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Details

Stereochemistry ACHIRAL
Molecular Formula C20H23N5O
Molecular Weight 349.4295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-(METHYL(2,4,6-TRIMETHYLPHENYL)AMINO)-N-(4-(PYRIDIN-2-YL)-1H-IMIDAZOL-2-YL)ACETAMIDE

SMILES

CN(CC(=O)NC1=NC(=CN1)C2=CC=CC=N2)C3=C(C)C=C(C)C=C3C

InChI

InChIKey=JPLQUMVXDBHHSG-UHFFFAOYSA-N
InChI=1S/C20H23N5O/c1-13-9-14(2)19(15(3)10-13)25(4)12-18(26)24-20-22-11-17(23-20)16-7-5-6-8-21-16/h5-11H,12H2,1-4H3,(H2,22,23,24,26)

HIDE SMILES / InChI

Molecular Formula C20H23N5O
Molecular Weight 349.4295
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:29:07 GMT 2023
Edited
by admin
on Sat Dec 16 11:29:07 GMT 2023
Record UNII
4H59NZJ57G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-(METHYL(2,4,6-TRIMETHYLPHENYL)AMINO)-N-(4-(PYRIDIN-2-YL)-1H-IMIDAZOL-2-YL)ACETAMIDE
Systematic Name English
ACETAMIDE, 2-(METHYL(2,4,6-TRIMETHYLPHENYL)AMINO)-N-(5-(2-PYRIDINYL)-1H-IMIDAZOL-2-YL)-
Systematic Name English
WN-1316
Code English
N-(4-(2-PYRIDYL)-1H-IMIDAZOL-2-YL)-2-(N,2,4,6-TETRAMETHYLANILINO)ACETAMIDE
Systematic Name English
WN1316
Code English
Code System Code Type Description
CAS
1356959-16-4
Created by admin on Sat Dec 16 11:29:07 GMT 2023 , Edited by admin on Sat Dec 16 11:29:07 GMT 2023
PRIMARY
PUBCHEM
56652611
Created by admin on Sat Dec 16 11:29:07 GMT 2023 , Edited by admin on Sat Dec 16 11:29:07 GMT 2023
PRIMARY
FDA UNII
4H59NZJ57G
Created by admin on Sat Dec 16 11:29:07 GMT 2023 , Edited by admin on Sat Dec 16 11:29:07 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
WN1316 has high blood-brain-barrier permeability and water solubility, and boosts both neuronal apoptosis inhibitory protein (NAIP) and NF-E2-related factor 2 (Nrf2) which governed glutathione (GSH)-related anti-oxidation pathway protecting motor neurons against oxidative injuries. Post-onset oral administration of low dose (1-100 undefinedg/kg/day) WN1316 in ALS(SOD1(H46R)) and ALS(SOD1(G93A)) mice resulted in sustained improved motor function and post onset survival rate. Immunohistochemical analysis revealed less DNA oxidative damage and motor neuronal inflammation as well as repression of both microgliosis and astrocytosis, concomitant down regulation of interleukin-1.BETA. and inducible nitric oxide synthase, and preservation of the motoneurons in anterior horn of lumbar spinal cord and skeletal muscle (quadriceps femoris). Thus, WN1316 would be a novel therapeutic agent for ALS.
ACTIVE MOIETY
Originator: Neugen Pharma, Wakunaga Pharmaceutical; Developer: Neugen Pharma; Class: Acetamide, Cytoprotective, Imidazole, Neuroprotectant, Pyridine, Small molecule; Mechanism of Action: Antioxidant, Astrocyte inhibitor, Glial cell inhibitor, Neuronal apoptosis-inhibitory protein stimulant, NF E2 related factor 2 stimulant; Orphan Drug Status: No; On Fast track: No; New Molecular Entity: Yes; Highest Development Phases: Phase I for Amyotrophic lateral sclerosis Most Recent Events: 05 Mar 2015 Neugen Pharma completes an investigator-sponsored phase I trial in Amyotrophic lateral sclerosis (In volunteers) in Japan (PO) (UMIN000015054), 10 Sep 2014 Phase-I clinical trials in Amyotrophic lateral sclerosis (In volunteers) in Japan (PO) (UMIN000015054), 01 Sep 2013 Preclinical trials in Amyotrophic lateral sclerosis in Japan (PO)
ACTIVE MOIETY
Official scientific title of the study: An investigator initiated clinical trial in healthy adults to evaluate safety and pharmacokinetics of WN1316, a candidate drug of amyotrophic lateral sclerosis Results: Oral doses of WN1316 were well tolerated in Japanese healthy male subjects up to 600 micrograms/body (equivalent to the 10 micrograms/kg/day minimum effective dose on ALS mouse model) and no significant safety issue was not observed. In regards to pharmacokinetics, it was confirmed that WN1316 was absorbed and excreted from the body but linearity could not be confirmed owing to too small doses.
ACTIVE MOIETY
Drug: WN 1316(Primary); Indication: Amyotrophic lateral sclerosis; Focus: Adverse reactions, Pharmacokinetics; Most Recent Events: 05 Mar 2015 According to the University Hospital Medical Information Network - Japan record, status changed from recruiting to completed., 11 Sep 2014 New trial record