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204005-46-9 (SU5416)

1

Identification

SU5416 SU5416
Name SU5416
Formula C15H14N2O
MW 238.28
CAS No. 204005-46-9
EINECS
Smiles O=C(NC1=CC=CC=C/21)C2=C/C3=C(C)C=C(C)N3
Synonyms Semaxinib;SU-5416;SU 5416; (Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one
InChI InChI=1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8-
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Introduction

Semaxanib (SU5416) is a potent and selective VEGFR(Flk-1/KDR) inhibitor with IC50 of 1.23 μM, 20-fold more selective for VEGFR than PDGFRβ, lack of activity against EGFR, InsR and FGFR. IC50 value: 1.23 uM [1] Target: VEGFR in vitro: Semaxanib inhibits VEGF-dependent phosphorylation of the Flk-1 receptor in Flk-1-overexpressing NIH 3T3 cells with IC50 of 1.04 μM.

Background Information

Inhibitor of vascular endothelial growth factor receptor (VEGFR) ......by AOBIOUS INC
SU 5416 is an inhibitor of vascular endothelial growth factor receptor (VEGFR) that also inhibits other tyrosine kinases KIT, MET, FLT3 and RET. ......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
Semaxanib, also known as SU5416, is a quinolone derivative with potential antineoplastic activity. Semaxanib reversibly inhibits ATP binding to the tyrosine kinase domain of vascular endothelial growth factor receptor 2 (VEGFR2), which may inhibit VEGF-st ......by BOC Sciences
A 10 mM (5 mg in 2098 µl) of the VEGFR kinase inhibitor SU-5416 (Cat. No. 9491) in anhydrous DMSO. ......by BioVision, Inc.,
SU-5416 is a potent tyrosine kinase inhibitor best known as an inhibitor of the vascular endothelial growth factor receptor (VEGFR-2; Flk-1/KDR). In addition to inhibiting VEGFR-2 (IC₅₀ = 1 μM), SU-5416 also inhibits PDGFR (IC₅₀ = 20 μM), c-Kit (IC₅₀ = 30 nM), RET (IC₅₀ = 170 nM), Flt-3 (IC₅₀ = 160 nM), ABL (IC₅₀ = 11 μM), and ALK (IC₅₀ = 1.2 μM).SU 5416 does not inhibit epidermal growth factor (EGFR) or fibroblast growth factor receptor (FGFR) tyrosine kinases (IC₅₀ > 100 μM). Acts as a suppressor of tumor vascularization, preventing the growth of multiple tumor types. ......by BioVision, Inc.,
SU5416 is a potent and selective inhibitor of the VEGFR (Flk-1/KDR) that inhibits tyrosine kinase catalysis, and inhibits autophosphorylation of the Flk-1 receptor with an IC50 of 1.23±0.2 μM (n=4) using an ELISA-based biochemical kinase assay. ......by MedChemexpress Co., Ltd.
Semaxanib, also known as SU5416, is a quinolone derivative with potential antineoplastic activity. Semaxanib reversibly inhibits ATP binding to the tyrosine kinase domain of vascular endothelial growth factor receptor 2 (VEGFR2), which may inhibit VEGF-stimulated endothelial cell migration and proliferation and reduce the tumor microvasculature. This agent also inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells. ......by MedKoo Biosciences, Inc.
A potent and specific VEGFR2 (KDR/Flk-1) inhibitor with IC50 of 1.04 uM; displays no inhibitory activity against EGFR and FGFR; inhibits autophosphorylation of the Flk-1 receptor with IC50 of 1.23 uM in ELISA assays, inhibits VEGF-driven mitogenesis of HUVECs with IC50 of 0.04 uM; affects tumor vascular density and vascular leakage in vivo.Solid TumorsPhase 1 Discontinued ......by ProbeChem
Semaxanib (SU5416) is a potent and selective VEGFR(Flk-1/KDR) inhibitor with IC50 of 1.23 _mu_M, 20-fold more selective for VEGFR than PDGFR_beta_, lack of activity against EGFR, InsR and FGFR. ......by Target Molecule Corp.
Inhibitor of vascular endothelial growth factor receptor (VEGFR) that also inhibits other tyrosine kinases KIT, MET, FLT3 and RET. Displays no activity against EGFR, HER2, IGF1R and PDGFR. Inhibits tumor vascularization and growth of multiple tumor types. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:yellow solid EBNumber:EB000024362

Storage condition

Storage condition:Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Stock solution storage:0 - 4 C for short term (days to weeks), or -20 C for long term (months). Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. by MedKoo Biosciences, Inc.
Desiccate at -20°C by Tocris Bioscience Inc.

