Art. -Nr.: HY-50751

Linifanib

(Synonyms: ABT-869; AL-39324)

5 Cited Publications

Kundenbewertung

Based on 5 publication(s) in Google Scholar

Linifanib (ABT-869) is a potent and orally active multi-target inhibitor of VEGFR and PDGFR family with IC₅₀s of 4, 3, 66, and 4 nM for KDR, FLT1, PDGFRβ, and FLT3, respectively. Linifanib shows prominent antitumor activity. Linifanib has much less activity against unrelated RTKs, soluble tyrosine kinases, or serine/threonine kinases. Linifanib is a specific miR-10b inhibitor that blocks miR-10b biogenesis.

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Reinheit: 99.39%
CAS. Nr.: 796967-16-3
Formel: C₂₁H₁₈FN₅O
Molecular Weight:375.40

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 1 year , -20°C, 6 months

Linifanib Chemical Structure

CAS. Nr.: 796967-16-3

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Publications (5)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]

Flt-1

3 nM (IC₅₀)

KDR

4 nM (IC₅₀)

PDGFRβ

66 nM (IC₅₀)

FLT3

4 nM (IC₅₀)

CSF-1R

3 nM (IC₅₀)

Kit

14 nM (IC₅₀)

Alle PDGFR Isoform-spezifische Produkte anzeigen :

