General Information of Drug (ID: DMZ36RN)

Drug Name
Mazindol
Synonyms
mazindol; Mazanor; Sanorex; Teronac; Mazildene; 22232-71-9; Magrilon; Dimagrir; Mazindolum; Mazindole; Mazindolum [INN-Latin]; Terenac; AN 448; Mazindol [USAN:BAN:INN]; SAH 42548; CCRIS 3152; DEA No 1605; 5-(4-Chlorophenyl)-3,5-dihydro-2H-imidazo[2,1-a]isoindol-5-ol; 5-(4-Chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol; HSDB 3112; SA 42-548; 5-(4-Chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]isoindole; EINECS 244-857-0; S 42548; CHEMBL781; 5-p-Chlorophenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindol-5-ol; BRN 0546547; Diestet; Sanjorex; Solucaps; Teronak; Mazindol Medix Brand; Mazindol Novartis Brand; Mazindol Searle Brand; Mazindol Wyeth Brand; Medix Brand of Mazindol; Novartis Brand of Mazindol; Searle Brand of Mazindol; Wyeth Brand of Mazindol; AN 448;AN448; AN-448; Mazanor (TN); SANOREX (TN); Sanorex (TN); Mazindol (JAN/USP/INN); (+-)-5-(p-Chlorophenyl)-2,5-dihydro-3H-imidazo(2,1-a)isoindol-5-ol; 5-(4-Chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo(2,1-a)isoindole; 5-(4-chlorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol; 5-(p-Chlorophenyl)-2,5-dihydro-3H-imidazo(2,1-a)isoindol-5-ol; 5H-Imidazo(2,1-a)isoindol-5-ol, 5-(4-chlorophenyl)-2,3-dihydro; [3H]mazindol
Indication
Disease Entry ICD 11 Status REF
Obesity 5B81 Approved [1], [2]
Therapeutic Class
Central Nervous System Stimulants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 284.74
Topological Polar Surface Area (xlogp) 2.2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Bioavailability
93% of drug becomes completely available to its intended biological destination(s) [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 10 - 13 hours [4]
Metabolism
The drug is metabolized via the hepatic [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.11695 micromolar/kg/day [6]
Chemical Identifiers
Formula
C16H13ClN2O
IUPAC Name
5-(4-chlorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol
Canonical SMILES
C1CN2C(=N1)C3=CC=CC=C3C2(C4=CC=C(C=C4)Cl)O
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
Cross-matching ID
PubChem CID
4020
ChEBI ID
CHEBI:6702
CAS Number
22232-71-9
DrugBank ID
DB00579
TTD ID
D0H8QL
VARIDT ID
DR00850

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Modulator [7], [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Obesity
ICD Disease Classification 5B81
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Norepinephrine transporter (NET) DTT SLC6A2 7.05E-01 7.02E-03 0.07
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Mazindol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Major Increased risk of hyperpyrexia by the combination of Mazindol and Methylene blue. Acquired methaemoglobinaemia [3A93] [17]
Droxidopa DM5YF4M Moderate Additive hypertensive effects by the combination of Mazindol and Droxidopa. Autonomic nervous system disorder [8D87] [18]
Linezolid DMGFPU2 Major Additive hypertensive effects by the combination of Mazindol and Linezolid. Bacterial infection [1A00-1C4Z] [17]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Mazindol and Ethanol. Cystitis [GC00] [19]
Selegiline DM6034S Major Increased risk of hyperpyrexia by the combination of Mazindol and Selegiline. Depression [6A70-6A7Z] [17]
Isocarboxazid DMAF1NB Major Additive hypertensive effects by the combination of Mazindol and Isocarboxazid. Depression [6A70-6A7Z] [17]
Tranylcypromine DMGB5RE Major Additive hypertensive effects by the combination of Mazindol and Tranylcypromine. Depression [6A70-6A7Z] [20]
Phenelzine DMHIDUE Major Increased risk of hyperpyrexia by the combination of Mazindol and Phenelzine. Depression [6A70-6A7Z] [17]
Esketamine DMVU687 Major Additive hypertensive effects by the combination of Mazindol and Esketamine. Depression [6A70-6A7Z] [21]
Procarbazine DMIK367 Major Additive hypertensive effects by the combination of Mazindol and Procarbazine. Hodgkin lymphoma [2B30] [17]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Mazindol and Polyethylene glycol. Irritable bowel syndrome [DD91] [22]
Promethazine DM6I5GR Moderate Antagonize the effect of Mazindol when combined with Promethazine. Nausea/vomiting [MD90] [23]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Mazindol and Bupropion. Nicotine use disorder [6C4A] [24]
Safinamide DM0YWJC Moderate Decreased metabolism of Mazindol caused by Safinamide mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [25]
Rasagiline DM3WKQ4 Moderate Additive hypertensive effects by the combination of Mazindol and Rasagiline. Parkinsonism [8A00] [17]
Mesoridazine DM2ZGAN Moderate Antagonize the effect of Mazindol when combined with Mesoridazine. Schizophrenia [6A20] [26]
Thioridazine DM35M8J Moderate Antagonize the effect of Mazindol when combined with Thioridazine. Schizophrenia [6A20] [26]
Perphenazine DMA4MRX Moderate Antagonize the effect of Mazindol when combined with Perphenazine. Schizophrenia [6A20] [23]
Trifluoperazine DMKBYWI Moderate Antagonize the effect of Mazindol when combined with Trifluoperazine. Schizophrenia [6A20] [23]
⏷ Show the Full List of 19 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4797).
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3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Binding of [3H]mazindol to cardiac norepinephrine transporters: kinetic and equilibrium studies. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):9-16.
8 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
9 Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107.
10 Treatment of comorbid pain with serotonin norepinephrine reuptake inhibitors. CNS Spectr. 2008 Jul;13(7 Suppl 11):22-6.
11 Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
12 Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81.
13 Clinically relevant drug interactions with new generation antidepressants and antipsychotics. Ther Umsch. 2009 Jun;66(6):485-92.
14 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
15 Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90.
16 Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today. 2007 Jan;12(1-2):34-42.
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23 Achor MB, Extein I "Diet aids, mania, and affective illness" Am J Psychiatry 138 (1981): 392. [PMID: 7468847]
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26 Lake CR "Manic psychosis after coffee and phenylpropanolamine." Biol Psychiatry 30 (1991): 401-4. [PMID: 1912131]