U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H23ClFN3O
Molecular Weight 387.878
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLURAZEPAM

SMILES

CCN(CC)CCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C3=C(F)C=CC=C3

InChI

InChIKey=SAADBVWGJQAEFS-UHFFFAOYSA-N
InChI=1S/C21H23ClFN3O/c1-3-25(4-2)11-12-26-19-10-9-15(22)13-17(19)21(24-14-20(26)27)16-7-5-6-8-18(16)23/h5-10,13H,3-4,11-12,14H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C21H23ClFN3O
Molecular Weight 387.878
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Flurazepam (known under the brand names Dalmane and Dalmadorm) is a drug which is a benzodiazepine derivative. It is a hypnotic agent which does not appear to decrease dream time as measured by rapid eye movements (REM). Furthermore, it decreases sleep latency and number of awakenings for a consequent increase in total sleep time. Flurazepam binds to an allosteric site on GABA-A receptors. Binding potentiates the action of GABA on GABA-A receptors by opening the chloride channel within the receptor, causing chloride influx and hyperpolarization. Flurazepam is useful for the treatment of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakening. Flurazepam can be used effectively in patients with recurring insomnia or poor sleeping habits, and in acute or chronic medical situations requiring restful sleep.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Flurazepam

Approved Use

Flurazepam hydrochloride is a hypnotic agent useful for the treatment of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakening. Flurazepam hydrochloride capsules can be used effectively in patients with recurring insomnia or poor sleeping habits, and in acute or chronic medical situations requiring restful sleep. Sleep laboratory studies have objectively determined that flurazepam hydrochloride capsules are effective for at least 28 consecutive nights of drug administration. Since insomnia is often transient and intermittent, short-term use is usually sufficient. Prolonged use of hypnotics is usually not indicated and should only be undertaken concomitantly with appropriate evaluation of the patient.

Launch Date

1970
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.6 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYETHYL-FLURAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-DESALKYLFLURAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.5 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLURAZEPAM ALDEHYDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYETHYL-FLURAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
75 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-DESALKYLFLURAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.5 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLURAZEPAM ALDEHYDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy
n = 18
Health Status: healthy
Sex: M
Population Size: 18
Sources:
Other AEs: Somnolence, Agitation...
Other AEs:
Somnolence (5 patients)
Agitation (1 patient)
Dizziness (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Agitation 1 patient
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy
n = 18
Health Status: healthy
Sex: M
Population Size: 18
Sources:
Dizziness 1 patient
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy
n = 18
Health Status: healthy
Sex: M
Population Size: 18
Sources:
Somnolence 5 patients
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy
n = 18
Health Status: healthy
Sex: M
Population Size: 18
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 60 uM]
yes [IC50 62.5 uM]
PubMed

PubMed

TitleDatePubMed
The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice.
1976
Sensitive gas chromatographic--mass spectrometric screening of acetylated benzodiazepines.
2001 Feb 23
Carbon monoxide-mediated hippocampal injury.
2001 Jul 10
Selective enhancement of AMPA receptor-mediated function in hippocampal CA1 neurons from chronic benzodiazepine-treated rats.
2002 Jul
The continuing challenge of inappropriate prescribing in the elderly: an update of the evidence.
2002 Nov-Dec
Effects of benzodiazepines on frog ERG.
2003 Apr
H3 agonist immepip markedly reduces cortical histamine release, but only weakly promotes sleep in the rat.
2003 Aug
Residual effects of hypnotics: epidemiology and clinical implications.
2004
Clustering of extrasynaptic GABA(A) receptors modulates tonic inhibition in cultured hippocampal neurons.
2004 Oct 29
'Hypnotic' prescription patterns in a large managed-care population.
2004 Sep
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.
2005 Dec
Modeling cumulative dose and exposure duration provided insights regarding the associations between benzodiazepines and injuries.
2006 Apr
Actions of glutamate and ivermectin on the pharyngeal muscle of Ascaridia galli: a comparative study with Caenorhabditis elegans.
2006 Apr
A double-blind, placebo- and flurazepam-controlled investigation of the residual psychomotor and cognitive effects of modified release zolpidem in young healthy volunteers.
2006 Jun
Eating and weight related cognitions in people with Schizophrenia : a case control study.
2006 Oct 31
Zolpidem modified-release in insomnia.
2007
A simple and reliable procedure for the determination of psychoactive drugs in oral fluid by gas chromatography-mass spectrometry.
2007 Jun 28
Suicide by multidrug ingestion: hypothesis on the role played by the self-administration of activated charcoal.
2007 Mar
GABA transient sets the susceptibility of mIPSCs to modulation by benzodiazepine receptor agonists in rat hippocampal neurons.
2007 Nov 15
Determination of benzodiazepines in oral fluid using LC-MS-MS.
2007 Nov-Dec
Prevalence of contraindications to mefloquine use among USA military personnel deployed to Central Asia.
2008 Feb 11
Benzodiazepine-mediated structural changes in the multidrug transporter P-glycoprotein: an intrinsic fluorescence quenching analysis.
2008 Jun
17beta-estradiol affects GABAergic transmission in developing hippocampus.
2008 Nov 19
Association between risk factors for injurious falls and new benzodiazepine prescribing in elderly persons.
2009 Jan 6
Patents