Solubility

DMSO 20 mg/ml Ethanol 8 mg/ml by MedChemexpress Co., Ltd.
Soluble in DMSO, not in water by MedKoo Biosciences, Inc.
Soluble to 100 mM in DMSO by Tocris Bioscience Inc.
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Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
SU5416 Pfizer Inc Metastatic colorectal cancer 1999/11/30 2007/9/1 Phase 3 Clinical
SU5416 Renal tumor 2000/12/31 Phase 2 Clinical
SU5416 Stage IV melanoma 2001/3/31 2003/9/1 Phase 2 Clinical
SU5416 City of Hope Medical Center Metastatic renal cancer 2000/11/30 2007/2/28 Phase 2 Clinical
SU5416 University of Chicago Hormone refractory prostate cancer 2000/6/30 2006/1/1 Phase 2 Clinical
SU5416 - Discontinued
SU5416 - Phase 2
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Safety Data of SU5416

Hazard Symbols : Xi
Risk Statements : R36/37/38
Safety Statements : S26;S36
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Spectral Information

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Suppliers List

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Related Products

Other Forms of 204005-46-9

Name CAS No Formula MW

Recommended Compounds in VEGFR

Name CAS No Formula MW
BIBF 1202 894783-71-2 C30H31N5O4 525.6
SKLB1002 1225451-84-2 C13H12N4O2S2 320.39
Vandetanib (hydrochloride) 524722-52-9 C22H25BrClFN4O2 511.81
Vandetanib (trifluoroacetate) 338992-53-3 C24H25BrF4N4O4 589.38
WHI-P154 211555-04-3 C16H14BrN3O3 376.2
ZM323881 (hydrochloride) 193000-39-4 C22H19ClFN3O2 411.86
ZM 306416 690206-97-4 C16H13ClFN3O2 333.74
Tanshinone IIA 568-72-9 C19H18O3 294.34
R1530 882531-87-5 C18H14ClFN4O 356.78
Oglufanide 38101-59-6 C16H19N3O5 333.34
SKLB610 1125780-41-7 C21H16F3N3O3 415.37
AZD2932 883986-34-3 C24H25N5O4 447.4864
Toceranib (phosphate) 874819-74-6 C22H28FN4O6P 494.45
Sunitinib 557795-19-4 C22H27FN4O2 398.47
Regorafenib (monohydrate) 1019206-88-2 C21H17ClF4N4O4 500.83
Tyrphostin A9 10537-47-0 C18H22N2O 282.38
TAK-593 1005780-62-0 C23H23N7O3 445.47
ZM323881 193001-14-8 C22H18FN3O2 375.4
SAR131675 1433953-83-3 C18H22N4O4 358.39
JI-101 900573-88-8 C22H20BrN5O2 466.33

Recommended Compounds in Same Indication

Name CAS No Formula MW
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
Regorafenib 755037-03-7 C21H15ClF4N4O3 482.82
Olaparib 763113-22-0 C24H23FN4O3 434.46
Regorafenib (Hydrochloride) 835621-07-3 C21H16Cl2F4N4O3 519.28
Trametinib 871700-17-3 C26H23FIN5O4 615.39
KX2-391 897016-82-9 C26H29N3O3 431.53
Bicalutamide 90357-06-5 C18H14F4N2O4S 430.37
Tivantinib 905854-02-6 C23H19N3O2 369.42
IDO5L 914471-09-3 C9H7ClFN5O2 271.6356
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Dovitinib 405169-16-6 C21H21FN6O 392.43
SB-590885 405554-55-4 C27H27N5O2 453.54
Sunitinib 557795-19-4 C22H27FN4O2 398.47
Brivanib (alaninate) 649735-63-7 C22H24FN5O4 441.46
Linsitinib 867160-71-2 C26H23N5O 421.49
Fenretinide 65646-68-6 C26H33NO2 391.55
Retaspimycin 857402-23-4 C31H45N3O8 587.7
Retaspimycin (Hydrochloride) 857402-63-2 C31H46ClN3O8 624.17
Bafetinib 859212-16-1 C30H31F3N8O 576.6154
AT13387 912999-49-6 C24H31N3O3 409.52
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Route of Synthesis

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References

[1]. Fong TA, et al. SU5416 is a potent and selective inhibitor of the vascular endothelial growth factor receptor (Flk-1/KDR) that inhibits tyrosine kinase catalysis, tumor vascularization, and growth of multiple tumor types. Cancer Res, 1999, 59(1), 99-106.

[2]. Vajkoczy P, et al. Inhibition of tumor growth, angiogenesis, and microcirculation by the novel Flk-1 inhibitor SU5416 as assessed by intravital multi-fluorescence videomicroscopy. Neoplasia, 1999, 1(1), 31-41.

Protocol Reference

Fong et al (1999) SU5416 is a potent and selective inhibitor of the vascular endothelial growth factor receptor (Flk-1/KDR) that inhibits tyrosine kinase catalysis, tumor vascularisation, and growth of multiple tumor types. Cancer Res. 59 99. PMID: 9892193.

Smolich et al (2001) The antiangiogenic protein kinase inhibitors SU5416 and SU6668 inhibit the SCF receptor (c-Kit) in a human myeloid leukemia cell line and in acute myeloid leukemia blasts. Blood 97 1413. PMID: 11222388.

Mologni et al (2006) Inhibition of RET tyrosine kinase by SU5416. J.Mol.Endocrinol. 37 199. PMID: