flunitrazepam ๐Ÿถ Veterinary Use | 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 ยตM/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 141.30 26.21 75 3770 74077 63411100
Neuroleptic malignant syndrome 125.09 26.21 41 3804 12015 63473162
Altered state of consciousness 112.40 26.21 46 3799 25184 63459993
Overdose 103.65 26.21 72 3773 115006 63370171
Suicide attempt 97.64 26.21 55 3790 60863 63424314
Salivary hypersecretion 87.35 26.21 28 3817 7638 63477539
Hepatic function abnormal 71.84 26.21 38 3807 37104 63448073
Psychiatric symptom 63.30 26.21 20 3825 5203 63479974
Extrapyramidal disorder 61.79 26.21 25 3820 13259 63471918
Toxicity to various agents 53.32 26.21 70 3775 247180 63237997
Loss of consciousness 52.67 26.21 49 3796 118072 63367105
Pneumonia aspiration 52.09 26.21 30 3815 34510 63450667
Blood creatine phosphokinase increased 50.12 26.21 28 3817 30402 63454775
Parkinsonism 49.77 26.21 20 3825 10419 63474758
Electrocardiogram QT prolonged 46.02 26.21 34 3811 59496 63425681
Drowning 42.42 26.21 9 3836 484 63484693
Hypothermia 41.52 26.21 19 3826 13562 63471615
Stevens-Johnson syndrome 41.19 26.21 23 3822 24927 63460250
Delusion 40.51 26.21 18 3827 11999 63473178
Lymphocytosis 39.44 26.21 12 3833 2755 63482422
Peritoneal perforation 34.02 26.21 6 3839 120 63485057
Carcinoid tumour of the stomach 32.33 26.21 6 3839 161 63485016
Brain injury 31.87 26.21 13 3832 7030 63478147
White blood cell count increased 31.51 26.21 25 3820 48536 63436641
Malignant catatonia 31.25 26.21 6 3839 194 63484983
Lip erosion 31.19 26.21 8 3837 985 63484192
Pyrexia 30.39 26.21 79 3766 470399 63014778
Electrocardiogram J wave abnormal 30.14 26.21 4 3841 9 63485168
Respiratory depression 29.26 26.21 15 3830 13700 63471477
Toxic epidermal necrolysis 27.89 26.21 18 3827 25316 63459861
Pain 26.98 26.21 6 3839 740622 62744555
Water intoxication 26.71 26.21 6 3839 421 63484756
Aspiration 26.48 26.21 13 3832 10838 63474339
Cerebral infarction 26.36 26.21 17 3828 23876 63461301

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 123.55 20.45 54 4057 17880 34934940
Hepatic function abnormal 77.71 20.45 54 4057 44309 34908511
Altered state of consciousness 76.27 20.45 42 4069 22851 34929969
Pneumonia aspiration 71.03 20.45 50 4061 41853 34910967
Rhabdomyolysis 69.12 20.45 60 4051 68103 34884717
Salivary hypersecretion 56.15 20.45 25 4086 8619 34944201
Asphyxia 55.00 20.45 23 4088 6812 34946008
Blood creatine phosphokinase increased 52.67 20.45 43 4068 44814 34908006
Water intoxication 42.98 20.45 10 4101 418 34952402
Overdose 42.69 20.45 53 4058 91006 34861814
Lymphocyte percentage increased 38.24 20.45 8 4103 203 34952617
Toxicity to various agents 38.09 20.45 77 4034 200285 34752535
White blood cell count increased 37.23 20.45 34 4077 41117 34911703
Suicide attempt 36.72 20.45 33 4078 39083 34913737
Delusion 36.15 20.45 21 4090 12614 34940206
Parkinsonism 35.81 20.45 18 4093 8120 34944700
Intentional overdose 35.50 20.45 34 4077 43640 34909180
Sciatic nerve neuropathy 33.91 20.45 6 4105 60 34952760
Psychiatric symptom 32.27 20.45 13 4098 3500 34949320
Adrenergic syndrome 31.31 20.45 6 4105 96 34952724
Stupor 31.12 20.45 12 4099 2879 34949941
Sciatic nerve injury 31.02 20.45 6 4105 101 34952719
Polydipsia 27.60 20.45 12 4099 3903 34948917
Neonatal asphyxia 23.85 20.45 6 4105 349 34952471
Circulatory collapse 22.24 20.45 19 4092 21019 34931801
Persecutory delusion 21.82 20.45 9 4102 2571 34950249
Somnolence 21.39 20.45 43 4068 111073 34841747
Hyperthermia 21.16 20.45 14 4097 10563 34942257

FDA Adverse Event Reporting System (Geriatric)

