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GSK 3 inhibitor XVI

GSK 3 inhibitor XVI structure

CAS No:
252917-06-9
Formula:
C22H18Cl2N8
Chemical Name:
GSK 3 inhibitor XVI
Synonyms:
3-Pyridinecarbonitrile,6-[[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-;3-Pyridinecarbonitrile,6-[[2-[[4-(2,4-dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-;6-[[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile;CHIR 99021;CT 99021;CHIR 911;CIHR 99021;CHIR 99201;GSK 3 inhibitor XVI;GSK 3IXV;Laduviglusib;1485056-50-5
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

CHIR-99021 is a GSK-3α/β inhibitor with an IC50 of 10 and 6.7 nM，showing 500-fold selectivity over its closest homologs CDC2 and ERK2, as well as other protein kinases.

CHIR 99021 is a member of the class of aminopyrimidines that is 2-aminopyrimidine substituted at positions N2, 5 and 6 by (5-cyanopyridin-2-yl)ethyl, 4-methylimidazol-2-yl and 2,4-dichlorophenyl groups respectively. It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor. It is a member of imidazoles, a dichlorobenzene, an aminopyrimidine, an aminopyridine, a cyanopyridine, a secondary amino compound and a diamine.

GSK 3 inhibitor XVI Basic Attributes

Molecular Weight：

465.35

Exact Mass：

465.34

EC Number：

1312995-182-4

UNII：

234CMT4GK4

DSSTox ID：

DTXSID90179931

HScode：

29335990

Characteristics

PSA：

115

XLogP3：

4.3

Appearance：

white to light brown

Density：

1.5±0.1 g/cm3

Boiling Point：

784.1±70.0°C at 760 mmHg

Flash Point：

428.0±35.7 °C

Refractive Index：

1.700

Water Solubility：

DMSO: soluble2mg/mL, clear (warmed)

Storage Conditions：

-20°C

Safety Information

Transport codes：

UN 2811 6.1 / PGIII

wgk germany：

hazard class code：

25-36/37/38

safety instructions：

26-36/37/39-45

Marks：

Precautionary statement(s)：

P261-P264-P301 + P310-P305 + P351 + P338

Hazard Statements：

H300-H315-H319-H335

GHS Classification：

|Danger|H300 (95.12%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

Chir 99021

GSK 3 inhibitor XVI Use and Manufacturing

Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that plays a key inhibitory role in both the insulin and Wnt signaling pathways. CHIR99021 is an aminopyrimidine derivative that inhibits GSK3α and GSK3β with IC50 values of 10 and 6.7 nM, respectively. When tested against twenty different protein kinases, this inhibitor shows greater than 500-fold selectivity for GSK3. CHIR99021 activates glycogen synthesis in CHO-IR cells (EC50 = 0.8 μM) and in isolated type 1 diabetic rat skeletal muscle. A single oral dose (30 mg/kg) of CHIR99021 enhances in vivo glucose metabolism in a rodent model of type 2 diabetes. CHIR99021 has also been shown to induce the reprogramming of murine and human somatic cells into stem cells.

Computed Properties

Molecular Weight:465.3
XLogP3:4.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:464.1031480
Monoisotopic Mass:464.1031480
Topological Polar Surface Area:115
Heavy Atom Count:32
Complexity:645
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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