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MedKoo Cat#: 205994 | Name: Semaxanib
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Semaxanib
Semaxanib
CAS#204005-46-9 (free base)

Theoretical Analysis

MedKoo Cat#: 205994

Name: Semaxanib

CAS#: 204005-46-9 (free base)

Chemical Formula: C15H14N2O

Exact Mass: 238.1106

Molecular Weight: 238.28

Elemental Analysis: C, 75.61; H, 5.92; N, 11.76; O, 6.71

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,650.00 Ready to ship
2g USD 2,950.00 Ready to ship
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Related CAS #
Semaxanib HCl 204005-46-9 (free base) 1055412-47-9 (Chloro-SU5416)
Synonym
SU5416; SU-5416; SU 5416; Sugen 5416; semoxind; Semaxanib
IUPAC/Chemical Name
(Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one
InChi Key
WUWDLXZGHZSWQZ-WQLSENKSSA-N
InChi Code
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-
SMILES Code
O=C1NC2=C(C=CC=C2)/C1=C/C3=C(C)C=C(C)N3
Appearance
Yellow to orange solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
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.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Semaxanib (SU5416) is a tyrosine-kinase inhibitor drug designed by SUGEN as a cancer therapeutic. It is an experimental stage drug, not licensed for use on human patients outside of clinical trials. Semaxanib is a potent and selective synthetic inhibitor of the Flk-1/KDR vascular endothelial growth factor (VEGF) receptor tyrosine kinase. It targets the VEGF pathway, and both in vivo and in vitro studies have demonstrated antiangiogenic potential. On February 2002, Pharmacia, the then parent of Sugen, prematurely ended Phase III clinical trials of Semaxinib in the treatment of advanced colorectal cancer due to discouraging results.  Other studies, at earlier phases, have since been conducted.  However, due to the prospect of next-generation tyrosine kinase inhibitors and the ineffaciousness of semaxanib in clinic trials, further development of the drug has been discontinued.  A related compound, SU11248 was further developed by Sugen, and then by Pfizer and was FDA-approved as Sunitinib (Sutent) for treatment of renal carcinoma in January 2006. (source: http://en.wikipedia.org/wiki/Semaxanib).      
Biological target:
Semaxinib (SU5416) is a potent and selective inhibitor of VEGFR (Flk-1/KDR) with an IC50 of 1.23 μM.
In vitro activity:
To analyze the fate of OECs and HUVEC upon long-term inhibition of VEGFR-2 and its downstream signaling pathways, inhibitors were added to the medium every other day for up to 10 days. Treatment with SU5416 resulted in a dose-dependent decrease in proliferation of OECs (Figure 2A). Generally, HUVEC demonstrated a higher proliferation rate when compared to OECs, and proliferation of HUVEC was only decreased or inhibited when higher concentrations of SU5416 were used (Figure 2B). Reference: Mol Vis. 2011; 17: 85–98. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3021575/
In vivo activity:
To determine the biofunction of SU5416 in LPS-induced ALI, this study collected BALF from the mice. In comparison with saline group, LPS significantly increased neutrophil cell numbers in BALF of WT and TLR4−/- mice, while neutrophil cells were significantly diminished in TLR4−/- mice (Figure 1A, P<0.01). As a positive control, dexamethasone (DXM) observably inhibited cell population of neutrophil in BALF isolated from two genotype mice (P<0.01). In addition, SU5416 exhibited the similar inhibitory effect on the population of neutrophil cell (P<0.01). Furthermore, co-treatment with SU5416 and DXM significantly alleviated LPS-induced ALI (P<0.01) (Figure 1A). The levels of proinflammatory cytokines (TGF-β, IL-1β, IL-6, and TNF-α) in BALF showed the same trend with the level of neutrophil cells in mice. Moreover, SU5416 and/or DXM significantly reversed LPS-induced proinflammatory factors in BALF (Figure 1B–E). Reference: Drug Des Devel Ther. 2019; 13: 1763–1772. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6536715/
Solvent mg/mL mM
Solubility
DMSO 18.3 76.72
DMF 50.0 209.84
Ethanol 2.0 8.39
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 238.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Mezrich JD, Nguyen LP, Kennedy G, Nukaya M, Fechner JH, Zhang X, Xing Y, Bradfield CA. SU5416, a VEGF receptor inhibitor and ligand of the AHR, represents a new alternative for immunomodulation. PLoS One. 2012;7(9):e44547. doi: 10.1371/journal.pone.0044547. Epub 2012 Sep 6. PMID: 22970246; PMCID: PMC3435281. 2. Thill M, Berna MJ, Kunst F, Wege H, Strunnikova NV, Gordiyenko N, Grierson R, Richard G, Csaky KG. SU5416 induces premature senescence in endothelial progenitor cells from patients with age-related macular degeneration. Mol Vis. 2011 Jan 10;17:85-98. PMID: 21245959; PMCID: PMC3021575. 3. Huang X, Zhu J, Jiang Y, Xu C, Lv Q, Yu D, Shi K, Ruan Z, Wang Y. SU5416 attenuated lipopolysaccharide-induced acute lung injury in mice by modulating properties of vascular endothelial cells. Drug Des Devel Ther. 2019 May 23;13:1763-1772. doi: 10.2147/DDDT.S188858. PMID: 31213766; PMCID: PMC6536715. 4. Grailer JJ, Steeber DA. Vascular endothelial growth factor receptor inhibitor SU5416 suppresses lymphocyte generation and immune responses in mice by increasing plasma corticosterone. PLoS One. 2013 Sep 16;8(9):e75390. doi: 10.1371/journal.pone.0075390. PMID: 24066177; PMCID: PMC3774642.