Sample Use Guides

Usual Adult Dose for Insomnia 15 mg orally once a day at bedtime for women and 15 or 30 mg orally once a day at bedtime for men Comments: -The 15 mg dose can be increased to 30 mg if necessary for efficacy. -The lowest effective dose should be used, since important adverse effects are dose related. -Dosage should be limited to 15 mg per day in elderly or debilitated patients.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: To investigate a possible mechanism of this synergistic interaction between propofol and benzodiazepines, the effect of propofol and flurazepam on GABAA receptor function was examined in Xenopus oocytes expressing recombinant alpha 1 beta 2 gamma 2L and alpha 2 beta 2 gamma 2L receptor constructs.
Potentiation of GABA receptor-activated current by low (1-10 uM) concentrations of propofol together with flurazepam (0.25-0.5 uM) was significantly greater than predicted by an additive response.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:49 GMT 2023
Record UNII
IHP475989U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLURAZEPAM
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
flurazepam [INN]
Common Name English
7-CHLORO-1-(2-(DIETHYLAMINO)ETHYL)-5-(O-FLUOROPHENYL)-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONE
Common Name English
Flurazepam [WHO-DD]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1-(2-(DIETHYLAMINO)ETHYL)-5-(2-FLUOROPHENYL)-1,3-DIHYDRO
Common Name English
FLURAZEPAM [MI]
Common Name English
FLURAZEPAM [JAN]
Common Name English
FLURAZEPAM [MART.]
Common Name English
INSUMIN
Brand Name English
FLURAZEPAM [HSDB]
Common Name English
FLURAZEPAM [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
NDF-RT N0000175694
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
NDF-RT N0000007542
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
WHO-VATC QN05CD01
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
WHO-ATC N05CD01
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
LIVERTOX NBK548683
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
DEA NO. 2767
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
Code System Code Type Description
INN
2551
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
SMS_ID
100000092582
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL968
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
EVMPD
SUB07744MIG
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
RXCUI
4501
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY RxNorm
HSDB
3085
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
DRUG BANK
DB00690
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
FDA UNII
IHP475989U
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
WIKIPEDIA
FLURAZEPAM
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
NCI_THESAURUS
C62030
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
DAILYMED
IHP475989U
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
IUPHAR
7188
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023071
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-591-7
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
MESH
D005479
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
LACTMED
Flurazepam
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
MERCK INDEX
m5498
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY Merck Index
CHEBI
5128
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
CAS
17617-23-1
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
PUBCHEM
3393
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
DRUG CENTRAL
1218
Created by admin on Fri Dec 15 15:20:49 GMT 2023 , Edited by admin on Fri Dec 15 15:20:49 GMT 2023
PRIMARY
Related Record Type Details
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BINDING
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METABOLITE -> PARENT
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC