7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase编号: 720
• 分子式: C15H11ClN2O2
• 平均质量: 286.71304
• 单一同位素质量: 286.05090528
• SMILES: Clc1cc2C(=NC(O)C(=O)Nc2cc1)c1ccccc1
• Canonical SMILES: O=C1Nc2ccc(cc2C(=NC1O)c1ccccc1)Cl
• InChI: InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
• InChIKey: ADIMAYPTOBDMTL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC传统名: oxazepam
• 商标名: Adumbran; Ansioxacepam; Anxiolit; Aplakil; Astress; Azutranquil; Bonare; Drimuel; Droxacepam; Durazepam; Enidrel; Hi-Long; Isodin; Lederpam; Limbial; Murelax; Nesontil; Noctazepam; Notaral; Oxa-puren; Oxanid; Pacienx; Praxiten; Propax; Psiquiwas; QUEN; Quilibrex; Rondar; Sedigoa; Serax; Serenal; Serenid; Serenid-D; Serepax; Seresta; Serpax; Sigacalm; Sobril; Tacepam; Tazepam; Uskan; Vaben; Wy-3498 stic; Zaxopam
• 别名: 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Adumbran; Anxiolit; Durazepam; N-Desmethyltemazepam; NSC 169448; Nesontil; Noctazepam; Serepax; Seresta; Wy 3498; Zaxopam; d-Oxazepam hemisuccinate; Oxozepam; Oxazipam; Oxazepam; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-1,4(2H)-benzodiazepin-2-one; Oxazepam

登记号

• CAS号: 604-75-1
• EC号: 210-076-9
• MDL号: MFCD00057903
• PubChem SID: 160964183; 46506031; 24898014
• PubChem CID: 4616
• CHEBI ID: 7823
• ATC码: N05BA04
• CHEMBL: 568
• Chemspider ID: 4455
• DrugBank ID: DB00842
• KEGG ID: D00464
• 医学主题词(MeSH): Oxazepam
• 美国药典/FDA物质标识码: 6GOW6DWN2A
• 维基百科标题: Oxazepam

理论计算性质

JChem

• Acid pKa: 10.607201
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.9232774
• LogD (pH = 7.4): 2.9230137
• Log P: 2.9232807
• 摩尔折射率: 77.8944 cm^3
• 极化性: 29.113512 Å^3
• 极化表面积: 61.69 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.01
• LOG S: -3.51
• 溶解度: 8.81e-02 g/l

分子性质

理化性质

• 溶解度: 179 mg L^-1 in water; 179 mg/L
• 熔点: 205 - 206°C
• 分配系数: 2.216
• 疏水性(logP): 2.8
• pKa: 10.939
• pKb: 3.058

安全信息

• RTECS编号: DF1400000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40; R40
• 安全公开号: 36/37; S36/37
• GHS危险品标识: GHS health hazard; GHS08
• GHS警示词: WARNING; Warning
• GHS危险声明: 351; H351
• GHS警示性声明: 281; P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 毒品管制信息: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 给药途径: Oral
• 生物利用度: 95.5%
• 排泄: Renal
• 半衰期: 5-15 h
• 代谢: Hepatic
• 法定药品分级: S4 (Australia); Schedule IV (US)
• 相关基因信息: human ... GABRA1(2554)

详细说明

DrugBank - DB00842

• Drug Groups: approved
• Description: Oxazepam is an intermediate-acting benzodiazepine used to treat alcohol withdrawal and anxiety disorders.
• Indication: For the treatment of anxiety disorders and alcohol withdrawal.
• Pharmacology: Oxazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
• Toxicity: Symptoms of overdose include confusion, drowsiness, and lethargy.
• Affected Organisms: Humans and other mammals
• Biotransformation: No active metabolites. Metabolized via conjugation prior to elimination.
• Absorption: Well absorbed from the gastrointestinal tract following oral administration. Time to peak concentration = 2-4 hours. Onset of action is slow, > 3 hours, following oral administration.
• Half Life: 5-15 hours
• Protein Binding: 80-99%
• Elimination: This product has a single, major inactive metabolite in man, a glucuronide excreted in the urine.
• References: Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. [Pubmed] ; Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [Pubmed] ; Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. [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

Sigma Aldrich - O5254

Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

Toronto Research Chemicals - O845700

Anxiolytic; muscle relaxant (skeletal); anticonvulsant; ligand for the GABAA receptor benzodiazepine modulatory site. Controlled substance (depressant).

参考文献

• Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. Pubmed
• Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. Pubmed
• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. Pubmed
• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Sisenwine, et al.: Arzneim. Forsch., 22, 682 (1971)
• Shearer, C.M., et al.: Anal. Profiles Drug Subs., 3, 441 (1971)
• Greenblatt, D.J., et al.: Clin. Pharmacokinet., 6, 89 (1971)