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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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 ( + / - )

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 Both Sanorex and Mazanor were withdrawn from the market by reason other than safety.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
Short-term and long-term clinical evaluation of a non-amphetaminic anorexiant (mazindol) in the treatment of obesity.
1976
Decreased densities of dopamine and serotonin transporters and of vesicular monoamine transporter 2 in severely kainic acid lesioned subregions of the striatum.
2001
Long-term pharmacotherapy of obesity 2000: a review of efficacy and safety.
2001 Aug 13-27
The uptake inhibitors cocaine and benztropine differentially alter the conformation of the human dopamine transporter.
2001 Aug 3
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
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes.
2001 Mar
Role of 5-HT(2a) and 5-HT(2B/2C) receptors in the behavioral interactions between serotonin and catecholamine reuptake inhibitors.
2001 Mar
Effects of dopaminergic and cholinergic interactions on rat behavior.
2001 Oct 5
5-HT3 receptor antagonist MDL 72222 attenuates cocaine- and mazindol-, but not methylphenidate-induced neurochemical and behavioral effects in the rat.
2002 Feb
Chronic but not acute treatment with a metabotropic glutamate 5 receptor antagonist reverses the akinetic deficits in a rat model of parkinsonism.
2002 Jul 1
1-Methyl-4-phenylpridinium (MPP+)-induced functional run-down of GABA(A) receptor-mediated currents in acutely dissociated dopaminergic neurons.
2002 Oct
Three-dimensional quantitative structure-activity relationships of mazindol analogues at the dopamine transporter.
2002 Sep 12
Benzo- and cyclohexanomazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter.
2002 Sep 12
2,3-Disubstituted quinuclidines as a novel class of dopamine transporter inhibitors.
2003 Mar 20
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
Destruction of midbrain dopaminergic neurons by using immunotoxin to dopamine transporter.
2003 Oct
Synergistic interaction between mazindol, an anorectic drug, and swim-stress on analgesic responses in the formalin test in mice.
2004 Jan 23
A model of L-DOPA-induced dyskinesia in 6-hydroxydopamine lesioned mice: relation to motor and cellular parameters of nigrostriatal function.
2004 Jun
Sensitivity to oxidative stress in DJ-1-deficient dopamine neurons: an ES- derived cell model of primary Parkinsonism.
2004 Nov
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
Dysfunction of the cortico-basal ganglia-cortical loop in a rat model of early parkinsonism is reversed by metabotropic glutamate receptor 5 antagonism.
2005 Dec
Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters.
2005 Jul
Obesity.
2005 Jun
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:14:37 UTC 2023
Edited
by admin
on Sat Dec 16 10:14:37 UTC 2023
Record UNII
TYC95TXB8Q
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID60974091
Created by admin on Sat Dec 16 10:14:38 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
PRIMARY
CAS
26859-70-1
Created by admin on Sat Dec 16 10:14:38 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
3041799
Created by admin on Sat Dec 16 10:14:38 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
PRIMARY
DRUG BANK
DBSALT002359
Created by admin on Sat Dec 16 10:14:38 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
PRIMARY
CAS
58535-70-9
Created by admin on Sat Dec 16 10:14:38 UTC 2023 , Edited by admin on Sat Dec 16 10:14:38 UTC 2023
PRIMARY
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ACTIVE MOIETY