Flurazepam

Identification

Name

Flurazepam

Accession Number

DB00690  (APRD00983)

Type

Small Molecule

Groups

Approved, Illicit, Investigational

Description

A benzodiazepine derivative used mainly as a hypnotic.

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Flurazepam (DB00690)

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Synonyms

• Flurazepam
• Flurazépam
• Flurazepamum

External IDs

ID 480 / Ro 5-6901

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Flurazepam hydrochloride	7C4JH842IJ	36105-20-1	PUGVROXLRUQCAF-UHFFFAOYSA-N

Product Images

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Dalmane	Capsule		Oral	Valeant Canada Lp Valeant Canada S.E.C.	1971-12-31	2016-07-08
Dalmane	Capsule		Oral	Valeant Canada Lp Valeant Canada S.E.C.	1971-12-31	2016-07-08
Flurazepam	Capsule	15 mg	Oral	Aa Pharma Inc	1982-12-31	Not applicable
Flurazepam	Capsule	30 mg	Oral	Aa Pharma Inc	1982-12-31	Not applicable
Flurazepam 15	Capsule		Oral	Pro Doc Limitee	1982-12-31	2018-04-18
Flurazepam 15mg Capsule	Capsule		Oral	Laboratoires Confab Inc	Not applicable	Not applicable
Flurazepam 30	Capsule		Oral	Pro Doc Limitee	1982-12-31	2017-06-30
Flurazepam 30mg Capsule	Capsule		Oral	Laboratoires Confab Inc	Not applicable	Not applicable
Som-pam	Capsule		Oral	Biomed Pharma	1981-12-31	Not applicable
Som-pam	Capsule		Oral	Biomed Pharma	1981-12-31	Not applicable

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Bio-flurazepam	Capsule		Oral	Biomed Pharma	2004-04-23	Not applicable
Bio-flurazepam	Capsule		Oral	Biomed Pharma	2004-04-23	Not applicable
Flurazepam	Capsule	30 mg/1	Oral	Golden State Medical Supply	1986-12-08	2017-01-02
Flurazepam	Capsule	15 mg/1	Oral	Golden State Medical Supply	1986-12-08	2017-01-02
Flurazepam	Capsule	30 mg/1	Oral	A S Medication Solutions	1986-12-08	Not applicable
Flurazepam	Capsule	15 mg/1	Oral	bryant ranch prepack	1986-12-08	2014-01-01
Flurazepam	Capsule	15 mg/1	Oral	A S Medication Solutions	1986-12-08	Not applicable
Flurazepam	Capsule	30 mg/1	Oral	Preferred Pharmaceuticals, Inc	2012-01-27	2019-09-24
Flurazepam	Capsule	30 mg/1	Oral	Rebel Distributors	1986-12-08	Not applicable
Flurazepam	Capsule	30 mg/1	Oral	Hikma Pharmaceuticals USA Inc.	1986-12-08	2015-01-18

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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International/Other Brands

Dalmadorm (Meda) / Dalmadorm medium (Meda) / Felison (SIT) / Flunox (Teofarma) / Insumin / Sompan (I.C.N.) / Valdorm (Valeas)

Categories

• Anti-Anxiety Agents
• Benzazepines
• Benzodiazepines and benzodiazepine derivatives
• Benzodiazepinones
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP2A6 Substrates
• Cytochrome P-450 CYP2E1 Inhibitors
• Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• GABA Agents
• GABA Modulators
• Heterocyclic Compounds, Fused-Ring
• Hypnotics and Sedatives
• Nervous System
• Neurotransmitter Agents
• OCT2 Inhibitors
• P-glycoprotein inhibitors
• Psycholeptics
• Psychotropic Drugs
• Tranquilizing Agents

UNII

IHP475989U

CAS number

17617-23-1

Weight

Average: 387.878
Monoisotopic: 387.151368285

Chemical Formula

C₂₁H₂₃ClFN₃O

InChI Key

SAADBVWGJQAEFS-UHFFFAOYSA-N

InChI

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

IUPAC Name

7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

SMILES

CCN(CC)CCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F

Pharmacology

Indication

For short-term and intermittent use in patients with recurring insomnia and poor sleeping habits

Associated Conditions

• Insomnia

Pharmacodynamics

Flurazepam, a benzodiazepine derivative, 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.

