ChemSpider 2D Image | Bosutinib | C26H29Cl2N5O3

Bosutinib

  • Molecular FormulaC26H29Cl2N5O3
  • Average mass530.446 Da
  • Monoisotopic mass529.164734 Da
  • ChemSpider ID4486102

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

380843-75-4 [RN]
3-Quinolinecarbonitrile, 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]- [ACD/Index Name]
4-[(2,4-Dichlor-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-chinolincarbonitril [German] [ACD/IUPAC Name]
4-[(2,4-Dichloro-5-méthoxyphényl)amino]-6-méthoxy-7-[3-(4-méthyl-1-pipérazinyl)propoxy]-3-quinoléinecarbonitrile [French] [ACD/IUPAC Name]
4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile [ACD/IUPAC Name]
bosutinib [Spanish] [INN]
bosutinib [French] [INN]
bosutinibum [Latin] [INN]
SKI 606
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SKI-606 [DBID]
D03252 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1407
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1407
      L01XE14 Wikidata Q894611
      no pictogram Axon Medchem 1407
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1407
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 4361
      Warning Axon Medchem 1407
    • Target Organs:

      MAPK inhibitor;Src inhibitor;Bcr-Abl inhibitor;CaMK inhibitor;CDK inhibitor TargetMol T0152
    • Chemical Class:

      An aminoquinoline that is 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline bearing additional cyano and methoxy substituents at positions 3 and 6 respectively. ChEBI CHEBI:39112
    • Bio Activity:

      Bcr-Abl Src MedChem Express HY-10158
      Bosutinib (SKI-606) is a novel, dual Src/Abl inhibitor with IC50 of 1.2 nM and 1 nM, respectively.;IC50 value: 1.2 nM/1 nM (Src/Abl) [1] ;Target: Src/Abl ;In vitro: Bosutinib is selective for Src over non-Src family kinases with an IC50 of 1.2 nM, and potently inhibits Src-dependent cell proliferation with an IC50 of 100 nM [1]. Bosutinib significantly inhibits the proliferation of Bcr-Abl-positive leukemia cell lines KU812, K562, and MEG-01 but not Molt-4, HL-60, Ramos, and other leukemia cell lines, with IC50 of 5 nM, 20 nM and 20 nM, respectively, more potently than that of STI-571. Similar to STI-571, Bosutinib displays antiproliferative activity against the Abl-MLV-transformed fibroblasts with IC50 of 90 nM. Bosutinib ablates tyrosine phosphorylation of Bcr-Abl and STAT5 in CML cells and of v-Abl expressed in fibroblasts at the concentration of ~50 nM, 10-25 nM and 200 nM, respectively, leading to the Bcr-Abl downstream signaling inhibition of Lyn/Hck phosphorylation [2]. Alth MedChem Express HY-10158
      Dual inhibitor of Abl and Src kinases (IC50 = 1.2 nM for Src in an enzymatic assay). Displays antiproliferative activity against chronic myelogenous leukemia (CML) cells and decreases the motility and invasion of breast cancer cell lines. Also exhibits potent antiproliferative activity in anchorage-independent, Src-transformed rat fibroblasts (IC50 = 100 nM). Displays selectivity for Src over non-Src family kinases such as growth factor receptor tyrosine kinases. Tocris Bioscience 4361
      Dual inhibitor of Abl and Src kinases (IC50 = 1.2 nM for Src in an enzymatic assay). Displays antiproliferative activity against chronic myelogenous leukemia (CML) cells and decreases the motility and invasion of breast cancer cell lines. Also exhibits potent antiproliferative activity in anchorage-independent, Src-transformed rat fibroblasts (IC50 = 100 nM). Displays selectivity for Src over non- Src family kinases such as growth factor receptor tyrosine kinases. Tocris Bioscience 4361
      Dual Src-Abl inhibitor; antiproliferative Tocris Bioscience 4361
      Enzymes Tocris Bioscience 4361
      Kinases Tocris Bioscience 4361
      MAPK Signaling; Tyrosine Kinase/Adaptors; Cell cycle/Checkpoint;Neuroscience TargetMol T0152
      MAPKK2, MAPKKK2;ABL1, Lyn, HCK, Src;Breakpoint cluster region protein(BCR);Bcr-Abl ;CaMK;CDK 2 TargetMol T0152
      Protein Tyrosine Kinase/RTK; MedChem Express HY-10158
      Src Family Kinases Tocris Bioscience 4361
      Src Kinases Tocris Bioscience 4361

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 649.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 95.8±3.0 kJ/mol
Flash Point: 346.7±31.5 °C
Index of Refraction: 1.652
Molar Refractivity: 141.9±0.4 cm3
#H bond acceptors: 8
#H bond donors: 1
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 2
ACD/LogP: 5.48
ACD/LogD (pH 5.5): 2.28
ACD/BCF (pH 5.5): 9.06
ACD/KOC (pH 5.5): 38.42
ACD/LogD (pH 7.4): 3.98
ACD/BCF (pH 7.4): 464.03
ACD/KOC (pH 7.4): 1967.17
Polar Surface Area: 83 Å2
Polarizability: 56.3±0.5 10-24cm3
Surface Tension: 66.2±5.0 dyne/cm
Molar Volume: 388.3±5.0 cm3

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