FLUNITRAZEPAM HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12FN3O3.ClH
Molecular Weight	349.744
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FLUNITRAZEPAM HYDROCHLORIDE

SMILES

Cl.CN1C2=CC=C(C=C2C(=NCC1=O)C3=CC=CC=C3F)[N+]([O-])=O

InChI

InChIKey=ABHSFYRSFUICJR-UHFFFAOYSA-N

InChI=1S/C16H12FN3O3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	C16H12FN3O3
Molecular Weight	313.2832
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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 203	Positive Allosteric Modulator 186
GABA-A receptor; alpha-1/beta-2/gamma-2 28	Positive Allosteric Modulator 186		0.45 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111	Primary		Approved 8,583	Rohypnol

C_max

Value	Dose	Analyte	Population
21.7 ng/mL	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
10.2 ng/mL	2 mg 1 times / day multiple, oral	FLUNITRAZEPAM blood	Homo sapiens
12.2 ng/mL	2 mg 1 times / day steady-state, oral	FLUNITRAZEPAM blood	Homo sapiens
12.9 ng/mL	2 mg 1 times / day steady-state, oral	FLUNITRAZEPAM blood	Homo sapiens
47.5 ng/mL	2 mg single, intravenous	FLUNITRAZEPAM blood	Homo sapiens
11.5 ng/mL	2 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens
25 ng/mL	4 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens
12.9 ng/mL	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
13.1 ng/mL	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
9.2 ng/mL	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
203 ng × h/mL	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
232.8 ng × h/mL	2 mg single, intravenous	FLUNITRAZEPAM blood	Homo sapiens
116.7 ng × h/mL	2 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens
240.2 ng × h/mL	4 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
21.2 h	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
24 h	2 mg single, intravenous	FLUNITRAZEPAM blood	Homo sapiens
6.8 h	2 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens
6.2 h	4 mg single, oral	FLUNITRAZEPAM blood	Homo sapiens
22.5 h	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
25.3 h	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens
20.2 h	2 mg single, oral	FLUNITRAZEPAM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
20.4%			FLUNITRAZEPAM plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
8 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Other AEs: Drowsiness, Hypotonia...
1.3 mg/kg single, intravenous Highest studied dose	unhealthy, ADULT	Other AEs: Respiratory depression...

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AEs

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AE	Dose	Population
Drowsiness	8 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Hypotonia	8 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Respiratory depression	1.3 mg/kg single, intravenous Highest studied dose	unhealthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193	substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP2E1 729 P-gp 2,052 CYP2C19 1,119 CYP1A2 1,197 CYP2A6 626 CYP2C8 810

Drug as victim

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Target	Modality	Activity
CYP3A4 1,946	substrate 4,014	major [Km 155 uM]
CYP2B6 776	substrate 4,014	minor [Km 101 uM]
CYP2A6 626	substrate 4,014	minor [Km 1921 uM]
CYP2C9 1,193	substrate 4,014	minor [Km 50 uM]
CYP2C19 1,119	substrate 4,014	minor [Km 60 uM]

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PubMed

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Title	Date	PubMed
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.	2001 Apr	11327354
Tolerance to midazolam's anxiolytic effects after short-term nicotine treatment.	2001 Apr	11311899
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

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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).

Substance Class	Chemical
Record UNII	8L46R3P7MF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-, HYDROCHLORIDE (1:1)

Preferred Name

English

FLUNITRAZEPAM HYDROCHLORIDE

Common Name

English

2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-, MONOHYDROCHLORIDE

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

8L46R3P7MF

PRIMARY

PUBCHEM

156028042

PRIMARY

CAS

88280-25-5

PRIMARY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound