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 148.28 25.71 86 4759 67119 53277102
Suicide attempt 140.54 25.71 79 4766 58089 53286132
Neuroleptic malignant syndrome 131.10 25.71 47 4798 11986 53332235
Altered state of consciousness 129.66 25.71 57 4788 24779 53319442
Overdose 129.20 25.71 94 4751 107642 53236579
Psychiatric symptom 80 25.71 26 4819 4927 53339294
Hepatic function abnormal 72.82 25.71 44 4801 36855 53307366
Salivary hypersecretion 64.03 25.71 24 4821 6919 53337302
Extrapyramidal disorder 63.17 25.71 28 4817 12374 53331847
Blood creatine phosphokinase increased 60.91 25.71 36 4809 28949 53315272
Pneumonia aspiration 57.80 25.71 37 4808 34264 53309957
Parkinsonism 54.59 25.71 23 4822 8990 53335231
Stevens-Johnson syndrome 52.88 25.71 31 4814 24551 53319670
Toxicity to various agents 52.86 25.71 81 4764 219517 53124704
Delusion 51.34 25.71 24 4821 11985 53332236
Depressed level of consciousness 48.71 25.71 40 4805 54388 53289833
Carcinoid tumour of the stomach 48.50 25.71 9 4836 158 53344063
Hypothermia 46.43 25.71 23 4822 13033 53331188
Hypergastrinaemia 45.29 25.71 8 4837 105 53344116
Rhabdomyolysis 42.94 25.71 34 4811 43889 53300332
Loss of consciousness 42.38 25.71 52 4793 114160 53230061
Enterochromaffin cell hyperplasia 42.24 25.71 7 4838 61 53344160
White blood cell count increased 41.40 25.71 34 4811 46211 53298010
Electrocardiogram QT prolonged 41.39 25.71 37 4808 56366 53287855
Drowning 39.70 25.71 9 4836 436 53343785
Lip erosion 37.76 25.71 10 4835 927 53343294
Respiratory depression 35.27 25.71 19 4826 12787 53331434
Water intoxication 33.75 25.71 8 4837 472 53343749
Peritoneal perforation 31.40 25.71 6 4839 124 53344097
Neuroendocrine tumour 31.06 25.71 8 4837 665 53343556
Pain 30.46 25.71 8 4837 588390 52755831
Pyrexia 29.70 25.71 92 4753 403101 52941120
Liver disorder 28.77 25.71 26 4819 40129 53304092
Electrocardiogram J wave abnormal 28.52 25.71 4 4841 9 53344212
Brain injury 27.99 25.71 13 4832 6392 53337829
Aspiration 27.70 25.71 15 4830 10195 53334026
Sudden death 27.65 25.71 15 4830 10233 53333988

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 204.33 19.86 84 5171 17411 32490860
Rhabdomyolysis 91.00 19.86 80 5175 67185 32441086
Water intoxication 90.23 19.86 20 5235 483 32507788
Hepatic function abnormal 89.60 19.86 67 5188 44773 32463498
Pneumonia aspiration 78.89 19.86 60 5195 41096 32467175
Altered state of consciousness 72.94 19.86 45 5210 21952 32486319
Salivary hypersecretion 59.18 19.86 28 5227 8060 32500211
Asphyxia 58.93 19.86 25 5230 5575 32502696
Psychiatric symptom 54.96 19.86 21 5234 3573 32504698
Blood creatine phosphokinase increased 53.39 19.86 50 5205 45426 32462845
Polydipsia 50.23 19.86 20 5235 3797 32504474
Suicide attempt 46.72 19.86 43 5212 38201 32470070
White blood cell count increased 41.96 19.86 42 5213 41360 32466911
Overdose 39.83 19.86 59 5196 87018 32421253
Toxicity to various agents 39.48 19.86 88 5167 177953 32330318
Delusion 38.87 19.86 25 5230 13083 32495188
Lymphocyte percentage increased 35.09 19.86 8 5247 220 32508051
Parkinsonism 33.68 19.86 19 5236 7850 32500421
Stupor 33.54 19.86 14 5241 2995 32505276
Intentional overdose 31.21 19.86 36 5219 41565 32466706
Sciatic nerve neuropathy 30.64 19.86 6 5249 77 32508194
Sciatic nerve injury 29.29 19.86 6 5249 98 32508173
Liver disorder 28.24 19.86 30 5225 31624 32476647
Persecutory delusion 26.47 19.86 11 5244 2328 32505943
Hallucination, auditory 26.46 19.86 18 5237 10332 32497939
Insomnia 26.11 19.86 53 5202 100295 32407976
Somnolence 26.04 19.86 54 5201 103743 32404528
Mania 25.22 19.86 17 5238 9615 32498656
Schizophrenia 24.67 19.86 17 5238 9967 32498304
Sudden death 23.28 19.86 20 5235 16212 32492059
Seizure 22.57 19.86 51 5204 103803 32404468
Neonatal asphyxia 22.38 19.86 6 5249 325 32507946
Depressed level of consciousness 22.07 19.86 30 5225 40817 32467454
Delirium 21.78 19.86 31 5224 44015 32464256
Dyspnoea 20.67 19.86 17 5238 362028 32146243
Eosinophil count increased 20.11 19.86 14 5241 8341 32499930

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-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
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
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel Ki 8.70 WOMBAT-PK
GABA-A receptor alpha-2/beta-3/gamma-2 Ion channel Ki 8.70 WOMBAT-PK
GABA-A receptor alpha-3/beta-3/gamma-2 Ion channel Ki 8.35 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-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-3/beta-2/gamma-2 Ion channel Ki 8.82 WOMBAT-PK
GABA A receptor alpha-3/beta-2/gamma-3 Ion channel Ki 7.50 WOMBAT-PK
GABA A receptor alpha-5/beta-3/gamma-3 Ion channel Ki 8.42 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; 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
3380 PUBCHEM_CID
4193 IUPHAR_LIGAND_ID
2951 INN_ID
620X0222FQ UNII
4460 RXNORM
004091 NDDF
387573007 SNOMEDCT_US
96237009 SNOMEDCT_US

Pharmaceutical products:

None