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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12FN3O3
Molecular Weight 313.2832
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUNITRAZEPAM

SMILES

CN1C2=C(C=C(C=C2)[N+]([O-])=O)C(=NCC1=O)C3=C(F)C=CC=C3

InChI

InChIKey=PPTYJKAXVCCBDU-UHFFFAOYSA-N
InChI=1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://en.pharmacodia.com/yaodu/html/v1/chemicals/f0782c53cab465685c663c70eb6d85e5.html | https://www.drugs.com/illicit/rohypnol.html

Flunitrazepam is an intermediate-acting benzodiazepine with general properties similar to those of diazepam. It is generally intended to be for short-term treatment for chronic or severe insomniacs who are unresponsive to other hypnotics. The main pharmacological effects of Flunitrazepam are the enhancement of GABA at the GABAA receptor. The physical effects of Flunitrazepam include sedation, muscle relaxation, decreased anxiety, and prevention of convulsions. It causes partial amnesia; individuals are unable to remember certain events that they experience while under the influence of the drug. Chronic use of Flunitrazepam can result in physical dependence and the appearance of a withdrawal syndrome when the drug is discontinued. Flunitrazepam impairs cognitive and psychomotor functions affecting reaction time and driving skill. The use of this drug in combination with alcohol is a particular concern as both central nervous system depressants potentiate each other's toxicity.

Originator

Curator's Comment: # Hoffmann La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2095172
Sources: DOI: 10.1111/j.1440-1681.2008.04946.x
0.45 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Rohypnol

Approved Use

Rohypnol is generally intended to be for short-term treatment for chronic or severe insomniacs who are unresponsive to other hypnotics.

Launch Date

3.92515191E11
PubMed

PubMed

TitleDatePubMed
A puzzling case of seizures and visual hallucinations during clomipramine treatment with a high dose but causing a low serum concentration.
1999 May
Mimicking gene defects to treat drug dependence.
2000
Convulsive status epilepticus following abrupt high-dose benzodiazepine discontinuation.
2000 Apr 1
Prolonged upper airway instability in the parenteral use of benzodiazepine with levomepromazine.
2000 Feb
Neocortical hyperexcitability after GABA withdrawal in vitro.
2000 Mar
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.
2001 Apr
Tolerance to midazolam's anxiolytic effects after short-term nicotine treatment.
2001 Apr
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.
2001 Apr
Identification of amino acid residues responsible for the alpha5 subunit binding selectivity of L-655,708, a benzodiazepine binding site ligand at the GABA(A) receptor.
2001 Apr
Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4.
2001 Apr
Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre.
2001 Apr 15
Flunitrazepam, a 7-nitro-1,4-benzodiazepine that is unable to bind to the indole-benzodiazepine site of human serum albumin.
2001 Apr 7
[Clonidine combined with flunitrazepam before carotid endarterectomy decreases cerebrovascular CO2 reactivity].
2001 Aug
Density and distribution of hippocampal neurotransmitter receptors in autism: an autoradiographic study.
2001 Dec
Molecular modeling and QSAR analysis of the interaction of flavone derivatives with the benzodiazepine binding site of the GABA(A) receptor complex.
2001 Feb
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.
2001 Feb
Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation.
2001 Feb 12
[Rohypnol--a narcotic drug].
2001 Feb 21
Sensitive gas chromatographic--mass spectrometric screening of acetylated benzodiazepines.
2001 Feb 23
Heterogeneity of hippocampal GABA(A) receptors: regulation by corticosterone.
2001 Jan 1
[Plastic bag as the method in suicide and homicide].
2001 Jan-Feb
Activation of GABA(A) receptors in subthalamic neurons in vitro: properties of native receptors and inhibition mechanisms.
2001 Jul
Patient information. Date rape drugs: what parents should know.
2001 Jun
The association between intravenous haloperidol and prolonged QT interval.
2001 Jun
Allosteric modulation in spontaneously active mutant gamma-aminobutyric acidA receptors.
2001 Jun 1
Behavioral effects of flunitrazepam: reinforcing and discriminative stimulus effects in rhesus monkeys and prevention of withdrawal signs in pentobarbital-dependent rats.
2001 Jun 1
Analytical methodology for the detection of benzodiazepine consumption in opioid-dependent subjects.
2001 Mar
Regional distribution of benzodiazepine binding sites in the human newborn and infant hypothalamus. A quantitative autoradiographic study.
2001 Mar 23
In ovo chronic neurosteroid treatment affects the function and allosteric interactions of GABA(A) receptor modulatory sites.
2001 May 25
Differential sensitivity to the anxiolytic effects of ethanol and flunitrazepam in PKCgamma null mutant mice.
2001 May-Jun
Modulation of rate of onset and intensity of drug effects reduces abuse potential in healthy males.
2001 Nov 1
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
2001 Nov 15
3Alpha-hydroxy-5alpha-pregnan-20-one levels and GABA(A) receptor-mediated 36Cl(-) flux across development in rat cerebral cortex.
2001 Nov 26
Mutagenesis of the GABA(A) receptor alpha1 subunit reveals a domain that affects sensitivity to GABA and benzodiazepine-site ligands.
2001 Oct
Distinct signal transduction pathways for GABA-induced GABA(A) receptor down-regulation and uncoupling in neuronal culture: a role for voltage-gated calcium channels.
2001 Sep
A novel approach to the prevention of postoperative delirium in the elderly after gastrointestinal surgery.
2002
[Crime under the influence of psychoactive drugs: the problem of the duration of detection].
2002
Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines.
2002 Apr
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.
2002 Jul 15
Club drugs: methylenedioxymethamphetamine, flunitrazepam, ketamine hydrochloride, and gamma-hydroxybutyrate.
2002 Jun 1
Coordinate release of ATP and GABA at in vitro synapses of lateral hypothalamic neurons.
2002 Jun 15
Drugged and sexually assaulted.
2002 Mar
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].
2002 Mar-Apr
Tolterodine-associated acute mixed liver injury.
2002 May
Patents

Sample Use Guides

Usual dose 0.5 - 1mg; in exceptional circumstances the dose may be increased to 2mg.
Route of Administration: Oral
The binding affinity for [3H]flunitrazepam was most affected in the hippocampus where there was a significant drug ×time interaction (F4,49= 4.6, p<0.01).
Name Type Language
FLUNITRAZEPAM
EP   HSDB   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
FLUNITRAZEPAM [USAN]
Common Name English
FLUNITRAZEPAM [EP MONOGRAPH]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-
Systematic Name English
RO-54200
Code English
5-(O-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-2H-1,4-BENZODIAZEPIN-2-ONE
Common Name English
ROHYPNOL
Brand Name English
Flunitrazepam [WHO-DD]
Common Name English
FLUNITRAZEPAM [MI]
Common Name English
FLUNITRAZEPAM [HSDB]
Common Name English
FLUNITRAZEPAM [JAN]
Common Name English
flunitrazepam [INN]
Common Name English
FLUNITRAZEPAM [MART.]
Common Name English
RO-5-4200
Code English
RO 5-4200
Code English
N05CD03
Code English
Classification Tree Code System Code
WHO-VATC QN05CD03
Created by admin on Fri Dec 15 15:05:22 UTC 2023 , Edited by admin on Fri Dec 15 15:05:22 UTC 2023
DEA NO. 2763
Created by admin on Fri Dec 15 15:05:22 UTC 2023 , Edited by admin on Fri Dec 15 15:05:22 UTC 2023
NCI_THESAURUS C1012
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WHO-ATC N05CD03
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Code System Code Type Description
IUPHAR
4193
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PRIMARY
FDA UNII
620X0222FQ
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MERCK INDEX
m5447
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PRIMARY Merck Index
ChEMBL
CHEMBL13280
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DRUG CENTRAL
1202
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PRIMARY
CAS
1622-62-4
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EPA CompTox
DTXSID7023065
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SMS_ID
100000092658
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CHEBI
31622
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PRIMARY
HSDB
6960
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PRIMARY
PUBCHEM
3380
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RXCUI
4460
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PRIMARY RxNorm
WIKIPEDIA
FLUNITRAZEPAM
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PRIMARY
INN
2951
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PRIMARY
DRUG BANK
DB01544
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PRIMARY
MESH
D005445
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PRIMARY
NCI_THESAURUS
C87672
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PRIMARY
ECHA (EC/EINECS)
216-597-8
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PRIMARY
EVMPD
SUB07710MIG
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PRIMARY
LACTMED
Flunitrazepam
Created by admin on Fri Dec 15 15:05:22 UTC 2023 , Edited by admin on Fri Dec 15 15:05:22 UTC 2023
PRIMARY