Identification
- Summary
Flurazepam is a long-acting benzodiazepine with a rapid onset of action that is commonly used to treat insomnia.
- Brand Names
- Dalmane
- Generic Name
- Flurazepam
- DrugBank Accession Number
- DB00690
- Background
A benzodiazepine derivative used mainly as a hypnotic.
- Type
- Small Molecule
- Groups
- Approved, Illicit, Investigational
- Structure
Structure for Flurazepam (DB00690)
- Weight
- Average: 387.878
Monoisotopic: 387.151368285 - Chemical Formula
- C21H23ClFN3O
- Synonyms
- Flurazepam
- Flurazépam
- Flurazepamum
- External IDs
- ID 480
- Ro 5-6901
Pharmacology
- Indication
For short-term and intermittent use in patients with recurring insomnia and poor sleeping habits
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Insomnia •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - 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
Hover over products below to view reaction partners
- 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
- Adverse Effects
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Coma, confusion, low blood pressure, sleepiness
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Flurazepam is combined with 1,2-Benzodiazepine. Abacavir Flurazepam may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Flurazepam can be increased when it is combined with Abametapir. Abatacept The metabolism of Flurazepam can be increased when combined with Abatacept. Aceclofenac Aceclofenac may decrease the excretion rate of Flurazepam which could result in a higher serum level. - Food Interactions
- Avoid alcohol.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Flurazepam hydrochloride 7C4JH842IJ 36105-20-1 PUGVROXLRUQCAF-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Dalmadorm (Meda) / Dalmadorm medium (Meda) / Felison (SIT) / Flunox (Teofarma) / Insumin / Sompan (I.C.N.) / Valdorm (Valeas)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dalmane Capsule 15 mg Oral Valeant Canada Lp Valeant Canada S.E.C. 1971-12-31 2016-07-08 Canada 
Dalmane Capsule 30 mg Oral Valeant Canada Lp Valeant Canada S.E.C. 1971-12-31 2016-07-08 Canada Flurazepam Capsule 30 mg Oral Aa Pharma Inc 1982-12-31 Not applicable Canada Flurazepam Capsule 15 mg Oral Aa Pharma Inc 1982-12-31 Not applicable Canada Flurazepam 15 Capsule 15 mg Oral Pro Doc Limitee 1982-12-31 2018-04-18 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bio-flurazepam Capsule 30 mg Oral Biomed Pharma 2004-04-23 2022-07-19 Canada Bio-flurazepam Capsule 15 mg Oral Biomed Pharma 2004-04-23 2022-07-19 Canada Flurazepam Capsule 15 mg/1 Oral Golden State Medical Supply 1986-12-08 2017-01-02 US 
Flurazepam Capsule 30 mg/1 Oral A S Medication Solutions 1986-12-08 Not applicable US 
Flurazepam Capsule 15 mg/1 Oral bryant ranch prepack 1986-12-08 2014-01-01 US 
Categories
- ATC Codes
- N05CD01 — Flurazepam
- Drug 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
- Chemical TaxonomyProvided by Classyfire
- 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 compounds show 6 more
- Substituents
- 1,4-benzodiazepine / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- IHP475989U
- CAS number
- 17617-23-1
- 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
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
- 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. [Article]
- Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [Article]
- Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Article]
- 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. [Article]
- Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine]. Arch Fr Pediatr. 1977 Jan;34(1):74-89. [Article]
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0014828
- KEGG Drug
- D00329
- PubChem Compound
- 3393
- PubChem Substance
- 46508451
- ChemSpider
- 3276
- 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
- PDB Entries
- 2yoe
- MSDS
- Download (50.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 1 Completed Treatment Insomnia Disorder 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 Tablet, film coated Oral 30 mg/1 Capsule Oral Capsule Oral 15 mg/1 Capsule Oral 30 mg/1 Capsule Oral 30 mg Capsule Oral 15 mg Tablet Oral 27.42 mg Capsule Oral 15 mg / cap Capsule Oral 30 mg / cap Tablet Oral 15 mg Tablet Oral 30 mg - 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 41.2 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 194.2482869 predictedDarkChem Lite v0.1.0 [M-H]- 189.62123 predictedDeepCCS 1.0 (2019) [M+H]+ 194.5635869 predictedDarkChem Lite v0.1.0 [M+H]+ 192.05421 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.3718869 predictedDarkChem Lite v0.1.0 [M+Na]+ 199.52672 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- Curator comments
- The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- Curator comments
- Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Capello S, Henderson L, DeGrazia F, Liberato D, Garland W, Town C: The effect of the cytochrome P-450 suicide inactivator, 1-aminobenzotriazole, on the in vivo metabolism and pharmacologic activity of flurazepam. Drug Metab Dispos. 1990 Mar-Apr;18(2):190-6. [Article]
- Linder CD, Renaud NA, Hutzler JM: Is 1-aminobenzotriazole an appropriate in vitro tool as a nonspecific cytochrome P450 inactivator? Drug Metab Dispos. 2009 Jan;37(1):10-3. doi: 10.1124/dmd.108.024075. Epub 2008 Oct 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Capello S, Henderson L, DeGrazia F, Liberato D, Garland W, Town C: The effect of the cytochrome P-450 suicide inactivator, 1-aminobenzotriazole, on the in vivo metabolism and pharmacologic activity of flurazepam. Drug Metab Dispos. 1990 Mar-Apr;18(2):190-6. [Article]
- Linder CD, Renaud NA, Hutzler JM: Is 1-aminobenzotriazole an appropriate in vitro tool as a nonspecific cytochrome P450 inactivator? Drug Metab Dispos. 2009 Jan;37(1):10-3. doi: 10.1124/dmd.108.024075. Epub 2008 Oct 20. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Zolk O, Solbach TF, Konig J, Fromm MF: Functional characterization of the human organic cation transporter 2 variant p.270Ala>Ser. Drug Metab Dispos. 2009 Jun;37(6):1312-8. doi: 10.1124/dmd.108.023762. Epub 2009 Feb 27. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55