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Details

Stereochemistry ACHIRAL
Molecular Formula C22H18Cl2N8.2ClH
Molecular Weight 538.26
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LADUVIGLUSIB DIHYDROCHLORIDE

SMILES

Cl.Cl.CC1=CNC(=N1)C2=CN=C(NCCNC3=NC=C(C=C3)C#N)N=C2C4=CC=C(Cl)C=C4Cl

InChI

InChIKey=OOMHEMQQCHEWDS-UHFFFAOYSA-N
InChI=1S/C22H18Cl2N8.2ClH/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19;;/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32);2*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 C22H18Cl2N8
Molecular Weight 465.338
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12606497

CHIR 99021 is a selective, pyridimidine-based, glycogen synthase kinase 3 inhibitor that is effective at low nanomolar concentrations in enzyme assays and submicromolar concentrations in isolated cells and tissues. Chiron was developing CHIR 99021 for potential use in the treatment of type 2 diabetes mellitus. CHIR 99021 promoted insulin-mediated glucose uptake and increased glucose disposal in rodent models of diabetes. However, there has been no recent development reported.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 10.0 nM [IC50]
Inhibitor
8504
 6.7 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Analysis of Glycogen Synthase Kinase Inhibitors That Regulate Cytochrome P450 Expression in Primary Human Hepatocytes by Activation of β-Catenin, Aryl Hydrocarbon Receptor and Pregnane X Receptor Signaling.
2015-11
Rictor Undergoes Glycogen Synthase Kinase 3 (GSK3)-dependent, FBXW7-mediated Ubiquitination and Proteasomal Degradation.
2015-05-29
Roles of glycogen synthase kinase 3 in Alzheimer's disease.
2012-09
Selectively silencing GSK-3 isoforms reduces plaques and tangles in mouse models of Alzheimer's disease.
2012-05-23
Glycogen synthase kinase-3β is required for the induction of skeletal muscle atrophy.
2011-11
Coordinated waves of gene expression during neuronal differentiation of embryonic stem cells as basis for novel approaches to developmental neurotoxicity testing.
2011-03
Selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo.
2003-03
Potential role of glycogen synthase kinase-3 in skeletal muscle insulin resistance of type 2 diabetes.
2000-02
Increased glycogen synthase kinase-3 activity in diabetes- and obesity-prone C57BL/6J mice.
1999-08
Tau protein kinase I is essential for amyloid beta-protein-induced neurotoxicity.
1993-08-15
Patents

Patents

06489344
6
07037918
6
07045519
11
07425557
5
20020156087
8
20030130289
6
20050054663
5

Sample Use Guides

In Vivo Use Guide
In ZDF rats, a single oral dose 30 mg/kg of CHIR 99021 rapidly lowered plasma glucose.
Route of Administration: Oral
In Vitro Use Guide
rostral (r2–3) hindbrain hindbrain neural stem cells are efficiently specified by 1.4 µM CHIR99021
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:00:14 GMT 2025
Edited
by admin
on Wed Apr 02 08:00:14 GMT 2025
Record UNII
X6BE5J2G31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LADUVIGLUSIB DIHYDROCHLORIDE
Common Name English
CHIR-911 DIHYDROCHLORIDE
Preferred Name English
3-PYRIDINECARBONITRILE, 6-((2-((4-(2,4-DICHLOROPHENYL)-5-(5-METHYL-1H-IMIDAZOL-2-YL)-2-PYRIMIDINYL)AMINO)ETHYL)AMINO)-, HYDROCHLORIDE (1:2)
Systematic Name English
CHIR-99021 DIHYDROCHLORIDE
Code English
Code System Code Type Description
FDA UNII
X6BE5J2G31
Created by admin on Wed Apr 02 08:00:14 GMT 2025 , Edited by admin on Wed Apr 02 08:00:14 GMT 2025
PRIMARY
PUBCHEM
91826519
Created by admin on Wed Apr 02 08:00:14 GMT 2025 , Edited by admin on Wed Apr 02 08:00:14 GMT 2025
PRIMARY
CAS
2109414-84-6
Created by admin on Wed Apr 02 08:00:14 GMT 2025 , Edited by admin on Wed Apr 02 08:00:14 GMT 2025
PRIMARY
Related Record Type Details
Structure of LADUVIGLUSIB
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LADUVIGLUSIB
ACTIVE MOIETY
NIH
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