5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol

• ChemBase编号: 461
• 分子式: C16H13ClN2O
• 平均质量: 284.74022
• 单一同位素质量: 284.07164073
• SMILES: Clc1ccc(C2(O)N3C(=NCC3)c3c2cccc3)cc1
• Canonical SMILES: Clc1ccc(cc1)C1(O)c2ccccc2C2=NCCN12
• InChI: InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2
• InChIKey: ZPXSCAKFGYXMGA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol
• IUPAC传统名: mazindol
• 商标名: DEA No. 1605; Dimagrir; Magrilon; Mazanor; Mazildene; Mazindol [USAN:BAN:INN]; Mazindolum [INN-Latin]; Sanorex; Terenac; Teronac
• 别名: Mazindol; 5-(4-Chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol; Mazindol

登记号

• CAS号: 22232-71-9
• EC号: 244-857-0
• MDL号: MFCD00864480
• PubChem SID: 24896596; 46509094; 160963924
• PubChem CID: 4020
• ATC码: A08AA05
• CHEMBL: 781
• Chemspider ID: 3880
• DrugBank ID: DB00579
• KEGG ID: D00367
• 美国药典/FDA物质标识码: C56709M5NH
• 维基百科标题: Mazindol

理论计算性质

JChem

• 可自由旋转的化学键: 1
• 里宾斯基五规则: true
• Acid pKa: 11.61332
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.4254982
• LogD (pH = 7.4): 3.435128
• Log P: 3.435279
• 摩尔折射率: 79.4221 cm^3
• 极化性: 30.142792 Å^3
• 极化表面积: 35.83 Å^2

ALOGPS 2.1

• 溶解度: 1.39e-01 g/l
• Log P: 2.64
• LOG S: -3.31

分子性质

理化性质

• 溶解度: DMSO: soluble10 mg/mL
• 外观: white powder
• 疏水性(logP): 3.7

安全信息

• RTECS编号: NI2975000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 23/24/25
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H311-H331
• GHS警示性声明: P261-P264-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 毒品管制信息: USDEA Schedule IV; Home Office Schedule 3; 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: 93%
• 排泄: Renal
• 半衰期: 10-13 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV (International); Schedule IV (US)
• 相关基因信息: human ... SLC6A2(6530), SLC6A3(6531), SLC6A4(6532)rat ... Htr1a(24473), Htr2a(29595), Slc6a3(24898), Slc6a4(25553)

产品相关信息

• 纯度: ≥98% (TLC)

详细说明

DrugBank - DB00579

• Drug Groups: approved
• Description: Tricyclic anorexigenic agent unrelated to and less toxic than amphetamine, but with some similar side effects. It inhibits uptake of catecholamines and blocks the binding of cocaine to the dopamine uptake transporter. [PubChem]
• Indication: Used in short-term (a few weeks) treatment of exogenous obesity in conjunction with a regimen of weight reduction based on caloric restriction, exercise, and behavior modification in patients with a body mass index of 30 kg of body weight per height in meters squared (kg/m^2) or in patients with a body mass index of 27 kg/m^2 in the presence of risk factors such as hypertension, diabetes, or hyperlipidemia.
• Pharmacology: Mazindol is a sympathomimetic amine, which is similar to an amphetamine. Mazindol stimulates the central nervous system (nerves and brain), which increases your heart rate and blood pressure and decreases your appetite. Sympathomimetic appetite suppressants are used in the short-term treatment of obesity. Their appetite-reducing effect tends to decrease after a few weeks. Because of this, these medicines are useful only during the first few weeks of a weight-loss program.
• Toxicity: Symptoms of a mazindol overdose include restlessness, tremor, rapid breathing, confusion, hallucinations, panic, aggressiveness, nausea, vomiting, diarrhea, an irregular heartbeat, and seizures.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 10-13 hours
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - M2017

Biochem/physiol Actions
Anorectic agent; inhibits the dopamine, norepinephrine and serotonin transporters with Kis of 27.6 nM, 3.2 nM, and 153 nM, respectively.