MAZINDOL

US Previously Marketed

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 Search

SMILES

OC1(N2CCN=C2C3=C1C=CC=C3)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

Molecular Formula	C16H13ClN2O
Molecular Weight	284.74
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: DOI: 10.1016/S0196-0644(98)70252-5, Bryson P., 'Comprehensive Reviews in Toxicology: For Emergency Clinicians' (1996), p.491, Retrieved from | https://books.google.es/books? | DOI: 10.1007/978-3-642-57836-6, Kales A., 'The Pharmacology of Sleep' (2012), p. 431, Retrieved from | https://books.google.es/books?id=1O30CAAAQBAJ&dq

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 Both Sanorex and Mazanor were withdrawn from the market by reason other than safety.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).

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 206 Sources: http://www.indianapharmacists.org/Files/Continuing%20Education/2013%20Drug%20Treatments%20in%20Obesity.pdf	Primary		Approved 8583	SANOREX Approved Use Unknown Launch Date 1973
Duchenne muscular dystrophy 18 Sources: http://www.fda.gov/ohrms/dockets/dailys/04/june04/060304/84n-0102-lst0101-01.pdf	Primary		Approved 8583	SANOREX Approved Use Treatment of Duchenne muscular dystrophy. Launch Date 1986

C_max

Value	Dose	Co-administered	Analyte	Population
4.09 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27066959/	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

Value	Dose	Co-administered	Analyte	Population
35.63 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27066959/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27066959/	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

Vendor/Aggregator	ID	URL
AA Blocks	AA007OZH	https://www.aablocks.com/goods/Goods/detail?id=AA007OZH
Achemtek	0104-003449	http://www.achemtek.com/22232-71-9
Adooq BioScience	A15154	https://www.adooq.com/mazindol.html
AHH Chemical co.,ltd	MT-53453	http://www.ahhchemical.com/product/MT-53453.html
Alsachim	3075	http://www.alsachim.com/product-C4150-glo.bal-view.html
Ambinter	Amb17616698	http://www.ambinter.com/reference/17616698
Angene	AGN-PC-09QMHZ	http://www.angenechemical.com/productshow/AGN-PC-09QMHZ.html
Anward	ANW-63061	http://www.anward.com/pro_result/49512
Aurora Fine Chemicals LLC	A17.875.774	http://online.aurorafinechemicals.com/info?ID=A17.875.774
Aurum Pharmatech LLC	W-5129	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5129-Mazindol-MFCD00864480
Chem Scene	CS-0777	http://www.chemscene.com/Mazindol.html
ChemMol	30102264	http://www.chemmol.com/chemmol/30102264.html
ChemMol	49401134	http://www.chemmol.com/chemmol/49401134.html
ChemMol	99050119	http://www.chemmol.com/chemmol/99050119.html
Clearsynth	CS-EB-01267	https://www.clearsynth.com/en/CSEB01267.html
Clearsynth	CS-ER-01232	https://www.clearsynth.com/en/CSER01232.html
Finetech	FT-0670955	http://www.finetechnology-ind.com/prod/detail/pub/1246815-50-8.html
Glentham Life Sciences	GP5777	http://www.glentham.com/products/product/GP5777/
MedChem Express	HY-15279	http://www.medchemexpress.com/mazindol.html
OChem	3834	http://www.ocheminc.com/index.php?act=psearch&pid=232M719
Sigma-Aldrich	1375309_USP	https://www.sigmaaldrich.com/catalog/product/usp/1375309?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M2017_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/m2017?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S534588	http://www.smolecule.com/products/s534588
THE BioTek	bt-273644	https://www.thebiotek.com/product/inhibitors/bt-273644

