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    Orantinib

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      Orantinib

      SKU
      O0202

      Category: API's & Intermediates

      Synonyms
      TSU68 , SU 6668 , NSC 702827 , 5-[1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-propanoic acid
      252916-29-3
      CAS-Number
      C18H18N2O3
      Molecular Formula
      310.35
      Molecular Weight

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥98% (HPLC)
      Identity
      1H-NMR
      Appearance
      Orange to red solid

      Properties

      Solvents
      DMSO (10 mg/ml) or DMF (5 mg/ml).
      Short Term Storage
      -20°C
      Use / Stability
      Stable for at least 2 years after receipt when stored at -20°C.
      Handling Advice
      Protect from light and moisture.
      Long Term Storage
      -20°C
      Shipping
      AMBIENT
      Transportation
      Not dangerous goods
      Description
      Orantinib is an orally bioavailable receptor tyrosine kinase inhibitor. Orantinib binds to and inhibits the autophosphorylation of vascular endothelial growth factor receptor 2 (VEGFR2), platelet-derived growth factor receptor (PDGFR), and fibroblast growth factor receptor (FGFR), thereby inhibiting angiogenesis and cell proliferation. It is a potent ATP-competitive inhibitor of PDGFRβ, VEGFR2, and FGFR1 (IC50 = 0.06, 2.4, and 3.0 μM, respectively) but not EGFR (IC50 >100 μM). Orantinib suppresses tumor growth, blocks angiogenesis in tumors and induces apoptosis of tumor vasculature and regression of established tumors. Orantinib inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells, inhibits Aurora kinases B and C (IC50=35 and 210nM, respectively), and inhibits Unc-51-like serine/threonine kinase Ulk3, involved in hedgehog signaling. All together ornatinib exhibits antiangiogenic, anti-inflammatory, antimetastatic and proapoptotic activity.
      InChi
      InChI=1S/C18H18N2O3/c1-10-12(7-8-17(21)22)11(2)19-16(10)9-14-13-5-3-4-6-15(13)20-18(14)23/h3-6,9,19H,7-8H2,1-2H3,(H,20,23)(H,21,22)/b14-9-
      References
      (1) L. Sun, et al., J. Med. Chem. 42, 5120 (1999) , (2) A.D. Laird, et al., Cancer Res. 60, 4152 (2000) , (3) B.D. Smolich, et al., Blood 97, 1413 (2001) , (4) A.D. Laird, et al., FASEB J. 16, 681 (2002) , (5) K. Godl, et al., Cancer Res. 65, 6919 (2005) , (6) D.W. Kim, et al., J. Clin. Endocrinol. Metab. 91, 4070 (2006) , (7) J. Bain, et al., Biochem. J. 408, 297 (2007) , (8) M. Yamamoto, et al., Cancer Res. 68, 9754 (2008) , (9) N. Kammasud, et al., Bioorg. Med. Chem. Lett. 19, 745 (2009) , (10) A. Piirsoo, et al., Biochim. Biophys. Acta 1843, 703 (2014) , (11) L. Kasak, et al., Biochem. 57, 5456 (2018)
      InChi Key
      NHFDRBXTEDBWCZ-ZROIWOOFSA-N
      Smiles
      O=C1NC2=CC=CC=C2/C1=C/C3=C(C)C(CCC(O)=O)=C(C)N3

      Orantinib is an orally bioavailable receptor tyrosine kinase inhibitor. Orantinib binds to and inhibits the autophosphorylation of vascular endothelial growth factor receptor 2 (VEGFR2), platelet-derived growth factor receptor (PDGFR), and fibroblast growth factor receptor (FGFR), thereby inhibiting angiogenesis and cell proliferation. It is a potent ATP-competitive inhibitor of PDGFRβ, VEGFR2, and FGFR1 (IC50 = 0.06, 2.4, and 3.0 μM, respectively) but not EGFR (IC50 >100 μM). Orantinib suppresses tumor growth, blocks angiogenesis in tumors and induces apoptosis of tumor vasculature and regression of established tumors. Orantinib inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells, inhibits Aurora kinases B and C (IC50=35 and 210nM, respectively), and inhibits Unc-51-like serine/threonine kinase Ulk3, involved in hedgehog signaling. All together ornatinib exhibits antiangiogenic, anti-inflammatory, antimetastatic and proapoptotic activity.

      Artikelnummer: O0202 Kategorie: API's & Intermediates
      • Zusätzliche Information

      Zusätzliche Information

      Synonyms

      TSU68, SU 6668, NSC 702827, 5-[1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-propanoic acid

      Purity

      ≥98% (HPLC)

      Appearance

      Orange to red solid

      CAS-Number

      252916-29-3

      Molecular Formula

      C18H18N2O3

      Molecular Weight

      310.35

      Identity

      1H-NMR

      Solvents

      DMSO (10 mg/ml) or DMF (5 mg/ml).

      Smiles

      O=C1NC2=CC=CC=C2/C1=C/C3=C(C)C(CCC(O)=O)=C(C)N3

      InChi Key

      NHFDRBXTEDBWCZ-ZROIWOOFSA-N

      Shipping

      AMBIENT

      Short Term Storage

      -20°C

      Long Term Storage

      -20°C

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      Stable for at least 2 years after receipt when stored at -20°C.

      Transportation

      Not dangerous goods

      References

      (1) L. Sun, et al., J. Med. Chem. 42, 5120 (1999), (2) A.D. Laird, et al., Cancer Res. 60, 4152 (2000), (3) B.D. Smolich, et al., Blood 97, 1413 (2001), (4) A.D. Laird, et al., FASEB J. 16, 681 (2002), (5) K. Godl, et al., Cancer Res. 65, 6919 (2005), (6) D.W. Kim, et al., J. Clin. Endocrinol. Metab. 91, 4070 (2006), (7) J. Bain, et al., Biochem. J. 408, 297 (2007), (8) M. Yamamoto, et al., Cancer Res. 68, 9754 (2008), (9) N. Kammasud, et al., Bioorg. Med. Chem. Lett. 19, 745 (2009), (10) A. Piirsoo, et al., Biochim. Biophys. Acta 1843, 703 (2014), (11) L. Kasak, et al., Biochem. 57, 5456 (2018)

      InChi

      InChI=1S/C18H18N2O3/c1-10-12(7-8-17(21)22)11(2)19-16(10)9-14-13-5-3-4-6-15(13)20-18(14)23/h3-6,9,19H,7-8H2,1-2H3,(H,20,23)(H,21,22)/b14-9-

      Quantity

      25 mg, 100 mg, Bulk

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