In vitro protocol:
1. Mezrich JD, Nguyen LP, Kennedy G, Nukaya M, Fechner JH, Zhang X, Xing Y, Bradfield CA. SU5416, a VEGF receptor inhibitor and ligand of the AHR, represents a new alternative for immunomodulation. PLoS One. 2012;7(9):e44547. doi: 10.1371/journal.pone.0044547. Epub 2012 Sep 6. PMID: 22970246; PMCID: PMC3435281. 2. Thill M, Berna MJ, Kunst F, Wege H, Strunnikova NV, Gordiyenko N, Grierson R, Richard G, Csaky KG. SU5416 induces premature senescence in endothelial progenitor cells from patients with age-related macular degeneration. Mol Vis. 2011 Jan 10;17:85-98. PMID: 21245959; PMCID: PMC3021575.
In vivo protocol:
1. Huang X, Zhu J, Jiang Y, Xu C, Lv Q, Yu D, Shi K, Ruan Z, Wang Y. SU5416 attenuated lipopolysaccharide-induced acute lung injury in mice by modulating properties of vascular endothelial cells. Drug Des Devel Ther. 2019 May 23;13:1763-1772. doi: 10.2147/DDDT.S188858. PMID: 31213766; PMCID: PMC6536715. 2. Grailer JJ, Steeber DA. Vascular endothelial growth factor receptor inhibitor SU5416 suppresses lymphocyte generation and immune responses in mice by increasing plasma corticosterone. PLoS One. 2013 Sep 16;8(9):e75390. doi: 10.1371/journal.pone.0075390. PMID: 24066177; PMCID: PMC3774642.
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VEGFA-modified DPSCs combined with LC-YE-PLGA NGCs promote facial nerve injury repair in rats. Heliyon. 2023 Mar 28;9(4):e14626. doi: 10.1016/j.heliyon.2023.e14626. PMID: 37095964; PMCID: PMC10121407. 5: Wanting H, Jian Z, Chaoxin X, Cheng Y, Chengjian Z, Lin Z, Dan C. Using a zebrafish xenograft tumor model to compare the efficacy and safety of VEGFR- TKIs. J Cancer Res Clin Oncol. 2023 Aug;149(9):5975-5987. doi: 10.1007/s00432-022-04560-7. Epub 2023 Jan 7. PMID: 36609710. 6: Qayed WS, Hassan MA, El-Sayed WM, Rogério A Silva J, Aboul-Fadl T. Novel Azine Linked Hybrids of 2-Indolinone and Thiazolodinone Scaffolds as CDK2 Inhibitors with Potential Anticancer Activity: In Silico Design, Synthesis, Biological, Molecular Dynamics and Binding Free Energy Studies. Bioorg Chem. 2022 Sep;126:105884. doi: 10.1016/j.bioorg.2022.105884. Epub 2022 May 21. PMID: 35623140. 7: Chou YF, Lan YH, Hsiao JH, Chen CY, Chou PY, Sheu MJ. Curcuminoids Inhibit Angiogenic Behaviors of Human Umbilical Vein Endothelial Cells via Endoglin/Smad1 Signaling. Int J Mol Sci. 2022 Mar 31;23(7):3889. doi: 10.3390/ijms23073889. PMID: 35409247; PMCID: PMC8998963. 8: Zhu Y, Shu D, Gong X, Lu M, Feng Q, Zeng XB, Zhang H, Gao J, Guo YW, Liu L, Ma R, Zhu L, Hu Q, Ming ZY. Platelet-Derived TGF (Transforming Growth Factor)-β1 Enhances the Aerobic Glycolysis of Pulmonary Arterial Smooth Muscle Cells by PKM2 (Pyruvate Kinase Muscle Isoform 2) Upregulation. Hypertension. 2022 May;79(5):932-945. doi: 10.1161/HYPERTENSIONAHA.121.18684. Epub 2022 Mar 2. PMID: 35232222. 9: Imano H, Kato R, Ijiri Y, Hayashi T. Activation of inflammasomes by tyrosine kinase inhibitors of vascular endothelial growth factor receptor: Implications for VEGFR TKIs-induced immune related adverse events. Toxicol In Vitro. 2021 Mar;71:105063. doi: 10.1016/j.tiv.2020.105063. Epub 2020 Dec 1. PMID: 33271325. 10: Nallan Chakravarthula T, Zagorski J, Zeng Z, Kline JA, Alves NJ. Equivalence Study of Semaxanib from Different Suppliers. Am J Respir Cell Mol Biol. 2020 Dec;63(6):865-868. doi: 10.1165/rcmb.2020-0113LE. PMID: 33258679. 11: Jia Y, Wen X, Gong Y, Wang X. Current scenario of indole derivatives with potential anti-drug-resistant cancer activity. Eur J Med Chem. 2020 Aug 15;200:112359. doi: 10.1016/j.ejmech.2020.112359. Epub 2020 Apr 26. PMID: 32531682. 12: Yang M, Liu H, Zhang Y, Wang X, Xu Z. Moxifloxacin-isatin Hybrids Tethered by 1,2,3-triazole and their Anticancer Activities. Curr Top Med Chem. 2020;20(16):1461-1467. doi: 10.2174/1568026620666200128144825. PMID: 31994464. 13: Ding Z, Zhou M, Zeng C. Recent advances in isatin hybrids as potential anticancer agents. Arch Pharm (Weinheim). 2020 Mar;353(3):e1900367. doi: 10.1002/ardp.201900367. Epub 2020 Jan 21. PMID: 31960987. 14: Hou Y, Shang C, Wang H, Yun J. Isatin-azole hybrids and their anticancer activities. 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