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332012-40-5 molecular structure
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4-[({4-[(4-chlorophenyl)amino]furo[2,3-d]pyridazin-7-yl}oxy)methyl]-N-methylpyridine-2-carboxamide

ChemBase ID: 73089
Molecular Formular: C20H16ClN5O3
Molecular Mass: 409.82574
Monoisotopic Mass: 409.09416708
SMILES and InChIs

SMILES:
n1c(c2c(c(n1)OCc1cc(ncc1)C(=O)NC)occ2)Nc1ccc(cc1)Cl
Canonical SMILES:
CNC(=O)c1nccc(c1)COc1nnc(c2c1occ2)Nc1ccc(cc1)Cl
InChI:
InChI=1S/C20H16ClN5O3/c1-22-19(27)16-10-12(6-8-23-16)11-29-20-17-15(7-9-28-17)18(25-26-20)24-14-4-2-13(21)3-5-14/h2-10H,11H2,1H3,(H,22,27)(H,24,25)
InChIKey:
QFCXANHHBCGMAS-UHFFFAOYSA-N

Cite this record

CBID:73089 http://www.chembase.cn/molecule-73089.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[({4-[(4-chlorophenyl)amino]furo[2,3-d]pyridazin-7-yl}oxy)methyl]-N-methylpyridine-2-carboxamide
IUPAC Traditional name
telatinib
Synonyms
BAY 57-9352
Telatinib
CAS Number
332012-40-5
PubChem SID
162038009
PubChem CID
9808844

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S2231 external link Add to cart Please log in.
Data Source Data ID
PubChem 9808844 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.193049  H Acceptors
H Donor LogD (pH = 5.5) 2.9770904 
LogD (pH = 7.4) 2.9771082  Log P 2.9771085 
Molar Refractivity 109.0455 cm3 Polarizability 41.444862 Å3
Polar Surface Area 102.17 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Target
c-Kit expand Show data source
PDGFR expand Show data source
VEGFR expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2231 external link
Biological Activity
Description Telatinib (BAY 57-9352) is a potent inhibitor of VEGFR2, VEGFR3, c-Kit and PDGFRβ with IC50 of 6 nM, 4 nM, 1 nM and 15 nM, respectively.
Targets VEGFR2 VEGFR3 c-Kit PDGFRβ
IC50 6 nM 4 nM 1 nM 15 nM [1]
In Vitro Telatinib has 0.66, 0.17, and 2.5 times higher IC50 values for VEGFR3, c-Kit, and PDGFRβ than VEGFR2, respectively, while Vatalanib exhibits 18, 20, and 16 times higher IC50 values, respectively, indicating that Telatinib has potential benefit over Vatalanib. Telatinib inhibits VEGFR2 autophosphorylation in a whole-cell assay with an IC50 of 19 nM, suppresses VEGF-dependent proliferation of human umbilical vein endothelial cells with an IC50 of 26 nM, and blocks PDGF-stimulated growth of human aortic smooth muscle cells with an IC50 of 249 nM. [3] Telatinib displays little inhibitory activity against the Raf kinase pathway, epidermal growth factor receptor family, the fibroblast growth factor receptor (FGFR) family, and the Tie-2 receptor. [4]
In Vivo Given that tumor development and metastasis are ascribed to deregulated VEGFR signal pathway, Telatinib treatment significantly inhibits tumor growth and metastasis by blocking the VEGFR signaling and subsequently tumor angiogenesis. In addition to the significant inhibition of tumor angiogenesis, Telatinib treatment induces a significant decrease in endothelium-dependent and endothelium-independent vasodilation, as well as reduction in capillary density, leading to an increase in systolic and diastolic blood pressure. [1] Administration of Telatinib as a single agent exhibits a potent anti-tumor activity in multiple human tumor xenograft models including MDA-MB-231 breast cancer, Colo-205 colon cancer, DLD-1 colon cancer, and H460 non-small cell lung cancer, as well as pancreatic and prostate carcinoma in a dose-dependent manner. [2]
Clinical Trials A Phase II study of Telatinib in combination with chemotherapy (Capecitabine and Cisplatin) in subjects with advanced gastric cancer has been completed.
Features
References
[1] Steeghs N, et al. Clin Cancer Res, 2008, 14(11), 3470-3476.
[2] Strumberg D, et al. Br J Cancer, 2008, 99(10), 1579-1585.
[3] Eskens FA, et al. J Clin Oncol, 2009, 27(25), 4169-4176.
[4] Langenberg MH, et al. Clin Cancer Res, 2010, 16(7), 2187-2197.

PATENTS

PATENTS

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INTERNET

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