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Details

Stereochemistry RACEMIC
Molecular Formula C16H13ClN2O.ClH
Molecular Weight 321.201
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAZINDOL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=NIUFFPYONFMTAH-UHFFFAOYSA-N
InChI=1S/C16H13ClN2O.ClH/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;1H

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 Both Sanorex and Mazanor were withdrawn from the market by reason other than safety.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

1973
Primary
SANOREX

Approved Use

Treatment of Duchenne muscular dystrophy.

Launch Date

1986
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
Serial echocardiographic and clinical evaluation of valvular regurgitation before, during, and after treatment with fenfluramine or dexfenfluramine and mazindol or phentermine.
1999 Jul
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
Biochemical and immunohistological changes in the brain of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-treated mouse.
2001 Jan
[Hyperlipidemia with obesity].
2001 Mar
Interactions of tryptamine derivatives with serotonin transporter species variants implicate transmembrane domain I in substrate recognition.
2001 Mar
[Monoaminergic anorectic agents].
2001 Nov
Effects of dopaminergic and cholinergic interactions on rat behavior.
2001 Oct 5
The potential of dopamine agonists in drug addiction.
2002 Apr
Periwound dopaminergic sprouting is dependent on numbers of wound macrophages.
2002 Mar
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
Mazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter.
2002 Sep 12
Changes in GABA(B) receptor mRNA expression in the rodent basal ganglia and thalamus following lesion of the nigrostriatal pathway.
2003
1-Methyl-4-phenylpyridinium accumulates in cerebellar granule neurons via organic cation transporter 3.
2003 Apr
Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat.
2003 Jan
Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands.
2003 Jun 5
Dopamine transporter as target for drug development of cocaine dependence medications.
2003 Oct 31
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
Neurochemical effects of chronic dietary and repeated high-level acute exposure to chlorpyrifos in rats.
2005 Nov
Enhanced dopamine uptake in the striatum following repeated restraint stress.
2005 Sep 1
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 HYDROCHLORIDE
Common Name English
3H-IMIDAZO(2,1-A)ISOINDOL-5-OL, 5-(4-CHLOROPHENYL)-2,5-DIHYDRO-, MONOHYDROCHLORIDE
Systematic Name English
3H-IMIDAZO(2,1-A)ISOINDOL-5-OL, 5-(4-CHLOROPHENYL)-2,5-DIHYDRO-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
TYC95TXB8Q
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID60974091
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
PRIMARY
CAS
26859-70-1
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
3041799
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
PRIMARY
DRUG BANK
DBSALT002359
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
PRIMARY
CAS
58535-70-9
Created by admin on Sat Dec 16 10:14:38 GMT 2023 , Edited by admin on Sat Dec 16 10:14:38 GMT 2023
PRIMARY