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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=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

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
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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

8.2944E9
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
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
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
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
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
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
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
n = 18
Health Status: healthy
Sex: M
Population Size: 18
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
n = 18
Health Status: healthy
Sex: M
Population Size: 18
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
n = 18
Health Status: healthy
Sex: M
Population Size: 18
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
n = 18
Health Status: healthy
Sex: M
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16702893/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461

OCT2
647
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT2
648
 yes [IC50 60 uM]
P-gp
1650
 yes [IC50 62.5 uM]
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice.
1976
Derivative spectrophotometric method for determination of acidity constants of single step acid-base equilibria.
2001 Aug 30
Determination of Clobazam, Clorazepate, Flurazepam and Flunitrazepam in pharmaceutical preparations.
2002 May 16
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.
2005 Dec
Role of giant depolarizing potentials in shaping synaptic currents in the developing hippocampus.
2006
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
GABAergic signaling at mossy fiber synapses in neonatal rat hippocampus.
2006 Jan 11
Impact of epsilon and theta subunits on pharmacological properties of alpha3beta1 GABAA receptors expressed in Xenopus oocytes.
2006 Jan 13
Sleep maintenance insomnia: strengths and weaknesses of current pharmacologic therapies.
2006 Jan-Mar
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
Acute flurazepam intoxication: a case report.
2006 Mar
A double-blind, placebo-controlled investigation of the residual psychomotor and cognitive effects of zolpidem-MR in healthy elderly volunteers.
2006 Nov
Noninvasive capnometry for continuous monitoring of mental status: a tale of 2 patients.
2006 Oct
Eating and weight related cognitions in people with Schizophrenia : a case control study.
2006 Oct 31
Zolpidem modified-release in insomnia.
2007
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.
2007 Apr
Eszopiclone: its use in the treatment of insomnia.
2007 Aug
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 Aug
Greater incidence of depression with hypnotic use than with placebo.
2007 Aug 21
Agonist-, antagonist-, and benzodiazepine-induced structural changes in the alpha1 Met113-Leu132 region of the GABAA receptor.
2007 Feb
Sensitivity of P-glycoprotein tryptophan residues to benzodiazepines and ATP interaction.
2007 Jan
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
Benzodiazepine receptor agonists affect both binding and gating of recombinant alpha1beta2gamma2 gamma-aminobutyric acid-A receptors.
2007 May 28
Precipitation of long duration hypnic headaches after ACE inhibitor withdrawal.
2007 Nov
GABA transient sets the susceptibility of mIPSCs to modulation by benzodiazepine receptor agonists in rat hippocampal neurons.
2007 Nov 15
Methadone induced torsade de pointes in a patient receiving antiretroviral therapy.
2007 Nov-Dec
Determination of benzodiazepines in oral fluid using LC-MS-MS.
2007 Nov-Dec
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 Sep
Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression.
2008
Increased AMPA receptor GluR1 subunit incorporation in rat hippocampal CA1 synapses during benzodiazepine withdrawal.
2008 Dec 20
Prevalence of contraindications to mefloquine use among USA military personnel deployed to Central Asia.
2008 Feb 11
Flurazepam inhibits the P-glycoprotein transport function: an insight to revert multidrug-resistance phenotype.
2008 Feb 26
Individually monitoring ligand-induced changes in the structure of the GABAA receptor at benzodiazepine binding site and non-binding-site interfaces.
2008 Jul
Subchronic treatment with antiepileptic drugs modifies pentylenetetrazol-induced seizures in mice: Its correlation with benzodiazepine receptor binding.
2008 Jun
Benzodiazepine-mediated structural changes in the multidrug transporter P-glycoprotein: an intrinsic fluorescence quenching analysis.
2008 Jun
Structural mechanisms underlying benzodiazepine modulation of the GABA(A) receptor.
2008 Mar 26
Flurazepam effect on GABAergic currents depends on extracellular pH.
2008 May
Chronic benzodiazepine-induced reduction in GABA(A) receptor-mediated synaptic currents in hippocampal CA1 pyramidal neurons prevented by prior nimodipine injection.
2008 Nov 11
17beta-estradiol affects GABAergic transmission in developing hippocampus.
2008 Nov 19
K+ channel TASK-1 knockout mice show enhanced sensitivities to ataxic and hypnotic effects of GABA(A) receptor ligands.
2008 Oct
Reduced benzodiazepine tolerance, but increased flumazenil-precipitated withdrawal in AMPA-receptor GluR-A subunit-deficient mice.
2009 Apr
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 Apr
Next-day residual effects of gaboxadol and flurazepam administered at bedtime: a randomized double-blind study in healthy elderly subjects.
2009 Jan
Association between risk factors for injurious falls and new benzodiazepine prescribing in elderly persons.
2009 Jan 6
Functional characterization of the human organic cation transporter 2 variant p.270Ala>Ser.
2009 Jun
An epigenetic intervention interacts with genetic strain differences to modulate the stress-induced reduction of flurazepam's antiseizure efficacy in the mouse.
2009 Jun
Metabolism of two new benzodiazepine-type anti-leishmanial agents in rat hepatocytes and hepatic microsomes and their interaction with glutathione in macrophages.
2009 Mar
Towards a basic endoscopic evaluation of swallowing in acute stroke - identification of salient findings by the inexperienced examiner.
2009 Mar 10
Patents

Patents

JP2000511885A
20
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 Fri Dec 15 15:20:49 UTC 2023
Edited
by admin
on Fri Dec 15 15:20:49 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
NDF-RT N0000175694
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
NDF-RT N0000007542
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
WHO-VATC QN05CD01
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
WHO-ATC N05CD01
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
LIVERTOX NBK548683
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
DEA NO. 2767
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
Code System Code Type Description
INN
2551
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
SMS_ID
100000092582
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL968
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
EVMPD
SUB07744MIG
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
RXCUI
4501
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY RxNorm
HSDB
3085
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
DRUG BANK
DB00690
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
FDA UNII
IHP475989U
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
WIKIPEDIA
FLURAZEPAM
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
NCI_THESAURUS
C62030
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
DAILYMED
IHP475989U
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
IUPHAR
7188
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023071
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-591-7
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
MESH
D005479
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
LACTMED
Flurazepam
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
MERCK INDEX
m5498
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY Merck Index
CHEBI
5128
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
CAS
17617-23-1
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
PUBCHEM
3393
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
PRIMARY
DRUG CENTRAL
1218
Created by admin on Fri Dec 15 15:20:49 UTC 2023 , Edited by admin on Fri Dec 15 15:20:49 UTC 2023
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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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