| Identification | Back Directory | [Name]
Orantinib (SU6668) | [CAS]
252916-29-3 | [Synonyms]
TSU-68
Orantinib
NSC 702827
TSU-68, >=99%
TSU-68 (SU6668)
SU 6668(TSU-68)
Orantinib (SU6668
Orantinib (TSU-68)
TSU-68 (Orantinib,SU6668)
Orantinib (TSU-68, SU6668)
ORANTINIB (SU6668; TSU-68)
TSU-68 (SU6668, Orantinib)
Orantinib (SU6668) USP/EP/BP
ORANTINIB;SU6668;SU 6668;NSC 702827
TSU-68;SU6668; NSC 702827;TSU 68;TSU68
TSU-68 (SU6668, ORANTINIB);SU 6668;TSU68
3-(2,4-DiMethyl-5-((2-oxoindolin-3-ylidene)Methyl)-1H-pyrrol-3-yl)propanoic acid
(E)-3-(2,4-diMethyl-5-((2-oxoindolin-3-ylidene)Methyl)-1H-pyrrol-3-yl)propanoic acid
(Z)-3-(2,4-dimethyl-5-((2-oxoindolin-3-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid
3-[2,4-dimethyl-5-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid
5-[1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-propanoic acid
1H-Pyrrole-3-propanoic acid, 5-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)Methyl]-2,4-diMethyl-
3-[2,4-dimethyl-5-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid
TSU-68
(Z)-3-[2,4-Dimethyl-5-(2-oxo-2,3-dihydro-1H-indol-3-ylidenemethyl)-1H-pyrrol-3-yl]propionic acid
5-[1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-propanoic acid TSU-68 (SU6668, Orantinib) | [Molecular Formula]
C18H18N2O3 | [MDL Number]
MFCD03426212 | [MOL File]
252916-29-3.mol | [Molecular Weight]
310.35 |
| Chemical Properties | Back Directory | [Melting point ]
252-254 °C | [Boiling point ]
590.5±50.0 °C(Predicted) | [density ]
1.328±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4?+-.0.10(Predicted) | [color ]
Orange to Brown |
| Hazard Information | Back Directory | [Uses]
3-[2,4-dimethyl-5-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid is a potent inhibitor of Flk-1/KDR, FGFR1 and PDGFRβ with Ki of 2.1 μM, 1.2 μM, and 8 nM, respectively.
| [Uses]
TSU-68 is a inhibitor that targets vascular endothelial growth factor receptor 2, platelet-derived growth factor receptor β, and fibroblast growth factor receptor 1. The inhibitory effects of TSU-68 t
owards these growth factors lead to substantial antitumor activity and showed potential in its development in therapeutic uses. | [Definition]
3-[2,4-dimethyl-5-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid is an oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is substituted by a 2-(2-carboxyethyl)-3,5-dimethylpyrrol-3-yl group. It is an ATP-competitive inhibitor of the tyrosine kinase activity of fibroblast growth facto receptor 1.
| [Biological Activity]
ATP-competitive PDGFR, VEGF and FGFR inhibitor (IC 50 values are 0.06, 2.43, 3.04 and > 100 μ M at PDGFR β , VEGFR2, FGFR1 and EGFR respectively). Inhibits proliferation of HUVEC and NIH3T3 cells in vitro (IC 50 values are 0.41, 9.3 and 16.5 μ M for VEGF, FGF and PDGF-stimulated growth respectively) and induces > 75% growth inhibition against a broad range of tumor types in vivo . Exhibits antiangiogenic, anti-inflammatory, antimetastatic and proapoptotic activity and is orally active. | [in vitro]
biochemical kinetic studies using isolated flk-1, fgf receptor 1, and pdgf receptor β kinases revealed that tsu-68 has competitive inhibitory properties with respect to atp. in cellular systems, tsu-68 inhibited receptor tyrosine phosphorylation and mitogenesis after stimulation of cells by appropriate ligands [1]. | [in vivo]
oral or i.p. administration of tsu-68 in athymic mice resulted in significant growth inhibition of a diverse panel of human tumor xenografts of glioma, melanoma, lung, colon, ovarian, and epidermoid origin [1]. | [storage]
Store at -20°C | [References]
[1] laird ad, vajkoczy p, shawver lk et al. su6668 is a potent antiangiogenic and antitumor agent that induces regression of established tumors. cancer res. 2000 aug 1;60(15):4152-60.
[2] okamoto i, yoshioka h, takeda k et al. phase i clinical study of the angiogenesis inhibitor tsu-68 combined with carboplatin and paclitaxel in chemotherapy-naive patients with advanced non-small cell lung cancer. j thorac oncol. 2012 feb;7(2):427-33. |
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