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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=CC=C(Cl)C=C2C(=NCC1=O)C3=CC=CC=C3F

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

Description

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.

CNS Activity

Originator

Approval Year

1970
61
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
186
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
2.5 ng/mL
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
14 ng/mL
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
2.5 h
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
75 h
OTHER
https://pdf.hres.ca/dpd_pm/00013427.PDF
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
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:
https://pubmed.ncbi.nlm.nih.gov/16702893/
healthy
Health Status: healthy
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
Other AEs: Somnolence, Agitation...
Other AEs:
Somnolence (5 patients)
Agitation (1 patient)
Dizziness (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
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:
https://pubmed.ncbi.nlm.nih.gov/16702893/
healthy
Health Status: healthy
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
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:
https://pubmed.ncbi.nlm.nih.gov/16702893/
healthy
Health Status: healthy
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
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:
https://pubmed.ncbi.nlm.nih.gov/16702893/
healthy
Health Status: healthy
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741

OCT2
779
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT2
782
 yes [IC50 60 uM]
P-gp
1932
 yes [IC50 62.5 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:5128
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5128
eMolecules
1986868
https://www.emolecules.com/cgi-bin/more?vid=1986868
ZINC
ZINC000000537752
http://zinc15.docking.org/substances/ZINC000000537752
PubMed

PubMed

TitleDatePubMed
Functional characterization of the human organic cation transporter 2 variant p.270Ala>Ser.
2009-06
An epigenetic intervention interacts with genetic strain differences to modulate the stress-induced reduction of flurazepam's antiseizure efficacy in the mouse.
2009-06
Reduced benzodiazepine tolerance, but increased flumazenil-precipitated withdrawal in AMPA-receptor GluR-A subunit-deficient mice.
2009-04
Simultaneous determination of benzodiazepines and their metabolites in human serum by liquid chromatography-tandem mass spectrometry using a high-resolution octadecyl silica column compatible with aqueous compounds.
2009-04
Towards a basic endoscopic evaluation of swallowing in acute stroke - identification of salient findings by the inexperienced examiner.
2009-03-10
Metabolism of two new benzodiazepine-type anti-leishmanial agents in rat hepatocytes and hepatic microsomes and their interaction with glutathione in macrophages.
2009-03
Association between risk factors for injurious falls and new benzodiazepine prescribing in elderly persons.
2009-01-06
Next-day residual effects of gaboxadol and flurazepam administered at bedtime: a randomized double-blind study in healthy elderly subjects.
2009-01
Increased AMPA receptor GluR1 subunit incorporation in rat hippocampal CA1 synapses during benzodiazepine withdrawal.
2008-12-20
17beta-estradiol affects GABAergic transmission in developing hippocampus.
2008-11-19
Chronic benzodiazepine-induced reduction in GABA(A) receptor-mediated synaptic currents in hippocampal CA1 pyramidal neurons prevented by prior nimodipine injection.
2008-11-11
K+ channel TASK-1 knockout mice show enhanced sensitivities to ataxic and hypnotic effects of GABA(A) receptor ligands.
2008-10
Individually monitoring ligand-induced changes in the structure of the GABAA receptor at benzodiazepine binding site and non-binding-site interfaces.
2008-07
Subchronic treatment with antiepileptic drugs modifies pentylenetetrazol-induced seizures in mice: Its correlation with benzodiazepine receptor binding.
2008-06
Benzodiazepine-mediated structural changes in the multidrug transporter P-glycoprotein: an intrinsic fluorescence quenching analysis.
2008-06
Flurazepam effect on GABAergic currents depends on extracellular pH.
2008-05
Structural mechanisms underlying benzodiazepine modulation of the GABA(A) receptor.
2008-03-26
Flurazepam inhibits the P-glycoprotein transport function: an insight to revert multidrug-resistance phenotype.
2008-02-26
Methadone induced torsade de pointes in a patient receiving antiretroviral therapy.
2008-02-19
Prevalence of contraindications to mefloquine use among USA military personnel deployed to Central Asia.
2008-02-11
Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression.
2008
Determination of benzodiazepines in oral fluid using LC-MS-MS.
2007-12-21
GABA transient sets the susceptibility of mIPSCs to modulation by benzodiazepine receptor agonists in rat hippocampal neurons.
2007-11-15
Precipitation of long duration hypnic headaches after ACE inhibitor withdrawal.
2007-11
Benzodiazepine-induced hippocampal CA1 neuron alpha-amino-3-hydroxy-5-methylisoxasole-4-propionic acid (AMPA) receptor plasticity linked to severity of withdrawal anxiety: differential role of voltage-gated calcium channels and N-methyl-D-aspartic acid receptors.
2007-09
Greater incidence of depression with hypnotic use than with placebo.
2007-08-21
Eszopiclone: its use in the treatment of insomnia.
2007-08
Benzodiazepine withdrawal-induced glutamatergic plasticity involves up-regulation of GluR1-containing alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptors in Hippocampal CA1 neurons.
2007-08
A simple and reliable procedure for the determination of psychoactive drugs in oral fluid by gas chromatography-mass spectrometry.
2007-06-28
Benzodiazepine receptor agonists affect both binding and gating of recombinant alpha1beta2gamma2 gamma-aminobutyric acid-A receptors.
2007-05-28
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.
2007-04
Suicide by multidrug ingestion: hypothesis on the role played by the self-administration of activated charcoal.
2007-03
Agonist-, antagonist-, and benzodiazepine-induced structural changes in the alpha1 Met113-Leu132 region of the GABAA receptor.
2007-02
Sensitivity of P-glycoprotein tryptophan residues to benzodiazepines and ATP interaction.
2007-01
Zolpidem modified-release in insomnia.
2007
A double-blind, placebo-controlled investigation of the residual psychomotor and cognitive effects of zolpidem-MR in healthy elderly volunteers.
2006-11
Eating and weight related cognitions in people with Schizophrenia : a case control study.
2006-10-31
Noninvasive capnometry for continuous monitoring of mental status: a tale of 2 patients.
2006-10
A double-blind, placebo- and flurazepam-controlled investigation of the residual psychomotor and cognitive effects of modified release zolpidem in young healthy volunteers.
2006-06
Modeling cumulative dose and exposure duration provided insights regarding the associations between benzodiazepines and injuries.
2006-04
Actions of glutamate and ivermectin on the pharyngeal muscle of Ascaridia galli: a comparative study with Caenorhabditis elegans.
2006-04
Sleep maintenance insomnia: strengths and weaknesses of current pharmacologic therapies.
2006-03-07
Acute flurazepam intoxication: a case report.
2006-03
Impact of epsilon and theta subunits on pharmacological properties of alpha3beta1 GABAA receptors expressed in Xenopus oocytes.
2006-01-13
GABAergic signaling at mossy fiber synapses in neonatal rat hippocampus.
2006-01-11
Role of giant depolarizing potentials in shaping synaptic currents in the developing hippocampus.
2006
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.
2005-12
Determination of Clobazam, Clorazepate, Flurazepam and Flunitrazepam in pharmaceutical preparations.
2002-05-16
Derivative spectrophotometric method for determination of acidity constants of single step acid-base equilibria.
2001-08-30
The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice.
1976
Patents

