FLUNITRAZEPAM

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 Search

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
Sources: http://www.medicines.ie/printfriendlydocument.aspx?documentid=1048&companyid=264
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11393809 \| https://www.ncbi.nlm.nih.gov/pubmed/9914279	Positive Allosteric Modulator 179
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095172 Sources: DOI: 10.1111/j.1440-1681.2008.04946.x	Positive Allosteric Modulator 179		0.45 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: http://www.medicines.ie/printfriendlydocument.aspx?documentid=1048&companyid=264	Primary		Approved 8429	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 1982

PubMed

Title	Date	PubMed
Prolonged upper airway instability in the parenteral use of benzodiazepine with levomepromazine.	2000 Feb	10653217
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.	2001 Apr	11327354
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.	2001 Apr	11311894
Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre.	2001 Apr 15	11343860
High-performance liquid chromatography determination of flunitrazepam and its metabolites in plasma by use of column-switching technique: comparison of two extraction columns.	2001 Apr 25	11339271
Flunitrazepam, a 7-nitro-1,4-benzodiazepine that is unable to bind to the indole-benzodiazepine site of human serum albumin.	2001 Apr 7	11295439
Flunitrazepam abuse and personality characteristics in male forensic psychiatric patients.	2001 Aug 5	11472788
Molecular modeling and QSAR analysis of the interaction of flavone derivatives with the benzodiazepine binding site of the GABA(A) receptor complex.	2001 Feb	11249125
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.	2001 Feb	11159802
[Drugs and drug abusers].	2001 Feb 17	11252979
Honokiol and magnolol selectively interact with GABAA receptor subtypes in vitro.	2001 Jul	11408830
Drug-facilitated date rape.	2001 Jul 10	11468961
The association between intravenous haloperidol and prolonged QT interval.	2001 Jun	11386487
Allosteric modulation in spontaneously active mutant gamma-aminobutyric acidA receptors.	2001 Jun 1	11356312
Observation of psychoactive substance consumption: methods and results of the French OPPIDUM programme.	2001 Mar	11316923
Evidence for the formation of functionally distinct alphabetagammaepsilon GABA(A) receptors.	2001 Nov 15	11711565
Serum and urine concentrations of flunitrazepam and metabolites, after a single oral dose, by immunoassay and GC-MS.	2001 Nov-Dec	11765027
Evidence for a role for GABA(A) and NMDA receptors in ethanol inhibition of long-term potentiation.	2001 Oct 19	11597760
Violent behavior, impulsive decision-making, and anterograde amnesia while intoxicated with flunitrazepam and alcohol or other drugs: a case study in forensic psychiatric patients.	2002	12108561
The flunitrazepam abuse prevention program at a general hospital in Taiwan: a descriptive study.	2002 Aug	12109961
[Acute ischemia of the leg in a drug addict].	2002 Feb	11951700
Buprenorphine prescription by general practitioners in a French region.	2002 Jan 1	11772481
Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic.	2002 Jan 2	11755161
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.	2002 Jul 15	12117556
More on Rohypnol.	2002 Jun	12098855
Coordinate release of ATP and GABA at in vitro synapses of lateral hypothalamic neurons.	2002 Jun 15	12077176
Detection of flunitrazepam and 7-aminoflunitrazepam in oral fluid after controlled administration of rohypnol.	2002 May-Jun	12054361

Patents

Sample Use Guides

In Vivo Use Guide

Usual dose 0.5 - 1mg; in exceptional circumstances the dose may be increased to 2mg.

Route of Administration: Oral

In Vitro Use Guide

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

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