(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide
Pelitinib
CAS: 257933-82-7
Molecular Formula: C24H23ClFN5O2
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide - Names and Identifiers
| Name | Pelitinib |
| Synonyms | EKB-569 EKB569 EKB 569 PELITINIB Pelitinib WAY-EKB 569 WAY-EKB 569) WAY-EKB 569 PELITINIB (EKB-569 (E)-N-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide (2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide (2E)-N-{4-[(3-chloro-4-fluorophenyl)aMino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(diMethylaMino)but-2-enaMide (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide 2-Butenamide, N-[4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-, (2E)- |
| CAS | 257933-82-7 |
| EINECS | 803-625-4 |
| InChI | InChI=1/C24H23ClFN5O2/c1-4-33-22-12-20-17(11-21(22)30-23(32)6-5-9-31(2)3)24(15(13-27)14-28-20)29-16-7-8-19(26)18(25)10-16/h5-8,10-12,14H,4,9H2,1-3H3,(H,28,29)(H,30,32)/b6-5+ |
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide - Physico-chemical Properties
| Molecular Formula | C24H23ClFN5O2 |
| Molar Mass | 467.92 |
| Density | 1.34 |
| Melting Point | 173-178°C |
| Boling Point | 655.5±55.0 °C(Predicted) |
| Flash Point | 350.2°C |
| Solubility | Soluble in DMSO (13 mg/ml at 25 °C), methanol, water (<1 mg/ml at 25 °C), and ethano |
| Vapor Presure | 4.64E-17mmHg at 25°C |
| Appearance | grayish white solid |
| Color | white to beige |
| pKa | 12.23±0.43(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.644 |
| Use | An EGFR inhibitor |
| In vitro study | Pelitinib acts on c-erbB-2 more closely related to EGFR than other kinases, such as Src,Cdk4,c-Met,Raf, and MEK/ERK(IC50 range 282 nM( Src))> 20 μm (Cdk4)), showing higher inhibitory activity. Likewise, in A431 cells, Pelitinib treatment significantly inhibited EGFR autophosphorylation, but had no effect on c-Met. Pelitinib effectively inhibited the proliferation of normal human keratinocytes (NHEK) and A431 and MDA-468 tumor cells, with IC50 of 61 nM,125 nM and 260 nM, respectively, while the activity of MCF-7 cells was low, the IC50 was 3.6 μm. In A431 and NHEK cells, Pelitinib inhibits EGF-induced EGFR phosphorylation with an IC50 of 20-80 nM, and also inhibits STAT3 phosphorylation with an IC50 of 30-70 nM. 75-500 nM Pelitinib also specifically inhibits the activation of AKT and ERK1/2 without affecting the NF-κB pathway. In NHEK cells, Pelitinib also effectively inhibited TGF-α-mediated EGFR activation with an IC50 of 56 nM, and inhibited STAT3 and ERK1/2 activation with an IC50 of 60 nM and 62 nM, respectively. |
| In vivo study | In an A431 xenograft model overexpressing EGFR, a single oral dose of 10 mg/kg Pelitinib effectively inhibited EGFR phosphorylation by 90% within 1 hour and> 50% after 24 hours. Pelitinib(20 mg/kg/day) administration inhibits APC Pelitinib selectively inhibits EGFR signaling in airway epithelial cells in vivo. Mouse airway epithelial cell remodeling model, which can be induced by viral infection, has the characteristics of delayed but permanent transformation to Goblet cell metaplasia, Pelitinib(20 mg/kg/day) treatment Corrects epithelial cell remodeling in three ways by completely blocking the increase in ciliated cells and the decrease in Clara cells, and significantly inhibits the metaplasia of goblet cells. |
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | 25 - Toxic if swallowed |
| Safety Description | 45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2811 6.1 / PGIII |
| WGK Germany | 3 |
| Hazard Class | 6.1 |
| Packing Group | III |
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide - Introduction
Pelitinib (EKB-569) is a potent, irreversible EGFR inhibitor with an IC50 of 38.5 nM.
Last Update：2022-10-16 17:15:23
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CAS: 257933-82-7
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CAS: 257933-82-7
Tel: 18301782025
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View History
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide
CS-1226
CS-1226