Mechanism of action

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.

Target	Actions	Organism
AGABA(A) Receptor	positive allosteric modulator	Humans
AGABA(A) Receptor Benzodiazepine Binding Site	ligand	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Flurazepam hydrochloride is rapidly (30 minutes) absorbed from the gastrointestinal tract

Volume of distribution

Not Available

Protein binding

83%

Metabolism

Flurazepam is rapidly metabolized and is excreted primarily in the urine. Both hydroxyethyl flurazepam (the major metabolite) and N-desalkyl flurazepam are active. The N-desalkyl metabolite is slowly excreted in the urine as the conjugated form

• Flurazepam
  Hydroxyethylflurazepam
• Flurazepam
  N-desalkyl flurazepam

Route of elimination

Flurazepam is rapidly metabolized and is excreted primarily in the urine. Less than 1% of the dose is excreted in the urine as N1-desalkyl-flurazepam.

Half life

The mean apparent half-life of flurazepam is 2.3 hours. The half life of elimination of N1-des-alkyl- flurazepam ranged from 47 to 100 hours

Clearance

Not Available

Toxicity

Coma, confusion, low blood pressure, sleepiness

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Flurazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	The therapeutic efficacy of Flurazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Flurazepam is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Flurazepam is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Flurazepam is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanine	The therapeutic efficacy of Flurazepam can be decreased when used in combination with 6-O-benzylguanine.
7-Deazaguanine	The therapeutic efficacy of Flurazepam can be decreased when used in combination with 7-Deazaguanine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Flurazepam is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Flurazepam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
7,9-Dimethylguanine	The therapeutic efficacy of Flurazepam can be decreased when used in combination with 7,9-Dimethylguanine.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
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Action
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Food Interactions

• Avoid alcohol.
• Take with or without food. The absorption is unaffected by food.

References

Synthesis Reference

Fryer, R. and Sternbach, L.H.; U.S. Patent 3,567,710; March 2, 1971; assigned to Hoffman-La Roche, Inc.

General References

1. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [PubMed:2883820]
2. Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [PubMed:15089115]
3. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451]
4. Rooke KC: The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice. J Int Med Res. 1976;4(5):355-9. [PubMed:18375]
5. Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine]. Arch Fr Pediatr. 1977 Jan;34(1):74-89. [PubMed:851373]
6. Link [Link]

External Links

Human Metabolome Database

HMDB0014828

KEGG Drug

D00329

PubChem Compound

3393

PubChem Substance

46508451

ChemSpider

3276

RxNav

4501

ChEBI

5128

ChEMBL

CHEMBL968

ZINC

ZINC000000537752

Therapeutic Targets Database

DAP000242

PharmGKB

PA449681

PDBe Ligand

FL7

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Flurazepam

ATC Codes

N05CD01 — Flurazepam

• N05CD — Benzodiazepine derivatives
• N05C — HYPNOTICS AND SEDATIVES
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

AHFS Codes

• 28:24.08 — Benzodiazepines

PDB Entries

2yoe

MSDS

Download (50.5 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Insomnia Disorder	1
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia	1

Pharmacoeconomics

Manufacturers

• Valeant pharmaceuticals international
• Halsey drug co inc
• Mutual pharmaceutical co inc
• Mylan pharmaceuticals inc
• Par pharmaceutical inc
• Purepac pharmaceutical co
• Sandoz inc
• Superpharm corp
• Usl pharma inc
• Warner chilcott inc
• Warner chilcott div warner lambert co
• Watson laboratories inc
• West ward pharmaceutical corp

