| Field | Specification |
|---|---|
| Target | |
| Alternative names | SU11654 phosphate; PHA 291639E phosphate |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C22H28FN4O6P |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Toceranib phosphate, also known as SU11654 phosphate or PHA 291639E phosphate, is an orally active receptor tyrosine kinase (RTK) inhibitor that potently inhibits PDGFR, VEGFR, and Kit, with Ki values of 5 nM for PDGFRβ and 6 nM for Flk-1/KDR. It has antitumor and antiangiogenic activity and is used in the treatment of canine mast cell tumors[1][2]. It is supplied as a yellow to orange solid (C22H28FN4O6P, MW 494.45) at 99.23% purity.
Physical & Chemical Properties
| CAS Number | 874819-74-6 |
|---|---|
| Molecular Formula | C22H28FN4O6P |
| Molecular Weight | 494.45 g/mol |
| Purity | 99.23% |
| Appearance | Solid |
| Color | Yellow to orange |
| SMILES | O=C(NCCN1CCCC1)C2=C(NC(/C=C3C(NC4=C\3C=C(C=C4)F)=O)=C2C)C.O=P(O)(O)O |
| Target | PDGFRβ, Flk-1 |
| Signaling Pathway | Protein Tyrosine Kinase/RTK |
| Solubility | In Vitro: DMSO: 1.3 mg/mL (2.63 mM; Requires sonication and warming and adjust pH to 3 with 1 M HCl and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | 4°C, sealed storage, away from moisture. In solvent: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target[1]
|
PDGFRβ 5 nM (Ki) |
Flk-1 6 nM (Ki) |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 1.3 mg/mL (2.63 mM) | requires sonication and warming and adjust pH to 3 with 1 M HCl and heat to 60°C; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); sealed storage, away from moisture; avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
Toceranib phosphate (PHA 291639 phosphate) selectively inhibits tyrosine kinase activity of several split kinase RTK family members, among them PDGFR and Flk-1/KDR (Kis of 5 and 6 nM, respectively)[1]. Mechanisms of acquired Toceranib (TOC) resistance in canine MCT are investigated by generating three resistant sublines, designated TR1, TR2, and TR3, from the Toceranib-sensitive exon 11 ITD c-kit mutant C2 cell line. Toceranib inhibits growth of the parental C2 cells in a dose-dependent manner, with an IC50 of <10 nM. By contrast, the TR1, TR2, and TR3 sublines resist inhibition by Toceranib (IC50> 1,000 nM). Three other KIT RTK inhibitors show a sensitivity profile similar to the observed Toceranib resistance. The parental line and all three sublines remain sensitive to the cytotoxic agents vinblastine (VBL) and CCNU. After 72 hr of culture with increasing Toceranib concentrations, treatment-naive parental C2 cells lift off the culture flask and turn rounded, shrunken, and clumped as Toceranib exposure rises. Toceranib-induced morphologic differences are not identified in the resistant sublines[2].
In Vivo
Toceranib phosphate (PHA 291639 phosphate) given to dogs with cancer significantly lowers both the number and the percentage of Treg in peripheral blood. In dogs treated with Toceranib phosphate (PHA 291639 phosphate) plus cyclophosphamide (CYC), serum IFN-γ concentrations rise significantly and are inversely correlated with Treg numbers after 6 weeks of combination treatment[3].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
Cell Assay[2]
Use the c-kit mutant canine C2 mastocytoma cell line, which originates from spontaneously occurring cutaneous mast cell tumors (MCTs), as the parental cell line. Culture the cells in RPMI 1640 containing 2 mM L-glutamine, 10% FBS, 100 g/mL Streptomycin, and 100 U/mL Penicillin, at 37°C in an incubator with a humidified atmosphere of 5% CO2. Select Toceranib-resistant C2 cells by growing C2 cells in Toceranib at concentrations from 0.02 uM to 0.3 uM, raised in 0.025-0.05 uM increments. Establish three independent Toceranib -resistant sublines over a period of 7 months[2].
Animal Administration[3]
Dogs[3]: Use fifteen client-owned dogs with advanced tumors. Give Toceranib at 2.75 mg/kg once every other day. After 2 weeks, add oral cyclophosphamide (CYC) at 15 mg/m2 daily. Measure Treg numbers and lymphocyte subsets in blood by flow cytometry throughout the 8-week study period. Measure serum IFN-γ concentrations by ELISA.
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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