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 238.86 20.56 93 7765 27466 79709064
Altered state of consciousness 170.03 20.56 84 7774 43738 79692792
Hepatic function abnormal 142.38 20.56 89 7769 73018 79663512
Salivary hypersecretion 141.10 20.56 53 7805 14171 79722359
Intentional overdose 127.89 20.56 96 7762 105864 79630666
Pneumonia aspiration 114.19 20.56 75 7783 66892 79669638
Suicide attempt 104.19 20.56 77 7781 82855 79653675
Overdose 103.27 20.56 108 7750 184098 79552432
Psychiatric symptom 95.24 20.56 33 7825 7002 79729528
Blood creatine phosphokinase increased 93.59 20.56 66 7792 66024 79670506
Rhabdomyolysis 91.42 20.56 78 7780 103053 79633477
Parkinsonism 80.15 20.56 37 7821 16547 79719983
Delusion 78.70 20.56 39 7819 20384 79716146
White blood cell count increased 71.38 20.56 59 7799 74574 79661956
Extrapyramidal disorder 58.14 20.56 33 7825 22646 79713884
Water intoxication 53.89 20.56 13 7845 761 79735769
Toxicity to various agents 53.59 20.56 124 7734 421416 79315114
Asphyxia 46.99 20.56 23 7835 11697 79724833
Cerebral infarction 41.35 20.56 35 7823 45641 79690889
Dyspnoea 40.49 20.56 17 7841 857008 78879522
Pyrexia 40.14 20.56 152 7706 678557 79057973
Pain 38.32 20.56 11 7847 703791 79032739
Stupor 35.29 20.56 16 7842 6856 79729674
Lymphocyte percentage increased 34.55 20.56 9 7849 720 79735810
Depressed level of consciousness 32.94 20.56 44 7814 96608 79639922
Liver disorder 32.75 20.56 38 7820 72379 79664151
Hallucination, auditory 32.39 20.56 22 7836 20671 79715859
Electrocardiogram QT prolonged 32.11 20.56 42 7816 90344 79646186
Lip erosion 31.91 20.56 10 7848 1550 79734980
Loss of consciousness 31.40 20.56 58 7800 167885 79568645
Sudden death 30.72 20.56 22 7836 22489 79714041
Schizophrenia 30.51 20.56 19 7839 15421 79721109
Ileus paralytic 30.18 20.56 16 7842 9604 79726926
Adrenergic syndrome 29.86 20.56 6 7852 149 79736381
Polydipsia 29.62 20.56 14 7844 6591 79729939
Peritoneal perforation 29.10 20.56 6 7852 170 79736360
Carcinoid tumour of the stomach 28.36 20.56 6 7852 193 79736337
Hypothermia 28.25 20.56 21 7837 22725 79713805
Aspiration 28.20 20.56 20 7838 20138 79716392
Electrocardiogram J wave abnormal 28.19 20.56 4 7854 9 79736521
Neutrophil count increased 27.58 20.56 23 7835 29373 79707157
Lymphocytosis 27.54 20.56 12 7846 4681 79731849
Stevens-Johnson syndrome 27.49 20.56 26 7832 39140 79697390
Blood lactate dehydrogenase increased 27.49 20.56 26 7832 39144 79697386
Heat illness 26.75 20.56 7 7851 570 79735960
Fatigue 26.18 20.56 32 7826 929695 78806835
Somnolence 25.68 20.56 66 7792 238915 79497615
Brain injury 24.87 20.56 15 7843 11502 79725028
Brain oedema 24.18 20.56 20 7838 25243 79711287
Glucose tolerance impaired 24.11 20.56 13 7845 8071 79728459
Persecutory delusion 23.86 20.56 11 7847 4898 79731632
Restlessness 23.75 20.56 26 7832 46466 79690064
Sciatic nerve neuropathy 23.55 20.56 6 7852 440 79736090
Arthralgia 22.97 20.56 14 7844 571789 79164741
White blood cell count decreased 22.32 20.56 54 7804 188234 79548296
Sciatic nerve injury 22.08 20.56 6 7852 565 79735965
Suicidal ideation 21.89 20.56 32 7826 76308 79660222
Asthenia 21.29 20.56 12 7846 511677 79224853
Neutrophil percentage increased 21.21 20.56 10 7848 4679 79731851
Seizure 21.16 20.56 53 7805 188781 79547749
Pain in extremity 21.12 20.56 5 7853 364533 79371997
Withdrawal syndrome 21.12 20.56 19 7839 26835 79709695

FDA Adverse Event Reporting System (Pediatric)

None

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 anti-anxiety agents
CHEBI has role CHEBI:35717 hypnotics
CHEBI has role CHEBI:91016 GABAA receptor agonists

Drug Use | Suggest Off label Use Form| |View source of the data|

None




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

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