Alle VEGFR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	8343 nM Compound: Linifanib	Antiproliferative activity activity human A549 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Antiproliferative activity activity human A549 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
EA.hy 926	IC₅₀	2.48 μM Compound: ABT-869	Antiangiogenic activity in human EA.hy 926 cells measured after 24 hrs by MTT assay Antiangiogenic activity in human EA.hy 926 cells measured after 24 hrs by MTT assay	[PMID: 32750566]
HepG2	IC₅₀	4001 nM Compound: Linifanib	Antiproliferative activity activity human HepG2 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Antiproliferative activity activity human HepG2 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
HL-60	IC₅₀	7880 nM Compound: Linifanib	Antiproliferative activity against human HL-60 cells harboring wildtype FLT3 assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Antiproliferative activity against human HL-60 cells harboring wildtype FLT3 assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
HUVEC	IC₅₀	40.11 μM Compound: Linifanib	Antiproliferative activity against HUVEC after 72 hrs by cell titer glo-based fluorescence assay Antiproliferative activity against HUVEC after 72 hrs by cell titer glo-based fluorescence assay	[PMID: 30121211]
HUVEC	IC₅₀	4920 nM Compound: Linifanib	Cytotoxicity against HUVEC cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Cytotoxicity against HUVEC cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
K562	GI₅₀	>20 μM Compound: ABT-869, 4	Antiproliferation activity against human K562 cells expressing wild type BCR/ABL after 72 hrs by MTS method Antiproliferation activity against human K562 cells expressing wild type BCR/ABL after 72 hrs by MTS method	[PMID: 21708468]
K562	IC₅₀	6963 nM Compound: Linifanib	Cytotoxicity against human K562 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Cytotoxicity against human K562 cells assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
MCF7	IC₅₀	17.03 μM Compound: Linifanib	Antiproliferative activity against human MCF7 cells after 72 hrs by cell titer glo-based fluorescence assay Antiproliferative activity against human MCF7 cells after 72 hrs by cell titer glo-based fluorescence assay	[PMID: 30121211]
MOLM-13	GI₅₀	0.037 μM Compound: 3, ABT-869	Cytotoxicity against human MOLM13 cells harboring mutant FLT3 after 72 hrs by MTS assay Cytotoxicity against human MOLM13 cells harboring mutant FLT3 after 72 hrs by MTS assay	[PMID: 23618709]
MOLM-13	GI₅₀	0.037 μM Compound: ABT-869, 4	Antiproliferation activity against human MOLM13 cells expressing FLT3 mutation assessed as cell viability after 72 hrs by MTS method Antiproliferation activity against human MOLM13 cells expressing FLT3 mutation assessed as cell viability after 72 hrs by MTS method	[PMID: 21708468]
MOLM-13	GI₅₀	37 nM Compound: 3, ABT-869	Antiproliferative activity against human MOLM13 cells expressing FLT3-ITD mutant Antiproliferative activity against human MOLM13 cells expressing FLT3-ITD mutant	[PMID: 22726931]
MOLM-13	IC₅₀	19 nM Compound: Linifanib	Antiproliferative activity against human MOLM-13 cells harboring FLT3-ITD mutant assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Antiproliferative activity against human MOLM-13 cells harboring FLT3-ITD mutant assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
MOLT-4	GI₅₀	6.7 μM Compound: ABT-869, 4	Antiproliferation activity against human MOLT4 after 72 hrs by MTS method Antiproliferation activity against human MOLT4 after 72 hrs by MTS method	[PMID: 21708468]
MV4-11	GI₅₀	0.04 μM Compound: ABT-869, 4	Antiproliferation activity against FLT3/ITD harboring human MV4-11 cells after 72 hrs by MTS method Antiproliferation activity against FLT3/ITD harboring human MV4-11 cells after 72 hrs by MTS method	[PMID: 21708468]
MV4-11	IC₅₀	0.69 μM Compound: Linifanib	Antiproliferative activity against human MV4-11 cells after 72 hrs by cell titer glo-based fluorescence assay Antiproliferative activity against human MV4-11 cells after 72 hrs by cell titer glo-based fluorescence assay	[PMID: 30121211]
MV4-11	IC₅₀	3.4 nM Compound: Linifanib	Antiproliferative activity against human MV4-11 cells harboring FLT3-ITD mutant assessed as cell growth inhibition measured after 72 hrs by CCK8 assay Antiproliferative activity against human MV4-11 cells harboring FLT3-ITD mutant assessed as cell growth inhibition measured after 72 hrs by CCK8 assay	[PMID: 35863236]
NFS-60	GI₅₀	4.4 μM Compound: ABT-869	Growth inhibition of mouse NFS-60 cells incubated for 72 hrs by Cell titer-glo assay Growth inhibition of mouse NFS-60 cells incubated for 72 hrs by Cell titer-glo assay	[PMID: 36335744]
NFS-60	IC₅₀	30 nM Compound: ABT-869	Cytotoxicity against mouse NFS-60 cells assessed as cell growth inhibition incubated for 72 hrs by Cell titer-glo assay Cytotoxicity against mouse NFS-60 cells assessed as cell growth inhibition incubated for 72 hrs by Cell titer-glo assay	[PMID: 36335744]
NIH3T3	IC₅₀	4 nM Compound: 17p, ABT-869	Inhibition of VEGF-induced human KDR phosphorylation in mouse 3T3 cells by ELISA Inhibition of VEGF-induced human KDR phosphorylation in mouse 3T3 cells by ELISA	[PMID: 17343372]
RAW264.7	IC₅₀	8.6 μM Compound: ABT-869	Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay	[PMID: 36335744]
RPMI-8226	IC₅₀	5889.4 nM Compound: Chemical probe : ABT-869	Cytotoxicity against human RPMI-8226 cells assessed as reduction in cell growth incubated for 72 hrs by CellTiter 96 aqueous one solution cell proliferation assay Cytotoxicity against human RPMI-8226 cells assessed as reduction in cell growth incubated for 72 hrs by CellTiter 96 aqueous one solution cell proliferation assay	[PMID: 26254279]
RS4-11	GI₅₀	9.2 μM Compound: ABT-869, 4	Antiproliferation activity against human RS4:11 cells expressing wild type FLT3 after 72 hrs by MTS method Antiproliferation activity against human RS4:11 cells expressing wild type FLT3 after 72 hrs by MTS method	[PMID: 21708468]
Sf9	IC₅₀	0.005 μM Compound: ABT-869, 4	Inhibition of recombinant GST-tagged VEGFR2 expressed in Sf9 insect cells after 120 mins by Kinase-Glo assay Inhibition of recombinant GST-tagged VEGFR2 expressed in Sf9 insect cells after 120 mins by Kinase-Glo assay	[PMID: 21708468]
Sf9	IC₅₀	0.007 μM Compound: 3, ABT-869	Inhibition of recombinant GST tagged VEGFR2 (789 to 1356) (unknown origin) transfected in insect sf9 cells after 120 mins by wallac counting analysis Inhibition of recombinant GST tagged VEGFR2 (789 to 1356) (unknown origin) transfected in insect sf9 cells after 120 mins by wallac counting analysis	[PMID: 23618709]
Sf9	IC₅₀	0.02 μM Compound: 3, ABT-869	Inhibition of wild type GST tagged FLT3 kinase (567 to 993) (unknown origin) transfected in insect sf9 cells after 4 hrs by wallac counting analysis Inhibition of wild type GST tagged FLT3 kinase (567 to 993) (unknown origin) transfected in insect sf9 cells after 4 hrs by wallac counting analysis	[PMID: 23618709]
Sf9	IC₅₀	0.02 μM Compound: ABT-869, 4	Inhibition of GST-tagged FLT3 expressing wild type kinase domain expressed in Sf9 insect cells after 4 hrs by Kinase-Glo assay Inhibition of GST-tagged FLT3 expressing wild type kinase domain expressed in Sf9 insect cells after 4 hrs by Kinase-Glo assay	[PMID: 21708468]
Sf9	IC₅₀	0.037 μM Compound: ABT-869, 4	Inhibition of recombinant GST-tagged VEGFR1 expressed in Sf9 insect cells after 120 mins by Kinase-Glo assay Inhibition of recombinant GST-tagged VEGFR1 expressed in Sf9 insect cells after 120 mins by Kinase-Glo assay	[PMID: 21708468]
Sf9	IC₅₀	0.76 μM Compound: 3, ABT-869	Inhibition of recombinant GST tagged Aurora A kinase (123 to 401) (unknown origin) transfected in insect sf9 cells after 90 mins by wallac counting analysis Inhibition of recombinant GST tagged Aurora A kinase (123 to 401) (unknown origin) transfected in insect sf9 cells after 90 mins by wallac counting analysis	[PMID: 23618709]
Sf9	IC₅₀	0.76 μM Compound: ABT-869, 4	Inhibition of recombinant GST-tagged Aurora A expressed in Sf9 insect cells after 90 mins by Kinase-Glo assay Inhibition of recombinant GST-tagged Aurora A expressed in Sf9 insect cells after 90 mins by Kinase-Glo assay	[PMID: 21708468]
U-937	GI₅₀	19 μM Compound: ABT-869, 4	Antiproliferation activity against human FLT3 gene-deficient U937 cells after 72 hrs by MTS method Antiproliferation activity against human FLT3 gene-deficient U937 cells after 72 hrs by MTS method	[PMID: 21708468]

