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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H13ClN2O
Molecular Weight 284.74
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAZINDOL, (S)-

SMILES

O[C@@]1(N2CCN=C2C3=CC=CC=C13)C4=CC=C(Cl)C=C4

InChI

InChIKey=ZPXSCAKFGYXMGA-INIZCTEOSA-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/t16-/m0/s1

HIDE SMILES / InChI
Mazindol was developed as an appetite suppressant. It exists in a dynamic equilibrium between three isomers (the keto and the R and S–ol forms, respectively) with the R or S–ol being the only relevant forms at physiologic pH. Both S- and R-mazindol supposed to target human serotonin and dopamine transporters. R-mazindol is the biologically relevant enantiomer.

Originator

Curator's Comment: Originator of S-enantiomer of mazindol is unknown. Mazindol was developed at Sandoz.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Molecular mechanism of serotonin transporter inhibition elucidated by a new flexible docking protocol.
2012 Jan
Binding of mazindol and analogs to the human serotonin and dopamine transporters.
2014 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
MAZINDOL, (S)-
Common Name English
3H-IMIDAZO(2,1-A)ISOINDOL-5-OL, 5-(4-CHLOROPHENYL)-2,5-DIHYDRO-, (5S)-
Systematic Name English
Code System Code Type Description
PUBCHEM
57082162
Created by admin on Sat Dec 16 10:14:37 GMT 2023 , Edited by admin on Sat Dec 16 10:14:37 GMT 2023
PRIMARY
CAS
1337994-13-4
Created by admin on Sat Dec 16 10:14:37 GMT 2023 , Edited by admin on Sat Dec 16 10:14:37 GMT 2023
PRIMARY
FDA UNII
B99NL08Q65
Created by admin on Sat Dec 16 10:14:37 GMT 2023 , Edited by admin on Sat Dec 16 10:14:37 GMT 2023
PRIMARY