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

• ChemBase ID: 461
• Molecular Formular: C16H13ClN2O
• Molecular Mass: 284.74022
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol
• IUPAC Traditional name: mazindol
• Brand Name: DEA No. 1605; Dimagrir; Magrilon; Mazanor; Mazildene; Mazindol [USAN:BAN:INN]; Mazindolum [INN-Latin]; Sanorex; Terenac; Teronac
• Synonyms: Mazindol; 5-(4-Chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol; Mazindol

Database IDs

• CAS Number: 22232-71-9
• EC Number: 244-857-0
• MDL Number: MFCD00864480
• PubChem SID: 24896596; 160963924; 46509094
• PubChem CID: 4020
• ATC CODE: A08AA05
• CHEMBL: 781
• Chemspider ID: 3880
• DrugBank ID: DB00579
• KEGG ID: D00367
• Unique Ingredient Identifier: C56709M5NH
• Wikipedia Title: Mazindol

CALCULATED PROPERTIES

JChem

• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 11.61332
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4254982
• LogD (pH = 7.4): 3.435128
• Log P: 3.435279
• Molar Refractivity: 79.4221 cm^3
• Polarizability: 30.142792 Å^3
• Polar Surface Area: 35.83 Å^2

ALOGPS 2.1

• Solubility (Water): 1.39e-01 g/l
• Log P: 2.64
• LOG S: -3.31

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL
• Apperance: white powder
• Hydrophobicity(logP): 3.7

Safety Information

• RTECS: NI2975000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H311-H331
• GHS Precautionary statements: P261-P264-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 93%
• Excretion: Renal
• Half Life: 10-13 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV (International); Schedule IV (US)
• Gene Information: human ... SLC6A2(6530), SLC6A3(6531), SLC6A4(6532)rat ... Htr1a(24473), Htr2a(29595), Slc6a3(24898), Slc6a4(25553)

Product Information

• Purity: ≥98% (TLC)

DETAILS

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.