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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10ClN3O2S2
Molecular Weight 291.778
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIFENAZOXIDE

SMILES

CC1(CC1)NC2=NS(=O)(=O)C3=C(N2)C=C(Cl)S3

InChI

InChIKey=KYSFUHHFTIGRJN-UHFFFAOYSA-N
InChI=1S/C9H10ClN3O2S2/c1-9(2-3-9)12-8-11-5-4-6(10)16-7(5)17(14,15)13-8/h4H,2-3H2,1H3,(H2,11,12,13)

HIDE SMILES / InChI

Molecular Formula C9H10ClN3O2S2
Molecular Weight 291.778
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tifenazoxide is a thiadiazine derivative patented by Novo Nordisk A/S as the opener of the KATP-regulated potassium channels useful in the treatment of the endocrine system diseases. Tifenazoxide is a selective opener of the beta-cell type (SUR1 / Kir6.2) KATP channel that characterized as competitive inhibitors of glibenclamide binding to membranes of HEK293 cells expressing human SUR1/Kir6.2and as potent inhibitors of insulin release in isolated rat islets. In clinical trials, Tifenazoxide administration leads to a decrease in insulin concentrations 1 h post-dose. This was accompanied by an increase in glucose and growth hormone concentrations (NS), but not of glucagon. During the OGTT a dose-dependent reduction in the 2 h glucose value was observed.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.286 µM [IC50]
PubMed

PubMed

TitleDatePubMed
6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells.
2002 Sep 12
Patents

Patents

Sample Use Guides

.5, 4.5, and 10 mg/kg for seven days.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:10:26 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:26 UTC 2023
Record UNII
Y79681GLMG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIFENAZOXIDE
INN  
INN  
Official Name English
2H-THIENO(3,2-E)-1,2,4-THIADIAZIN-3-AMINE, 6-CHLORO-N-(1-METHYLCYCLOPROPYL)-, 1,1-DIOXIDE
Systematic Name English
NN-414
Code English
tifenazoxide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29711
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
Code System Code Type Description
FDA UNII
Y79681GLMG
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
INN
8317
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
CAS
279215-43-9
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
PUBCHEM
135410911
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107789
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
NCI_THESAURUS
C91024
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
SMS_ID
100000179983
Created by admin on Wed Jul 05 23:10:26 UTC 2023 , Edited by admin on Wed Jul 05 23:10:26 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
Related Record Type Details
ACTIVE MOIETY