PubMed

Title	Date	PubMed
Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants.	2006-01-27	16272152
A reliable model of intravenous MDMA self-administration in naïve mice.	2006-01	16362403
Dysfunction of the cortico-basal ganglia-cortical loop in a rat model of early parkinsonism is reversed by metabotropic glutamate receptor 5 antagonism.	2005-12	16324110
Differential effects of dopamine and psychoactive drugs on dopamine transporter phosphorylation and regulation.	2005-11	16181646
Neurochemical effects of chronic dietary and repeated high-level acute exposure to chlorpyrifos in rats.	2005-11	16081522
Enhanced dopamine uptake in the striatum following repeated restraint stress.	2005-09-01	15945060
Endothelin-1 inhibits the neuronal norepinephrine transporter in hearts of male rats.	2005-08-01	16005303
The interaction of methylphenidate and benztropine with the dopamine transporter is different than other substrates and ligands.	2005-08-01	15950948
Perinatal heptachlor exposure increases expression of presynaptic dopaminergic markers in mouse striatum.	2005-08	16112329
Recognition of benztropine by the dopamine transporter (DAT) differs from that of the classical dopamine uptake inhibitors cocaine, methylphenidate, and mazindol as a function of a DAT transmembrane 1 aspartic acid residue.	2005-08	15879005
Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters.	2005-07	15831439
Dopaminergic innervation of the human striatum in Parkinson's disease.	2005-07	15726582
Obesity.	2005-06	16135277
Mechanism of 1-methyl-4-phenylpyridinium-induced dopamine release from PC12 cells.	2005-05	16176067
Effects of monoamine reuptake inhibitors on wet-dog shakes mediated by 5-HT2A receptors in ACTH-treated rats.	2005-05	15894065
Inhibiting BDNF expression by antisense oligonucleotide infusion causes loss of nigral dopaminergic neurons.	2005-03	15698637
Pharmacotherapy for weight loss in adults with type 2 diabetes mellitus.	2005-01-25	15674929
Hypersomnia.	2005	16416710
Pharmacotherapy for obesity.	2005	15977970
Diabesity: are weight loss medications effective?	2005	15783244
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.	2004-12	15610165
Sensitivity to oxidative stress in DJ-1-deficient dopamine neurons: an ES- derived cell model of primary Parkinsonism.	2004-11	15502868
Low dose pramipexole is neuroprotective in the MPTP mouse model of Parkinson's disease, and downregulates the dopamine transporter via the D3 receptor.	2004-10-11	15473914
Binding of [3H]mazindol to cardiac norepinephrine transporters: kinetic and equilibrium studies.	2004-07	15300361
Obesity.	2004-06	15652036
A model of L-DOPA-induced dyskinesia in 6-hydroxydopamine lesioned mice: relation to motor and cellular parameters of nigrostriatal function.	2004-06	15207268
[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry].	2004-05	15712903
The inhibitory role of methylation on the binding characteristics of dopamine receptors and transporter.	2004-03	15154679
Uptake inhibitors but not substrates induce protease resistance in extracellular loop two of the dopamine transporter.	2004-03	14978248
Dopamine agonist 3-PPP fails to protect against MPTP-induced toxicity.	2004-02	15002733
Synergistic interaction between mazindol, an anorectic drug, and swim-stress on analgesic responses in the formalin test in mice.	2004-01-23	14729223
Chronic intoxication with 3-nitropropionic acid in rats induces the loss of striatal dopamine terminals without affecting nigral cell viability.	2004-01-16	14700739
Dopamine transmission in DYT1 dystonia.	2004	14509654
Obesity.	2003-12	15555115
Dependence and chronic psychosis with D-nor-pseudoephedrine.	2003-12	14680722
The human dopamine transporter forms a tetramer in the plasma membrane: cross-linking of a cysteine in the fourth transmembrane segment is sensitive to cocaine analogs.	2003-11-14	14519759
Apparent opposite effects of tetrabenazine and reserpine on the toxic effects of 1-methyl-4-phenylpyridinium or 6-hydroxydopamine on nigro-striatal dopaminergic neurons.	2003-11-07	14556940
Dopamine transporter as target for drug development of cocaine dependence medications.	2003-10-31	14612141
Inhibition of the norepinephrine transporter by the venom peptide chi-MrIA. Site of action, Na+ dependence, and structure-activity relationship.	2003-10-10	12885787
GM1 enhances dopaminergic markers in the brain of aged rats.	2003-10	14552908
Destruction of midbrain dopaminergic neurons by using immunotoxin to dopamine transporter.	2003-10	14514035
Dual effects of intermittent or continuous L-DOPA administration on gene expression in the globus pallidus and subthalamic nucleus of adult rats with a unilateral 6-OHDA lesion.	2003-09-15	12827644
Strain differences in the distribution of dopamine transporter sites in rat brain.	2003-09	14499307
Acquired narcolepsy in an acromegalic patient who underwent pituitary irradiation.	2003-08-26	12939432
Serotonin transporter and MAO-B levels in monoamine nuclei of the human brainstem are normal in major depression.	2003-07-10	12849931
Changes in function and ultrastructure of striatal dopaminergic terminals that regenerate following partial lesions of the SNpc.	2003-07	12871574
Rapid reduction of ATP synthesis and lack of free radical formation by MPP+ in rat brain synaptosomes and mitochondria.	2003-06-13	12763610
Risk of valvular heart disease associated with use of fenfluramine.	2003-06-11	12801402
Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands.	2003-06-05	12757963
Changes in GABA(B) receptor mRNA expression in the rodent basal ganglia and thalamus following lesion of the nigrostriatal pathway.	2003	12927208

Patents

Sample Use Guides

In Vivo Use Guide

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

C6 glioma cells stably expressing hDAT were treated with 10 nM of mazindol to test its binding to the dopamine transporter.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:44 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:44 GMT 2025`
Record UNII	C56709M5NH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MAZINDOL CIV

Preferred Name

English

MAZINDOL

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 [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