Packagers

• Amerisource Health Services Corp.
• A-S Medication Solutions LLC
• Bryant Ranch Prepack
• Corepharma LLC
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• H.J. Harkins Co. Inc.
• Hl Moore Drug Exchange
• Kaiser Foundation Hospital
• Lake Erie Medical and Surgical Supply
• Legacy Pharmaceuticals Packaging LLC
• Major Pharmaceuticals
• Mylan
• Nucare Pharmaceuticals Inc.
• Par Pharmaceuticals
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Rebel Distributors Corp.
• Remedy Repack
• Southwood Pharmaceuticals
• UDL Laboratories
• Valeant Ltd.
• West-Ward Pharmaceuticals

Dosage forms

Form	Route	Strength
Capsule	Oral	15 mg
Capsule	Oral	15 mg/1
Capsule	Oral	30 mg/1
Capsule	Oral	30 mg
Capsule	Oral
Tablet	Oral

Prices

Unit description	Cost	Unit
Dalmane 30 mg capsule	2.01USD	capsule
Dalmane 15 mg capsule	1.79USD	capsule
Flurazepam HCl 15 mg capsule	0.43USD	capsule
Flurazepam HCl 30 mg capsule	0.4USD	capsule
Flurazepam 30 mg capsule	0.34USD	capsule
Flurazepam 15 mg capsule	0.28USD	capsule
Apo-Flurazepam 30 mg Capsule	0.1USD	capsule
Apo-Flurazepam 15 mg Capsule	0.08USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	190-220	British Patent 1,040,548.
water solubility	500 mg/mL (HCl salt)	Not Available
logP	3.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.01 mg/mL	ALOGPS
logP	3.81	ALOGPS
logP	3.95	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	8.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.91 Å2	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.54 m3·mol-1	ChemAxon
Polarizability	41.22 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9898
Caco-2 permeable	+	0.6115
P-glycoprotein substrate	Substrate	0.8553
P-glycoprotein inhibitor I	Inhibitor	0.9455
P-glycoprotein inhibitor II	Inhibitor	0.6624
Renal organic cation transporter	Inhibitor	0.6523
CYP450 2C9 substrate	Non-substrate	0.7716
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7794
CYP450 1A2 substrate	Inhibitor	0.5194
CYP450 2C9 inhibitor	Non-inhibitor	0.7112
CYP450 2D6 inhibitor	Non-inhibitor	0.5469
CYP450 2C19 inhibitor	Inhibitor	0.5082
CYP450 3A4 inhibitor	Inhibitor	0.6347
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.6231
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.7597
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.5654 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9528
hERG inhibition (predictor II)	Inhibitor	0.7183

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0009000000-c0e65a54e856d501ed8c
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014r-0009000000-5a2839fdce5817956437
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0009000000-ef2f40465f355c7e04c0
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0049000000-aeef40f08b145e9212fb
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0392000000-706f2398b20890152e43

Taxonomy

Description

This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Alpha amino acids and derivatives / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Tertiary carboxylic acid amides / Trialkylamines / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compoundsHydrocarbon derivatives / Carbonyl compounds / Organic oxides / Organochlorides / Organofluorides / Organopnictogen compounds

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Substituents

1,4-benzodiazepine / Alpha-amino acid or derivatives / Halobenzene / Fluorobenzene / Aryl chloride / Monocyclic benzene moiety / Benzenoid / Aryl fluoride / Aryl halide / Tertiary carboxylic acid amideAmino acid or derivatives / Tertiary aliphatic amine / Tertiary amine / Lactam / Carboxamide group / Ketimine / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Azacycle / Carboxylic acid derivative / Organic nitrogen compound / Imine / Organohalogen compound / Organochloride / Organofluoride / Organonitrogen compound / Carbonyl group / Organooxygen compound / Hydrocarbon derivative / Organic oxide / Organopnictogen compound / Organic oxygen compound / Amine / Aromatic heteropolycyclic compound

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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Drug created on June 13, 2005 07:24 / Updated on July 09, 2020 11:59