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Details

Stereochemistry ACHIRAL
Molecular Formula C22H18Cl2N8.ClH
Molecular Weight 501.799
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LADUVIGLUSIB HYDROCHLORIDE

SMILES

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

InChI

InChIKey=SCQDMKUZHIGAIB-UHFFFAOYSA-N
InChI=1S/C22H18Cl2N8.ClH/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);1H

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Tau protein kinase I is essential for amyloid beta-protein-induced neurotoxicity.
1993 Aug 15
Glycogen synthase kinase-3β is required for the induction of skeletal muscle atrophy.
2011 Nov
Roles of glycogen synthase kinase 3 in Alzheimer's disease.
2012 Sep
Rictor Undergoes Glycogen Synthase Kinase 3 (GSK3)-dependent, FBXW7-mediated Ubiquitination and Proteasomal Degradation.
2015 May 29
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 Nov
Patents

Sample Use Guides

In ZDF rats, a single oral dose 30 mg/kg of CHIR 99021 rapidly lowered plasma glucose.
Route of Administration: Oral
rostral (r2–3) hindbrain hindbrain neural stem cells are efficiently specified by 1.4 µM CHIR99021
Name Type Language
LADUVIGLUSIB HYDROCHLORIDE
Common Name English
3-PYRIDINECARBONITRILE, 6-((2-((4-(2,4-DICHLOROPHENYL)-5-(5-METHYL-1H-IMIDAZOL-2-YL)-2-PYRIMIDINYL)AMINO)ETHYL)AMINO)-, HYDROCHLORIDE (1:1)
Systematic Name English
CHIR-911 HYDROCHLORIDE
Code English
CHIR-99021 HYDROCHLORIDE
Code English
Code System Code Type Description
FDA UNII
5AW8G37ZX5
Created by admin on Sat Dec 16 16:10:28 GMT 2023 , Edited by admin on Sat Dec 16 16:10:28 GMT 2023
PRIMARY
PUBCHEM
71295844
Created by admin on Sat Dec 16 16:10:28 GMT 2023 , Edited by admin on Sat Dec 16 16:10:28 GMT 2023
PRIMARY
CAS
1797989-42-4
Created by admin on Sat Dec 16 16:10:28 GMT 2023 , Edited by admin on Sat Dec 16 16:10:28 GMT 2023
PRIMARY