CAS 1172-18-5|CAS 17617-23-1|Dalmadorm|Valdorm|Felison|Flurazepam|Flunox|Somnol|Dalmane|flurazepam|7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one|Noctos...

General Information

Structure

Molecular Formula

C₂₁H₂₃ClFN₃O

Molecular Mass

387.8782232

Exact Mass

387.15136827

Charge

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

InChIKey

SAADBVWGJQAEFS-UHFFFAOYSA-N

Canonic Smiles

CCN(CCN1C(=O)CN=C(c2c1ccc(c2)Cl)c1ccccc1F)CC

Isomeric Smiles

Clc1cc2c(N(CCN(CC)CC)C(=O)CN=C2c2c(F)cccc2)cc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.91958946

LogD (pH = 7.4)

2.6227317

Log P

3.9510489

Molar Refractivity

107.5446

Polarizability

40.716187

Polar Surface Area

35.91

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.81

LOG S

-4.59

Solubility (Water)

1.00e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

Flurazepam HCLFlurazepamFlurazepam DihydrochlorideFelsonBenozil7-Chloro-1-[2-(diethylamino)ethyl]-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one DihydrochlorideSomlanNSC 78559Lunipax7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one HydrochlorideDalmaneID 480Flurazepam HydrochlorideDormodor7-Chloro-1-(2-diethylaminoethyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one DihydrochlorideInsuminRo 5-6901DalmateDalmadorm

IUPAC Traditional name

flurazepam

Brand Name

FlunoxStaurodermSomnolValdormNoctosomFelisonPaxaneInsuminFelmaneDalmadormDalmane

Names and Identifiers

Registration numbers

PubChem SID

PubChem CID

CAS Number

KEGG ID

Unique Ingredient Identifier

Chemspider ID

Wikipedia Title

Medline Plus

ATC CODE

CHEMBL

DrugBank ID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.8

Solubility

500 mg/mL (HCl salt)

Melting Point

79.5°C (175.1°F)

Safety Information

Download link

Product Information

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00690

Drug Groups

illicit; approved

Description

A benzodiazepine derivative used mainly as a hypnotic. [PubChem]

Indication

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

Pharmacology

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.

Toxicity

Coma, confusion, low blood pressure, sleepiness

Affected Organisms

Humans and other mammals

Biotransformation

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

Absorption

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

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

Protein Binding

83%

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.

References

• [Link]

• 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]

• Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [Pubmed]

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed]

• 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]

• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Wikipedia

Flurazepam

TRC

F500800

Flurazepam is used as an sedative, hypnotic. This is a controlled substance (depressant).

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. Pubmed

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed

• Link

• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed

• 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

• Ganjali, M., et al.: Curr. Pharm. Anal., 5, 28 (1965)

• Schwartz, et al.: J. Med. Chem., 11, 770, (1965)

• Armagnac, et al.: Therapie, 26, 439 (1965)

• Sternbach, L.H., et al.: J. Med. Chem., 8, 815 (1965)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC name

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

Synonyms

IUPAC Traditional name

flurazepam

Brand Name

FlunoxStaurodermSomnolValdormNoctosomFelisonPaxaneInsuminFelmaneDalmadormDalmane

Registration numbers

PubChem SID

PubChem CID

CAS Number

KEGG ID

Unique Ingredient Identifier

Chemspider ID

Wikipedia Title

Medline Plus

ATC CODE

CHEMBL

DrugBank ID

Molecule Details

DB00690

Drug Groups

illicit; approved

Description

A benzodiazepine derivative used mainly as a hypnotic. [PubChem]

Indication

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

Pharmacology

Toxicity

Coma, confusion, low blood pressure, sleepiness

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

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

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

Protein Binding

83%

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.

References

• [Link]

• 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]

• Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [Pubmed]

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed]

• 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]

• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Wikipedia

Flurazepam

TRC

F500800

Flurazepam is used as an sedative, hypnotic. This is a controlled substance (depressant).

References

PubChem Literature

From Data Sources

• 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

• Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. Pubmed

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed

• Link

• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed

• 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

• Ganjali, M., et al.: Curr. Pharm. Anal., 5, 28 (1965)

• Schwartz, et al.: J. Med. Chem., 11, 770, (1965)

• Armagnac, et al.: Therapie, 26, 439 (1965)

• Sternbach, L.H., et al.: J. Med. Chem., 8, 815 (1965)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

3.8

Solubility

500 mg/mL (HCl salt)

Melting Point

79.5°C (175.1°F)

Safety Information

Download link

Product Information

Download link

Molecule

ID:572