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17617-23-1 molecular structure
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7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

ChemBase ID: 572
Molecular Formular: C21H23ClFN3O
Molecular Mass: 387.8782232
Monoisotopic Mass: 387.15136827
SMILES and InChIs

SMILES:
Clc1cc2c(N(CCN(CC)CC)C(=O)CN=C2c2c(F)cccc2)cc1
Canonical SMILES:
CCN(CCN1C(=O)CN=C(c2c1ccc(c2)Cl)c1ccccc1F)CC
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

Cite this record

CBID:572 http://www.chembase.cn/molecule-572.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
IUPAC Traditional name
flurazepam
Brand Name
Dalmane
Felison
Felmane
Flunox
Insumin
Noctosom
Paxane
Somnol
Stauroderm
Valdorm
Dalmadorm
Synonyms
Flurazepam HCL
Flurazepam
7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one Hydrochloride
7-Chloro-1-(2-diethylaminoethyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one Dihydrochloride
7-Chloro-1-[2-(diethylamino)ethyl]-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one Dihydrochloride
Benozil
Dalmadorm
Dalmane
Dalmate
Dormodor
Felson
Flurazepam Hydrochloride
ID 480
Insumin
Lunipax
NSC 78559
Ro 5-6901
Somlan
Flurazepam Dihydrochloride
CAS Number
17617-23-1
1172-18-5
PubChem SID
46508451
160964035
PubChem CID
3393
ATC CODE
N05CD01
CHEMBL
968
Chemspider ID
3276
DrugBank ID
DB00690
KEGG ID
D00329
Unique Ingredient Identifier
IHP475989U
Wikipedia Title
Flurazepam
Medline Plus
a682051

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
F500800 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.91958946  LogD (pH = 7.4) 2.6227317 
Log P 3.9510489  Molar Refractivity 107.5446 cm3
Polarizability 40.716187 Å3 Polar Surface Area 35.91 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.81  LOG S -4.59 
Solubility (Water) 1.00e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
500 mg/mL (HCl salt) expand Show data source
Melting Point
79.5°C (175.1°F) expand Show data source
Hydrophobicity(logP)
3.8 expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
83% expand Show data source
Excretion
Renal expand Show data source
Half Life
40–250 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Schedule IV (US) expand Show data source
Pregnancy Category
X (Contraindicated in pregnancy) expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00690 external link
Item Information
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
Toronto Research Chemicals - F500800 external link
Flurazepam is used as an sedative, hypnotic. This is a controlled substance (depressant).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • •  Link
  • • Sternbach, L.H., et al.: J. Med. Chem., 8, 815 (1965)
  • • Schwartz, et al.: J. Med. Chem., 11, 770, (1965)
  • • Armagnac, et al.: Therapie, 26, 439 (1965)
  • • Ganjali, M., et al.: Curr. Pharm. Anal., 5, 28 (1965)
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PATENTS

PATENTS

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