Gsk-2256098

HCID 46214930CAS 1224887-10-8

Substructure search Find similar structures

Basic information

Standard SMILES: CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl
InChIKey: BVAHPPKGOOJSPU-UHFFFAOYSA-N
Molecular formula: C20H23ClN6O2
Average molar mass: 414.9 g/mol

Overview

GSK2256098 is under investigation in clinical trial NCT02523014 (Vismodegib and FAK Inhibitor GSK2256098 in Treating Patients With Progressive Meningiomas).

Names & identifiers

Preferred name: Gsk-2256098
IUPAC: 2-[[5-chloro-2-[(5-methyl-2-propan-2-ylpyrazol-3-yl)amino]-4-pyridinyl]amino]-N-methoxybenzamide
English name: GSK-2256098
Molecular formula: C20H23ClN6O2
Molecular weight: 414.89

Names & synonyms

1224887-10-8GSK2256098GSK-2256098R7O0O4110G2-[(5-chloro-2-{[3-methyl-1-(propan-2-yl)-1H-pyrazol-5-yl]amino}pyridin-4-yl)amino]-N-methoxybenzamide2-((5-chloro-2-((3-methyl-1-(propan-2-yl)-1H-pyrazol-5-yl)amino)pyridin-4-yl)amino)-N-methoxybenzamideRefChem:144510FAK Inhibitor GSK2256098Focal Adhesion Kinase Inhibitor GSK22560982-((5-Chloro-2-((1-isopropyl-3-methyl-1H-pyrazol-5-yl)amino)pyridin-4-yl)amino)-N-methoxybenzamideMFCD30502650GTPL7939

Show more names

CS-2424GSK-2256099GSK-2256098, GTPL7939GSK 2256098FAK inhibitor GS2256098GSK2256098, 10 mM in DMSO2-(5-chloro-2-(1-isopropyl-3-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methoxybenzamide2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N(methyloxy)benzamide

2-[[5-chloro-2-[[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino]-4-pyridinyl]amino]-N-methoxybenzamideBenzamide, 2-[[5-chloro-2-[[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino]-4-pyridinyl]amino]-N-methoxy-SCHEMBL691518UNII-R7O0O4110GCHEMBL4742157EX-A671HY-100498Q27077884

Database identifiers

CAS: 1224887-10-8
PubChem CID: 46214930
ChEMBL: CHEMBL4742157
UNII: R7O0O4110G

Properties

Computed structural properties

XLogP: 4.5
Topological polar surface area: 93.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 6
Rotatable bonds: 7
Heavy atoms: 29
Formal charge: 0
Complexity: 539

Physicochemical properties

Density: 1.32 · 1.32±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
solubility: 47.33 · DMSO:47.33(Max Conc. mg/mL);114.08(Max Conc. mM)DMF:30.0(Max Conc. mg/mL);72.31(Max Conc. mM)Ethanol:56.0(Max Conc. mg/mL);134.98(Max Conc. mM)Ethanol:PBS (pH 7.2) (1:4):0.2(Max Conc. mg/mL);0.48(Max Conc. mM)
form: A crystalline solid
pka: 5.24 · 5.24±0.10(Predicted)
color: White to khaki
InChI: InChI=1S/C20H23ClN6O2/c1-12(2)27-19(9-13(3)25-27)24-18-10-17(15(21)11-22-18)23-16-8-6-5-7-14(16)20(28)26-29-4/h5-12H,1-4H3,(H,26,28)(H2,22,23,24)
InChIKey: BVAHPPKGOOJSPU-UHFFFAOYSA-N
SMILES: C(NOC)(=O)C1=CC=CC=C1NC1C(Cl)=CN=C(NC2N(C(C)C)N=C(C)C=2)C=1
FDA UNII: 7 O0O4110G · R7O0O4110G
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 280 · P280-P305+P351+P338-P310

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P280-P305+P351+P338-P310

Chemistry & industry

Applications · 2 items

DescriptionGSK2256098 is an inhibitor of focal adhesion kinase (FAK). It is selective for FAK, inhibiting only FAK greater than 50% in a panel of 261 kinases. GSK2256098 inhibits FAK autophosphorylation at tyrosine 397 (Y397) in OVCAR8 ovarian, U87MG glioblastoma, and A549 lung cancer cell lines (IC50s = 15, 8.5, and 12 nM, respectively). It induces apoptosis and increases PARP levels, decreases viability (IC50 = 25 μM), and inhibits colony formation in L3.6P1 cells. GSK2256098 (75 mg/kg per day) also leads to lower tumor weight and fewer metastases in the Ishikawa orthotopic mouse model of uterine cancer.

UsesGSK 2256098 is FAK inhibitor. It can be used in biological study of molecular pathways: endothelial cell FAK-A target for cancer treatment.