FLURAZEPAM MONOHYDROCHLORIDE

First approved in 1970

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H23ClFN3O.ClH
Molecular Weight	424.339
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FLURAZEPAM MONOHYDROCHLORIDE

Structure Search

SMILES

Cl.CCN(CC)CCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C3=CC=CC=C3F

InChI

InChIKey=PUGVROXLRUQCAF-UHFFFAOYSA-N

InChI=1S/C21H23ClFN3O.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/016721s076lbl.pdf | https://www.drugs.com/pro/flurazepam.html

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

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.drugbank.ca/drugs/DB00690 \| https://www.ncbi.nlm.nih.gov/pubmed/6094209 \| https://www.ncbi.nlm.nih.gov/pubmed/2863335	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/016721s076lbl.pdf	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

C_max

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 OCT2 779

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19002438/ Page: 10.0	yes [IC50 60 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18190907/	yes [IC50 62.5 uM]

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Functional characterization of the human organic cation transporter 2 variant p.270Ala>Ser.	2009-06	19251820
An epigenetic intervention interacts with genetic strain differences to modulate the stress-induced reduction of flurazepam's antiseizure efficacy in the mouse.	2009-06	19189880
Reduced benzodiazepine tolerance, but increased flumazenil-precipitated withdrawal in AMPA-receptor GluR-A subunit-deficient mice.	2009-04	19141300
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	18937304
Towards a basic endoscopic evaluation of swallowing in acute stroke - identification of salient findings by the inexperienced examiner.	2009-03-10	19284543
Metabolism of two new benzodiazepine-type anti-leishmanial agents in rat hepatocytes and hepatic microsomes and their interaction with glutathione in macrophages.	2009-03	19222915
Association between risk factors for injurious falls and new benzodiazepine prescribing in elderly persons.	2009-01-06	19126237
Next-day residual effects of gaboxadol and flurazepam administered at bedtime: a randomized double-blind study in healthy elderly subjects.	2009-01	18985628
Increased AMPA receptor GluR1 subunit incorporation in rat hippocampal CA1 synapses during benzodiazepine withdrawal.	2008-12-20	18924138
17beta-estradiol affects GABAergic transmission in developing hippocampus.	2008-11-19	18822277
Chronic benzodiazepine-induced reduction in GABA(A) receptor-mediated synaptic currents in hippocampal CA1 pyramidal neurons prevented by prior nimodipine injection.	2008-11-11	18805463
K+ channel TASK-1 knockout mice show enhanced sensitivities to ataxic and hypnotic effects of GABA(A) receptor ligands.	2008-10	18660435
Individually monitoring ligand-induced changes in the structure of the GABAA receptor at benzodiazepine binding site and non-binding-site interfaces.	2008-07	18424553
Subchronic treatment with antiepileptic drugs modifies pentylenetetrazol-induced seizures in mice: Its correlation with benzodiazepine receptor binding.	2008-06	18830436
Benzodiazepine-mediated structural changes in the multidrug transporter P-glycoprotein: an intrinsic fluorescence quenching analysis.	2008-06	18791834
Flurazepam effect on GABAergic currents depends on extracellular pH.	2008-05	18362897
Structural mechanisms underlying benzodiazepine modulation of the GABA(A) receptor.	2008-03-26	18367615
Flurazepam inhibits the P-glycoprotein transport function: an insight to revert multidrug-resistance phenotype.	2008-02-26	18190907
Methadone induced torsade de pointes in a patient receiving antiretroviral therapy.	2008-02-19	18277734
Prevalence of contraindications to mefloquine use among USA military personnel deployed to Central Asia.	2008-02-11	18267019
Neuroanatomical pattern of mitochondrial complex I pathology varies between schizophrenia, bipolar disorder and major depression.	2008	18989376
Determination of benzodiazepines in oral fluid using LC-MS-MS.	2007-12-21	18093420
GABA transient sets the susceptibility of mIPSCs to modulation by benzodiazepine receptor agonists in rat hippocampal neurons.	2007-11-15	17855751
Precipitation of long duration hypnic headaches after ACE inhibitor withdrawal.	2007-11	17965960
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	17762513
Greater incidence of depression with hypnotic use than with placebo.	2007-08-21	17711589
Eszopiclone: its use in the treatment of insomnia.	2007-08	19300573
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	17510319
A simple and reliable procedure for the determination of psychoactive drugs in oral fluid by gas chromatography-mass spectrometry.	2007-06-28	17395417
Benzodiazepine receptor agonists affect both binding and gating of recombinant alpha1beta2gamma2 gamma-aminobutyric acid-A receptors.	2007-05-28	17471066
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.	2007-04	17496723
Suicide by multidrug ingestion: hypothesis on the role played by the self-administration of activated charcoal.	2007-03	17325466
Agonist-, antagonist-, and benzodiazepine-induced structural changes in the alpha1 Met113-Leu132 region of the GABAA receptor.	2007-02	17108261
Sensitivity of P-glycoprotein tryptophan residues to benzodiazepines and ATP interaction.	2007-01	16919386
Zolpidem modified-release in insomnia.	2007	19300582
A double-blind, placebo-controlled investigation of the residual psychomotor and cognitive effects of zolpidem-MR in healthy elderly volunteers.	2006-11	17061961
Eating and weight related cognitions in people with Schizophrenia : a case control study.	2006-10-31	17076886
Noninvasive capnometry for continuous monitoring of mental status: a tale of 2 patients.	2006-10	16984855
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	16702893
Modeling cumulative dose and exposure duration provided insights regarding the associations between benzodiazepines and injuries.	2006-04	16549262
Actions of glutamate and ivermectin on the pharyngeal muscle of Ascaridia galli: a comparative study with Caenorhabditis elegans.	2006-04	16442540
Sleep maintenance insomnia: strengths and weaknesses of current pharmacologic therapies.	2006-03-07	16517453
Acute flurazepam intoxication: a case report.	2006-03	16501350
Impact of epsilon and theta subunits on pharmacological properties of alpha3beta1 GABAA receptors expressed in Xenopus oocytes.	2006-01-13	16412217
GABAergic signaling at mossy fiber synapses in neonatal rat hippocampus.	2006-01-11	16407558
Role of giant depolarizing potentials in shaping synaptic currents in the developing hippocampus.	2006	17725505
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.	2005-12	18360572
Determination of Clobazam, Clorazepate, Flurazepam and Flunitrazepam in pharmaceutical preparations.	2002-05-16	18968634
Derivative spectrophotometric method for determination of acidity constants of single step acid-base equilibria.	2001-08-30	18968381
The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice.	1976	18375

Patents

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

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 19:29:17 GMT 2025` Edited by `admin` on `Mon Mar 31 19:29:17 GMT 2025`
Record UNII	7C4JH842IJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1-(2-(DIETHYLAMINO)ETHYL)-5-(2-FLUOROPHENYL)-1,3-DIHYDRO-, MONOHYDROCHLORIDE

Preferred Name

English

FLURAZEPAM MONOHYDROCHLORIDE

Common Name

English

FLURAZEPAM MONOHYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

FLURAZEPAM MONOHYDROCHLORIDE [MART.]

Common Name

English

2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1-(2-(DIETHYLAMINO)ETHYL)-5-(2-FLUOROPHENYL)-1,3-DIHYDRO-, HYDROCHLORIDE (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1012