12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.02,6]tetradeca-1(14),3,5,8,10,12-hexaene

• ChemBase编号: 773
• 分子式: C17H12Cl2N4
• 平均质量: 343.20998
• 单一同位素质量: 342.04390176
• SMILES: Clc1cc2c(n3c(nnc3C)CN=C2c2c(Cl)cccc2)cc1
• Canonical SMILES: Clc1ccc2c(c1)C(=NCc1n2c(C)nn1)c1ccccc1Cl
• InChI: InChI=1S/C17H12Cl2N4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3
• InChIKey: JOFWLTCLBGQGBO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,8,10,12-hexaene; 12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene; 12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaene
• IUPAC传统名: triazolam
• 商标名: Alti-Triazolam; Apo-Triazo; Clorazolam; Gen-Triazolam; Halcion; Novidorm; Novo-Triolam; Novodorm; Songar
• 别名: 三唑仑; Triazolam; 8-Chloro-6-[2-chlorophenyl]-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine; DEA No. 2887; Triazolamum [INN-Latin]; Triazolam; 8-Chloro-6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine; 8-Chloro-1-methyl-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine; Clorazolam; D II-18-2; Halcion; Novodorm; Songar; U 33030

登记号

• CAS号: 28911-01-5
• EC号: 249-307-3
• MDL号: MFCD00079623
• PubChem SID: 24900602; 46509147; 160964236
• PubChem CID: 5556
• CHEBI ID: 9674
• ATC码: N05CD05
• CHEMBL: 646
• Chemspider ID: 5355
• DrugBank ID: DB00897
• KEGG ID: D00387
• 美国药典/FDA物质标识码: 1HM943223R
• 维基百科标题: Triazolam
• Medline Plus: a684004

理论计算性质

JChem

• Acid pKa: 18.078356
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 2.864177
• LogD (pH = 7.4): 2.8917372
• Log P: 2.8921
• 摩尔折射率: 103.6838 cm^3
• 极化性: 35.28183 Å^3
• 极化表面积: 43.07 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: 2.94
• LOG S: -4.27
• 溶解度: 1.83e-02 g/l

分子性质

理化性质

• 溶解度: 4.53 mg/L; Methanol
• 外观: Yellow Solid
• 熔点: 209-212°C
• 疏水性(logP): 5.5

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: XZ5472500
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 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: 44% (oral), 53% (sublingual)
• 排泄: Renal
• 半衰期: 1.5-5.5 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV(US)
• 妊娠期药物分类: X (US)
• 相关基因信息: human ... GABRA1(2554)

详细说明

DrugBank - DB00897

• Drug Groups: illicit; approved; withdrawn
• Description: Withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions. This drug continues to be available in the U.S. Internationally, triazolam is a Schedule IV drug under the Convention on Psychotropic Substances.
• Indication: For the short-term treatment of insomnia.
• Pharmacology: A short-acting benzodiazepine used as a hypnotic agent in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries. Triazolam has a shorter half-life than chlordiazepoxide, flurazepam, and prazepam and does not generate active metabolites.
• Toxicity: Symptoms of overdose include drowsiness, slurred speech, motor inco-ordination, coma, and respiratory depression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Small amounts of unmetabolized triazolam appear in the urine.
• Absorption: Bioavailability is 44% (oral) and 53% (sublingual).
• Half Life: 1.5-5.5 hours
• Elimination: Triazolam and its metabolites, principally as conjugated glucuronides, which are presumably inactive, are excreted primarily in the urine. Only small amounts of unmetabolized triazolam appear in the urine. The two primary metabolites accounted for 79.9% of urinary excretion.
• References: 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] ; Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51. [Pubmed] ; Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [Pubmed] ; Veje JO, Andersen K, Gjesing S, Kielgast H: [Prescription of tranquilizers and hypnotics in the municipality of Holbaek] Ugeskr Laeger. 1989 Aug 21;151(34):2134-6. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - T9772

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

Toronto Research Chemicals - T767380

Sedative, hypnotic.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
• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51. Pubmed
• Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. Pubmed
• Veje JO, Andersen K, Gjesing S, Kielgast H: [Prescription of tranquilizers and hypnotics in the municipality of Holbaek] Ugeskr Laeger. 1989 Aug 21;151(34):2134-6. Pubmed
• Lomen, P., et al.: J. Int. Med. Res., 4, 55 (1976)
• Allens, G.S., et al.: J. Int. Med. Res., 6, 343 (1976)
• Pakes, G.E., et al.: Drugs, 22, 81 (1981).