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