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

• ChemBase编号: 572
• 分子式: C21H23ClFN3O
• 平均质量: 387.8782232
• 单一同位素质量: 387.15136827
• 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

名称和登记号

名称

• IUPAC标准名: 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC传统名: flurazepam
• 商标名: Dalmane; Felison; Felmane; Flunox; Insumin; Noctosom; Paxane; Somnol; Stauroderm; Valdorm; Dalmadorm
• 别名: 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

登记号

• CAS号: 1172-18-5; 17617-23-1
• PubChem SID: 160964035; 46508451
• PubChem CID: 3393
• ATC码: N05CD01
• CHEMBL: 968
• Chemspider ID: 3276
• DrugBank ID: DB00690
• KEGG ID: D00329
• 美国药典/FDA物质标识码: IHP475989U
• 维基百科标题: Flurazepam
• Medline Plus: a682051

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.91958946
• LogD (pH = 7.4): 2.6227317
• Log P: 3.9510489
• 摩尔折射率: 107.5446 cm^3
• 极化性: 40.716187 Å^3
• 极化表面积: 35.91 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.81
• LOG S: -4.59
• 溶解度: 1.00e-02 g/l

分子性质

理化性质

• 溶解度: 500 mg/mL (HCl salt)
• 熔点: 79.5°C (175.1°F)
• 疏水性(logP): 3.8

药理学性质

• 给药途径: Oral
• 生物利用度: 83%
• 排泄: Renal
• 半衰期: 40–250 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV (US)
• 妊娠期药物分类: X (Contraindicated in pregnancy)

详细说明

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

Toronto Research Chemicals - F500800

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

参考文献

• 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)