In Vitro

Linifanib (0-10000 nM; 72 hours) inhibits in vitro the cell proliferation of 8305C and 8505C cell lines in a concentration-dependent manner^[3].
Linifanib significantly decreased the levels of phospho-CSF-1R after 24 h and 72 h in both 8505C and 8305C cells^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[3]

Cell Line:

8305C and 8505C cells
Concentration:

0-10000 nM
Incubation Time:

72 hours
Result:

Inhibited the 8305C and 8505C cell proliferation with an IC50 of 0.7 nM and 123.7 nM, respectively.

In Vivo

The synergistic ATC antitumor activity of linifanib (10 mg/kg; p.o.; daily for 33 days)/Irinotecan combination significantly increases the survival of ATC affected mice and induces some complete responses^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Six-week-old CD nu/nu male mice (bearing 8505C ATC cells)^[3]
Dosage:

10 mg/kg
Administration:

P.o.; daily for 33 days
Result:

The combination of linifanib and irinotecan produced a greater survival result than either monotherapy, and resulted in a significant higher median survival of 100 days.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 796967-16-3
Appearance Solid
Molecular Weight 375.40
Formel C₂₁H₁₈FN₅O
Color White to off-white
SMILES

O=C(NC1=CC=C(C2=C3C(N)=NNC3=CC=C2)C=C1)NC4=C(C=CC(C)=C4)F
Synonyms

ABT-869; AL-39324
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	1 year
	-20°C	6 months

Publications (5)

All Flow CytometryCell Proliferation/Viability AssayCell Migration/Invasion AssayWB

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Journal Impact Factor

Nat Biomed Eng

TLR7/8-agonist-loaded nanoparticles promote the polarization of tumour-associated macrophages to enhance cancer immunotherapy. [Abstract]

2018 Aug;2(8):578-588. PMID: 31015631
Sci Transl Med

PP2A inhibition is a druggable MEK inhibitor resistance mechanism in KRAS-mutant lung cancer cells. [Abstract]

2018 Jul 18;10(450):eaaq1093. PMID: 30021885
Int J Oncol

Bromodomain inhibitor jq1 induces cell cycle arrest and apoptosis of glioma stem cells through the VEGF/PI3K/AKT signaling pathway. [Abstract]

2019 Oct;55(4):879-895. PMID: 31485609

Linifanib purchased from MedChemExpress. Usage Cited in: Int J Oncol. 2019 Oct;55(4):879-895. [Abstract]

CSC2078 cells were treated with JQ1 and or Linifanib (5 μM) for 24 h. The cell cycle was analyzed by flow cytometry.

