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
Overdose 171.40 118.67 41 179 19866 2337999
Intentional overdose 154.30 118.67 34 186 11287 2346578

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
Toxicity to various agents 135.25 76.80 41 180 29100 1717460
Overdose 105.39 76.80 30 191 16671 1729889
Rhabdomyolysis 102.79 76.80 27 194 11063 1735497
Neuroleptic malignant syndrome 100.71 76.80 21 200 3127 1743433

Pharmacologic Action:

SourceCodeDescription
ATC N05CD03 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Benzodiazepine derivatives
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:91016 GABAA receptor agonist
CHEBI has role CHEBI:35474 anxiolytic drug
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

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

Pharmaceutical products:

None