Patents

JP2000511885A
22
JPS6261929A
7

Sample Use Guides

In Vivo Use Guide
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 Mon Mar 31 17:54:45 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:45 GMT 2025
Record UNII
IHP475989U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INSUMIN
Preferred Name English
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
FLURAZEPAM [HSDB]
Common Name English
FLURAZEPAM [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1012
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
NDF-RT N0000175694
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
NDF-RT N0000007542
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
WHO-VATC QN05CD01
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
WHO-ATC N05CD01
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
LIVERTOX NBK548683
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
DEA NO. 2767
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
Code System Code Type Description
INN
2551
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
SMS_ID
100000092582
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL968
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
EVMPD
SUB07744MIG
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
RXCUI
4501
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY RxNorm
HSDB
3085
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
DRUG BANK
DB00690
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
FDA UNII
IHP475989U
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
WIKIPEDIA
FLURAZEPAM
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
NCI_THESAURUS
C62030
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
DAILYMED
IHP475989U
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
IUPHAR
7188
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023071
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
ECHA (EC/EINECS)
241-591-7
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
MESH
D005479
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
LACTMED
Flurazepam
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
MERCK INDEX
m5498
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY Merck Index
CHEBI
5128
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
CAS
17617-23-1
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
PUBCHEM
3393
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
DRUG CENTRAL
1218
Created by admin on Mon Mar 31 17:54:45 GMT 2025 , Edited by admin on Mon Mar 31 17:54:45 GMT 2025
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OCT-2
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of RO-7-2750 GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of DIDESETHYLFLURAZEPAM
METABOLITE -> PARENT
URINE
Structure of NORFLURAZEPAM
METABOLITE ACTIVE -> PARENT
Structure of MONODESETHYLFLURAZEPAM
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of N1-(2-HYDROXYETHYL)FLURAZEPAM
METABOLITE -> PARENT
PLASMA
Related Record Type Details
Structure of FLURAZEPAM
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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