Linifanib purchased from MedChemExpress. Usage Cited in: Int J Oncol. 2019 Oct;55(4):879-895. [Abstract]

CSC2078 cells were treated with JQ1 and or Linifanib (5 μM) for 24 h. Effects of CSC2078 apoptosis were detected by flow cytometry.

Linifanib purchased from MedChemExpress. Usage Cited in: Int J Oncol. 2019 Oct;55(4):879-895. [Abstract]

Western blotting analysis of p-VEGFR2, VEGFR2, PI3K, Akt, p-Akt (Ser473), CyclinB1, Bcl-2 and Bax in control, JQ1 and/or Linifanib (5 μM) treated groups.
iScience

CDC42-effector interaction inhibitors alter patterns of vessel arborization in skin and tumors in vivo. [Abstract]

2025 Jul 14;28(7):112971. PMID: 40950721
Hum Mutat

Integrative Multiscale Analysis Reveals EFNA1-Driven Immune Remodeling Promotes Colorectal Cancer Lymph Node Metastasis. [Abstract]

2026 Jan 14:2026:8553028. PMID: 41542227

Linifanib purchased from MedChemExpress. Usage Cited in: Hum Mutat. 2026 Jan 14:2026:8553028. [Abstract]

CCK‐8 proliferation assay measuring absorbance at 450 nm in cells treated with combined sh‐Efna1 knockdown plus Linifanib (10 μM) versus sh‐NC plus Linifanib.

Linifanib purchased from MedChemExpress. Usage Cited in: Hum Mutat. 2026 Jan 14:2026:8553028. [Abstract]

Representative images and quantification of migrated and invaded cells in Transwell assays under combined treatment conditions (sh − Efna1 + Linifanib (10 μM) vs. sh − NC + Linifanib).

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 10.5 mg/mL (27.97 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.6638 mL

13.3191 mL

26.6383 mL

5 mM

0.5328 mL

2.6638 mL

5.3277 mL

10 mM

0.2664 mL

1.3319 mL

2.6638 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 1.32 mg/mL (3.52 mM); Clear solution

This protocol yields a clear solution of ≥ 1.32 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (13.2 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 1.32 mg/mL (3.52 mM); Clear solution

This protocol yields a clear solution of ≥ 1.32 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (13.2 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 1.32 mg/mL (3.52 mM); Clear solution

This protocol yields a clear solution of ≥ 1.32 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (13.2 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (281 KB)
SDS (563 KB)
- English - EN (563 KB)
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- Portuguese - PT (563 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Albert DH, et al. Preclinical activity of ABT-869, a multitargeted receptor tyrosine kinase inhibitor. Mol Cancer Ther, 2006, 5(4), 995-1006. [Content Brief]

[2]. Monroig-Bosque PDC, et al. OncomiR-10b hijacks the small molecule inhibitor linifanib in human cancers. Sci Rep. 2018;8(1):13106. Published 2018 Aug 30. [Content Brief]

[3]. Banchi M, et al. Synergistic activity of linifanib and irinotecan increases the survival of mice bearing orthotopically implanted human anaplastic thyroid cancer. Am J Cancer Res. 2020;10(7):2120-2127. Published 2020 Jul 1. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.6638 mL	13.3191 mL	26.6383 mL	66.5956 mL
	5 mM	0.5328 mL	2.6638 mL	5.3277 mL	13.3191 mL
	10 mM	0.2664 mL	1.3319 mL	2.6638 mL	6.6596 mL
	15 mM	0.1776 mL	0.8879 mL	1.7759 mL	4.4397 mL
	20 mM	0.1332 mL	0.6660 mL	1.3319 mL	3.3298 mL
	25 mM	0.1066 mL	0.5328 mL	1.0655 mL	2.6638 mL

Linifanib

5 Cited Publications

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Linifanib

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Publications Citing Use of MedChemExpress (MCE) Linifanib

Alle PDGFR Isoform-spezifische Produkte anzeigen

Alle VEGFR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (5)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Linifanib Related Classifications

HY-50751 Related Classifications