ContaminantDB: Flurazepam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (46)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:25 UTC

Update Date

2026-05-14 16:46:10 UTC

Accession Number

CHEM002248

Identification

Common Name

Flurazepam

Class

Small Molecule

Description

Flurazepam belongs to the 1,4-benzodiazepines, a subclass of benzodiazepines within the organic compounds. This exogenous organoheterocyclic compound has the formula C21H23ClFN3O and an average molecular weight of 387.88 g/mol. At room temperature, it exists as a solid. It is used as a hypnotic and sedative, with oral exposure recorded. The compound is found in or released from 13 recorded sources. These include drinking water and water supply; food preservation within food, food processing, and cookware; household cleaning and consumer products such as perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites; and electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, radio transmission systems, and electrically stimulated smoking devices. Flurazepam has 20 recorded protein targets, including gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), alpha-5 (GABRA5), beta-1 (GABRB1), beta-3 (GABRB3), gamma-1 (GABRG1), gamma-2 (GABRG2), gamma-3 (GABRG3), and delta (GABRD), among 7 other proteins. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Drug
GABA Modulator
Hypnotic and Sedative
Metabolite
Organic Compound
Organochloride
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Flurazepamum	ChEBI
Insumin	ChEBI
Ro 5-6901	ChEBI
Flurazepam HCL	HMDB
Apo-flurazepam	HMDB
Dalmadorm	HMDB
Flurazepam hydrochloride	HMDB
Hydrochloride, flurazepam	HMDB
Monohydrochloride, flurazepam	HMDB
Allphar brand OF flurazepam monohydrochloride	HMDB
Dalmane	HMDB
Dihydrochloride, flurazepam	HMDB
Dormodor	HMDB
mono-Perchlorate, flurazepam	HMDB
Dolorgiet brand OF flurazepam	HMDB
Flurazepam mono perchlorate	HMDB
Flurazepam monohydrochloride	HMDB
Apo flurazepam	HMDB
Apotex brand OF flurazepam monohydrochloride	HMDB
Flurazepam dihydrochloride	HMDB
Flurazepam mono-perchlorate	HMDB
ICN brand OF flurazepam monohydrochloride	HMDB
Staurodorm	HMDB

Chemical Formula

C₂₁H₂₃ClFN₃O

Average Molecular Mass

387.878 g/mol

Monoisotopic Mass

387.151 g/mol

CAS Registry Number

17617-23-1

IUPAC Name

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

Traditional Name

flurazepam

SMILES

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

InChI Identifier

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

InChI Key

SAADBVWGJQAEFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Halobenzene
Fluorobenzene
Aryl chloride
Monocyclic benzene moiety
Benzenoid
Aryl fluoride
Aryl halide
Tertiary carboxylic acid amide
Amino 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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Flurazepam Action Pathway	SMP0126129	Not Available
Flurazepam Drug Metabolism Action Pathway	SMP0143134	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	190-220°C
Boiling Point	Not Available
Solubility	500 mg/mL (HCl salt)

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-9025000000-1b62ce2349d2235158ef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0009000000-c0e65a54e856d501ed8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014r-0009000000-5a2839fdce5817956437	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0009000000-ef2f40465f355c7e04c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0049000000-aeef40f08b145e9212fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0392000000-706f2398b20890152e43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0019000000-836d40a1a33eaeaaa580	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0293000000-a92d04cc87b08ceb161f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0293000000-9b01e06cd516417f5f40	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0292000000-f326367febc968ad2522	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0292000000-8cd3ddd8803bd6f359a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-5945a4f0ce3357b3e503	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0009000000-b3cb3c42e37c875ac9f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0039000000-1e5e483d7d97a9c53e2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0292000000-3880af53808065081b74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0009000000-548b9f2cbace88e110e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-22a64bb9f4d7b30a7c25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0009000000-fa78c3dd0c1c33184b24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0039000000-b38e1cf8b25b08bffcd6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0009000000-af48919d1fb01be29794	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0219000000-1fb97b7ae98d96c45152	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-2629000000-7417538c28537c7c1bbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-9530000000-a39c1290a2af1bf3ef3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-74869eabef799c5c2e78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-3029000000-d75103db384d94c7c554	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kmu-9352000000-ec693fb8979b23ef4774	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Benzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

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 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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Coma, confusion, low blood pressure, sleepiness

Treatment

General supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. Hypotension and CNS depression may be combated by judicious use of appropriate therapeutic agents. If excitation occurs in patients following Flurazepam overdosage, barbiturates should not be used. Flumazenil, a specific benzodiazepine-receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be useful in situations when an overdose with a benzodiazepine is known or suspected. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB00690

HMDB ID

HMDB0014828

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID