All Photos(1)
Synonym(s):
4-Ethyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)-phenyl)-3-(pyrazolo[1,5-a]pyrimidin-6-ylethynyl)benzamide, 7rh
Empirical Formula (Hill Notation):
C30H29F3N6O
CAS Number:
Molecular Weight:
546.59
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear
storage temp.
2-8°C
SMILES string
O=C(NC1=CC(C(F)(F)F)=CC(CN2CCN(C)CC2)=C1)C3=CC=C(CC)C(C#CC4=CN5C(N=C4)=CC=N5)=C3
Related Categories
General description
DDR1 Inhibitor 7rh is a small potent kinase inhibitor of discoidin domain receptor-1 (DDR1). It inhibits the tumorigenicity of nasopharyngeal carcinoma (NPC) cells. DDR1 Inhibitor 7rh prevents the proliferation, invasion and adhesion of cancer cells.
Biochem/physiol Actions
DDR1 Inhibitor 7rh is an orally available, potent, ATP-competitive DDR1-selective inhibitor with in vitro and in vivo anti-cancer efficacy.
Compound 7rh is a potent, high affinity (Kd =0.6 nM), ATP-competitive inhibitor against discoidin domain-containing receptor 1 (DDR1; IC50 = 6.8 nM, [ATP] = 100 nM) with significantly reduced potency toward 455 other kinases, including DDR2, Bcr-abl, and c-Kit (IC50 = 101.4 nM, 355 nM and >10 μM, respectively). Inhibitor 7rh reduces DDR1 expression/phosphorylation and downstream signaling in a dose-dependent manner (0.1-2 μM; NCI-H23 NSCLCs), effectively suppressing human cancer cells proliferation (IC50 from 38 nM/K562 to 2.98 μM/NCI-H460) and colony formation (IC50 = 0.56 μM/NCI-H23). Inhibitor 7rh is orally availabe in rats and mice (T1/2 = 15.53 h; Tmax = 4.25 h; Cmax = 1867.5 μg/L, F = 67.4%; 25 mg/kg; rats) and displays in vivo efficacy against Kras (LSLG12Vgeo) tumor growth in mice (50 mg/kg/day p.o.).
Compound 7rh is a potent, high affinity (Kd =0.6 nM), ATP-competitive inhibitor against discoidin domain-containing receptor 1 (DDR1; IC50 = 6.8 nM, [ATP] = 100 nM) with significantly reduced potency toward 455 other kinases, including DDR2, Bcr-abl, and c-Kit (IC50 = 101.4 nM, 355 nM and >10 μM, respectively). Inhibitor 7rh reduces DDR1 expression/phosphorylation and downstream signaling in a dose-dependent manner (0.1-2 μM; NCI-H23 NSCLCs), effectively suppressing human cancer cells proliferation (IC50 from 38 nM/K562 to 2.98 μM/NCI-H460) and colony formation (IC50 = 0.56 μM/NCI-H23). Inhibitor 7rh is orally availabe in rats and mice (T1/2 = 15.53 h; Tmax = 4.25 h; Cmax = 1867.5 μg/L, F = 67.4%; 25 mg/kg; rats) and displays in vivo efficacy against Kras (LSLG12Vgeo) tumor growth in mice (50 mg/kg/day p.o.).
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Mingshan Gao et al.
Journal of medicinal chemistry, 56(8), 3281-3295 (2013-03-26)
Discoidin domain receptor 1 (DDR1) is an emerging potential molecular target for new anticancer drug discovery. We have discovered a series of 3-(2-(pyrazolo[1,5-a]pyrimidin-6-yl) ethynyl)benzamides that are selective and orally bioavailable DDR1 inhibitors. The two most promising compounds (7rh and 7rj)
Chiara Ambrogio et al.
Nature medicine, 22(3), 270-277 (2016-02-09)
Patients with advanced Kirsten rat sarcoma viral oncogene homolog (KRAS)-mutant lung adenocarcinoma are currently treated with standard chemotherapy because of a lack of efficacious targeted therapies. We reasoned that the identification of mediators of Kras signaling in early mouse lung
Antitumor activity of 7RH, a discoidin domain receptor 1 inhibitor, alone or in combination with dasatinib exhibits antitumor effects in nasopharyngeal carcinoma cells
Lu QP, et al.
Oncology Letters, 12(5), 3598-3608 (2016)
Huocong Huang et al.
The Journal of biological chemistry, 291(44), 23208-23223 (2016-10-30)
Pancreatic ductal adenocarcinomas are highly malignant cancers characterized by extensive invasion into surrounding tissues, metastasis to distant organs, and a limited response to therapy. A main feature of pancreatic ductal adenocarcinomas is desmoplasia, which leads to extensive deposition of collagen
Hoon Hur et al.
BMC cancer, 17(1), 87-87 (2017-02-02)
Discoidin domain receptor 1 (DDR1), a receptor tyrosine kinase that utilizes collagen as a ligand, is a key molecule in the progression of solid tumors as it regulates the interaction of cancer cells with the tumor stroma. However, the clinical
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