U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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 Both Sanorex and Mazanor were withdrawn from the market by reason other than safety.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
Pharmaceutical cost savings of treating obesity with weight loss medications.
1999 Nov
Anticocaine catalytic antibodies have no affinity for RTI compounds: implications for treatment.
2001 Aug
Dopamine transporter binding in the rat striatum is increased by gestational, perinatal, and adolescent exposure to heptachlor.
2001 Dec
[Monoaminergic anorectic agents].
2001 Nov
1-Methyl-4-phenylpyridinium accumulates in cerebellar granule neurons via organic cation transporter 3.
2003 Apr
Obesity.
2003 Dec
Changes in function and ultrastructure of striatal dopaminergic terminals that regenerate following partial lesions of the SNpc.
2003 Jul
Risk of valvular heart disease associated with use of fenfluramine.
2003 Jun 11
Rapid reduction of ATP synthesis and lack of free radical formation by MPP+ in rat brain synaptosomes and mitochondria.
2003 Jun 13
Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands.
2003 Jun 5
GM1 enhances dopaminergic markers in the brain of aged rats.
2003 Oct
Inhibition of the norepinephrine transporter by the venom peptide chi-MrIA. Site of action, Na+ dependence, and structure-activity relationship.
2003 Oct 10
Strain differences in the distribution of dopamine transporter sites in rat brain.
2003 Sep
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 Sep 15
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
Obesity.
2004 Jun
A model of L-DOPA-induced dyskinesia in 6-hydroxydopamine lesioned mice: relation to motor and cellular parameters of nigrostriatal function.
2004 Jun
Perinatal heptachlor exposure increases expression of presynaptic dopaminergic markers in mouse striatum.
2005 Aug
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 Aug
Pharmacotherapy for weight loss in adults with type 2 diabetes mellitus.
2005 Jan 25
Obesity.
2005 Jun
Neurochemical effects of chronic dietary and repeated high-level acute exposure to chlorpyrifos in rats.
2005 Nov
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 Fri Dec 15 15:11:43 UTC 2023
Edited
by admin
on Fri Dec 15 15:11:43 UTC 2023
Record UNII
C56709M5NH
Record Status Validated (UNII)
Record Version
  • Download
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 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
EU-Orphan Drug EU/3/15/1444
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
WHO-VATC QA08AA05
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
FDA ORPHAN DRUG 876822
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
WHO-ATC A08AA05
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
FDA ORPHAN DRUG 16186
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
DEA NO. 1605
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
Code System Code Type Description
WIKIPEDIA
Mazindol
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
RXCUI
6664
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C66057
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
HSDB
3112
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
INN
2895
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
FDA UNII
C56709M5NH
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
244-857-0
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
PUBCHEM
4020
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
MESH
D008454
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
DRUG CENTRAL
1640
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023237
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
CAS
22232-71-9
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL781
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
EVMPD
SUB08656MIG
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
DRUG BANK
DB00579
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
SMS_ID
100000081747
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
IUPHAR
4797
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY
MERCK INDEX
m7101
Created by admin on Fri Dec 15 15:11:43 UTC 2023 , Edited by admin on Fri Dec 15 15:11:43 UTC 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY