPHAR
GABA-A receptor alpha-2/beta-3/gamma-2 Ion channel Ki 8.70 WOMBAT-PK
GABA A receptor alpha-3/beta-2/gamma-2 Ion channel Ki 8.82 WOMBAT-PK
GABA-A receptor alpha-3/beta-3/gamma-2 Ion channel Ki 8.35 WOMBAT-PK
GABA A receptor alpha-3/beta-2/gamma-3 Ion channel Ki 7.50 WOMBAT-PK
GABA A receptor alpha-5/beta-2/gamma-2 Ion channel Ki 9 WOMBAT-PK
GABA A receptor alpha-5/beta-2/gamma-3 Ion channel Ki 8.42 WOMBAT-PK
GABA A receptor alpha-5/beta-3/gamma-3 Ion channel Ki 8.42 WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-3 Ion channel Ki 7.46 WOMBAT-PK
GABA-A receptor alpha-1/beta-3/gamma-2 Ion channel Ki 8.47 WOMBAT-PK
GABA-A receptor alpha-5/beta-3/gamma-2 Ion channel Ki 8.84 WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel Ki 8.70 WOMBAT-PK
GABA-A receptor; anion channel Ion channel IC50 8.82 CHEMBL

External reference:

IDSource
N0000166924 NUI
D01230 KEGG_DRUG
C0016296 UMLSCUI
CHEBI:31622 CHEBI
CHEMBL13280 ChEMBL_ID
DB01544 DRUGBANK_ID
D005445 MESH_DESCRIPTOR_UI
4193 IUPHAR_LIGAND_ID
2951 INN_ID
620X0222FQ UNII
3380 PUBCHEM_CID
4460 RXNORM
004091 NDDF
387573007 SNOMEDCT_US
96237009 SNOMEDCT_US

Pharmaceutical products:

None