7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase编号: 1342
• 分子式: C14H10BrN3O
• 平均质量: 316.1527
• 单一同位素质量: 315.00072396
• SMILES: Brc1cc2c(NC(=O)CN=C2c2ncccc2)cc1
• Canonical SMILES: O=C1CN=C(c2c(N1)ccc(c2)Br)c1ccccn1
• InChI: InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)
• InChIKey: VMIYHDSEFNYJSL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC传统名: bromazepam
• 商标名: Apo-Bromazepam; Calmepam; Compedium; Compendium; Creosedin; Durazanil; Gen-Bromazepam; Lectopam; Lekotam; Lexaurin; Lexilium; Lexomil; Lexotan; Lexotanil; Normoc; Novo-bromazepam; Nu-Bromazepam; Ultramidol; Somalium; Lexotan, Lexotanil
• 别名: 7-溴-5-(2-吡啶基)-3H-1,4-苯并二氮杂卓-2(1H)-酮; 溴西泮; Bromazepam; 7-Bromo-1,3-dihydro-5-(2-pyridinyl)-2H-1,4-benzodiazepin-2-one; Compendium; Creosedin; Durazanil; Lexilium; Lexomil; Lexotan; Lexotanil; NSC 140669; Normoc; Ro 5-3350; Bromazepam; 7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiaxepin-2(1H)-one; 7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiazepin-2(1H)-one; Bromazepamum [inn-latin]

登记号

• CAS号: 1812-30-2
• EC号: 217-322-4; 200-659-6
• MDL号: MFCD00057902
• PubChem SID: 160964802; 46505694; 24891754
• PubChem CID: 2441
• ATC码: N05BA08
• CHEMBL: 277062
• Chemspider ID: 2347
• DrugBank ID: DB01558
• KEGG ID: D01245
• 美国药典/FDA物质标识码: X015L14V0O
• 维基百科标题: Bromazepam

理论计算性质

JChem

• Acid pKa: 12.238634
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.5442781
• LogD (pH = 7.4): 2.5448925
• Log P: 2.5449064
• 摩尔折射率: 76.9851 cm^3
• 极化性: 28.506214 Å^3
• 极化表面积: 54.35 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: 2.09
• LOG S: -3.9
• 溶解度: 3.99e-02 g/l

分子性质

理化性质

• 外观: Crystalline Solid
• 熔点: 205-210°C (dec.)
• 闪点: 11 °C; 51.8 °F
• 疏水性(logP): 2.05 [SANGSTER (1994)]

安全信息

• RTECS编号: DE9800000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1230
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25; 22-36/37/38
• 安全公开号: 26-36; 7-16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H225-H301-H311-H331-H370; H302-H315-H319-H335
• GHS警示性声明: P210-P260-P280-P301 + P310-P311; P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2
• 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
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 生物利用度: 84%
• 排泄: Renal
• 半衰期: 12-20 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV(US)
• 妊娠期药物分类: D (USA)

产品相关信息

• 纯度: ≥98%
• 浓度: 1.0 mg/mL±5% in methanol
• 级别: analytical standard, for drug analysis; drug standard

详细说明

DrugBank - DB01558

• Drug Groups: illicit; approved
• Description: One of the benzodiazepines that is used in the treatment of anxiety disorders. [PubChem] It is a Schedule IV drug in the U.S. and Canada and under the Convention on Psychotropic Substances.
• Indication: For the short-term treatment of insomnia, short-term treatment of anxiety or panic attacks, if a benzodiazepine is required, and the alleviation of the symptoms of alcohol- and opiate-withdrawal.
• Pharmacology: Bromazepam is a lipophilic, long-acting benzodiazepine and with sedative, hypnotic, anxiolytic and skeletal muscle relaxant properties. It does not possess any antidepressant qualities. Bromazepam shares with other benzodiazepines the risk of abuse, misuse, psychological and/or physical dependence. According to many psychiatric experts Bromazepam has a greater abuse potential than other benzodiazepines because of fast resorption and rapid onset of action.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatically, via oxidative pathways (via an enzyme belonging to the Cytochrome P450 family of enzymes).
• Absorption: Bioavailability is 84% following oral administration.
• Half Life: 10-20 hours
• References: Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. [Pubmed] ; van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. [Pubmed] ; Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - B4144

Biochem/physiol Actions
抗焦虑药

Toronto Research Chemicals - B678500

Controlled substance (depressant). Anxiolytic.

参考文献

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. Pubmed
• van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. Pubmed
• Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. Pubmed
• Schwartz, M.A., et al.: J. Pharm. Sci., 62, 1776 (1973)
• Chalmers, P., et al.: Anesthesia, 39, 370 (1973)
• Hassan, M.M., et al.: Anal. Profiles Drug Subs., 16, 1 (1973)