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Details

Stereochemistry RACEMIC
Molecular Formula C16H13ClN2O
Molecular Weight 284.74
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAZINDOL

SMILES

OC1(N2CCN=C2C3=CC=CC=C13)C4=CC=C(Cl)C=C4

InChI

InChIKey=ZPXSCAKFGYXMGA-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Mazindol is an amphetamine-like medicine which was developed by Sandoz in 1967 and approved by FDA for the treatment of obesity and Duchenne muscular dystrophy under the names Sanorex and Mazanor. The exact mechanism of action is unknown, but possibly involves the stimulation of beta-adrenergic receptors and inhibition of monoamine reuptake. Both Sanorex and Mazanor were withdrawn from the market by reason other than safety. NLS Pharma now is developing mazindol for Attention Hyperactivity Disorder in adults (phase II).

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SANOREX

Approved Use

Unknown

Launch Date

1.08863996E11
Primary
SANOREX

Approved Use

Treatment of Duchenne muscular dystrophy.

Launch Date

5.24188811E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.09 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MAZINDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
35.63 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MAZINDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.66 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MAZINDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Pharmacological analysis of a new anorexic substance: 5-hydroxy-5(4'-chlorophenyl)-2, 3-dihydro-5H-imidazo-(2, 1-a) isoindole (Mazindol).
1975 Apr
Short-term and long-term clinical evaluation of a non-amphetaminic anorexiant (mazindol) in the treatment of obesity.
1976
Serial echocardiographic and clinical evaluation of valvular regurgitation before, during, and after treatment with fenfluramine or dexfenfluramine and mazindol or phentermine.
1999 Jul
Pharmaceutical cost savings of treating obesity with weight loss medications.
1999 Nov
Decreased densities of dopamine and serotonin transporters and of vesicular monoamine transporter 2 in severely kainic acid lesioned subregions of the striatum.
2001
Anticocaine catalytic antibodies have no affinity for RTI compounds: implications for treatment.
2001 Aug
Long-term pharmacotherapy of obesity 2000: a review of efficacy and safety.
2001 Aug 13-27
Dopamine transporter binding in the rat striatum is increased by gestational, perinatal, and adolescent exposure to heptachlor.
2001 Dec
6-Hydroxydopamine-lesioning of the nigrostriatal pathway in rats alters basal ganglia mRNA for copper, zinc- and manganese-superoxide dismutase, but not glutathione peroxidase.
2001 Dec 13
Expression of striatal preprotachykinin mRNA in symptomatic and asymptomatic 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-exposed monkeys is related to parkinsonian motor signs.
2001 Jul 1
Role of 5-HT(2a) and 5-HT(2B/2C) receptors in the behavioral interactions between serotonin and catecholamine reuptake inhibitors.
2001 Mar
The role of conserved tryptophan and acidic residues in the human dopamine transporter as characterized by site-directed mutagenesis.
2001 May
[Monoaminergic anorectic agents].
2001 Nov
Effects of dopaminergic and cholinergic interactions on rat behavior.
2001 Oct 5
Unilateral infusion of a dopamine transporter antisense into the substantia nigra protects against MDMA-induced serotonergic deficits in the ipsilateral striatum.
2002
Dopamine transporter mutants with cocaine resistance and normal dopamine uptake provide targets for cocaine antagonism.
2002 Apr
Pharmacological treatment of cocaine dependence: a systematic review.
2002 Aug
5-HT3 receptor antagonist MDL 72222 attenuates cocaine- and mazindol-, but not methylphenidate-induced neurochemical and behavioral effects in the rat.
2002 Feb
Caffeine's neuroprotection against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine toxicity shows no tolerance to chronic caffeine administration in mice.
2002 Mar 29
Benzo- and cyclohexanomazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter.
2002 Sep 12
Noradrenergic modulation of ephedrine-induced hypophagia.
2003 Apr
Obesity.
2003 Dec
Treatment of obesity: an update on anti-obesity medications.
2003 Feb
Effects of green tea polyphenols on dopamine uptake and on MPP+ -induced dopamine neuron injury.
2003 Jan 17
Assessment of mazindane, a pro-drug form of mazindol, in assays used to define cocaine treatment agents.
2003 Jan 5
Apparent opposite effects of tetrabenazine and reserpine on the toxic effects of 1-methyl-4-phenylpyridinium or 6-hydroxydopamine on nigro-striatal dopaminergic neurons.
2003 Nov 7
Dopamine transporter as target for drug development of cocaine dependence medications.
2003 Oct 31
Dopamine transmission in DYT1 dystonia.
2004
Differential effects of prolonged high frequency stimulation and of excitotoxic lesion of the subthalamic nucleus on dopamine denervation-induced cellular defects in the rat striatum and globus pallidus.
2004 Dec
Chronic intoxication with 3-nitropropionic acid in rats induces the loss of striatal dopamine terminals without affecting nigral cell viability.
2004 Jan 16
Binding of [3H]mazindol to cardiac norepinephrine transporters: kinetic and equilibrium studies.
2004 Jul
Obesity.
2004 Jun
[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry].
2004 May
Sensitivity to oxidative stress in DJ-1-deficient dopamine neurons: an ES- derived cell model of primary Parkinsonism.
2004 Nov
Low dose pramipexole is neuroprotective in the MPTP mouse model of Parkinson's disease, and downregulates the dopamine transporter via the D3 receptor.
2004 Oct 11
Hypersomnia.
2005
Diabesity: are weight loss medications effective?
2005
Perinatal heptachlor exposure increases expression of presynaptic dopaminergic markers in mouse striatum.
2005 Aug
Endothelin-1 inhibits the neuronal norepinephrine transporter in hearts of male rats.
2005 Aug 1
The interaction of methylphenidate and benztropine with the dopamine transporter is different than other substrates and ligands.
2005 Aug 1
Pharmacotherapy for weight loss in adults with type 2 diabetes mellitus.
2005 Jan 25
Inhibiting BDNF expression by antisense oligonucleotide infusion causes loss of nigral dopaminergic neurons.
2005 Mar
Mechanism of 1-methyl-4-phenylpyridinium-induced dopamine release from PC12 cells.
2005 May
Effects of monoamine reuptake inhibitors on wet-dog shakes mediated by 5-HT2A receptors in ACTH-treated rats.
2005 May
A reliable model of intravenous MDMA self-administration in naïve mice.
2006 Jan
Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants.
2006 Jan 27
Patents

Sample Use Guides

In Vivo Use Guide
Sources: DOI: 10.1604/9780440235378, Catalano J., 'The Women's Pharmacy: An Essential Guide to What Women Should Know About Prescription Drugs' (2008), p.218, Retrieved from https://books.google.es/books?id=WueSNTyQq6sC&dq
The usual dose is 1 mg three times a day an hour before meals or 2 mg once a day an our before lunch.
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/9282933
C6 glioma cells stably expressing hDAT were treated with 10 nM of mazindol to test its binding to the dopamine transporter.
Name Type Language
MAZINDOL
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
TERENAC
Brand Name English
AN-448
Code English
(±)-5-(P-CHLOROPHENYL)-2,5-DIHYDRO-3H-IMIDAZO(2,1-A)ISOINDOL-5-OL
Common Name English
3H-IMIDAZO(2,1-A)ISOINDOL-5-OL, 5-(4-CHLOROPHENYL)-2,5-DIHYDRO-, (±)-
Systematic Name English
MAZINDOL [MART.]
Common Name English
MAZINDOL CIV
USP-RS  
Common Name English
MAZINDOL [MI]
Common Name English
mazindol [INN]
Common Name English
SANOREX
Brand Name English
MAZINDOL [VANDF]
Common Name English
MAZINDOL [JAN]
Common Name English
MAZINDOL [ORANGE BOOK]
Common Name English
MAZINDOL [HSDB]
Common Name English
Mazindol [WHO-DD]
Common Name English
MAGRILON
Brand Name English
MAZINDOL [USAN]
Common Name English
3H-IMIDAZO(2,1-A)ISOINDOL-5-OL, 5-(4-CHLOROPHENYL)-2,5-DIHYDRO-
Systematic Name English
MAZINDOL [USP IMPURITY]
Common Name English
TERONAC
Brand Name English
42-548
Code English
MAZANOR
Brand Name English
MAZILDENE
Brand Name English
SAH-42548
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 526816
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
EU-Orphan Drug EU/3/15/1444
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
WHO-VATC QA08AA05
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
FDA ORPHAN DRUG 876822
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
NCI_THESAURUS C47795
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
WHO-ATC A08AA05
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
FDA ORPHAN DRUG 16186
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
DEA NO. 1605
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
Code System Code Type Description
WIKIPEDIA
Mazindol
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
RXCUI
6664
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY RxNorm
NCI_THESAURUS
C66057
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
HSDB
3112
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
INN
2895
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
FDA UNII
C56709M5NH
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
ECHA (EC/EINECS)
244-857-0
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
PUBCHEM
4020
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
MESH
D008454
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
DRUG CENTRAL
1640
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
EPA CompTox
DTXSID1023237
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
CAS
22232-71-9
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
ChEMBL
CHEMBL781
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
EVMPD
SUB08656MIG
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
DRUG BANK
DB00579
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
IUPHAR
4797
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY
MERCK INDEX
M7101
Created by admin on Fri Dec 16 16:27:53 UTC 2022 , Edited by admin on Fri Dec 16 16:27:53 UTC 2022
PRIMARY Merck Index