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SML2653

Sigma-Aldrich

Sorafenib

≥98% (HPLC), powder, kinase inhibitor

Synonym(s):

4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-2-pyridinecarboxamide, BAY 43-9006, BAY43-9006, N-[4-Chloro-3-(trifluoromethyl)phenyl]-N′-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea

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About This Item

Empirical Formula (Hill Notation):
C21H16ClF3N4O3
CAS Number:
284461-73-0
Molecular Weight:
464.82
MDL number:
MFCD06411450
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Sorafenib, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

FC(F)(F)c1c(ccc(c1)NC(=O)Nc2ccc(cc2)Oc3cc(ncc3)C(=O)NC)Cl

InChI

1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)

InChI key

MLDQJTXFUGDVEO-UHFFFAOYSA-N

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Biochem/physiol Actions

Sorafenib (BAY 43-9006) is an orally active kinase inhibitor that exerts broad-spectrum anticancer efficacy in vitro and in vivo via targeting b-Raf, c-Raf (Raf-1), as well as several receptor tyrosine kinases involved in neovascularization and tumor progression, including vascular endothelial growth factor receptors 2/3 (VEGFR-2/Flk-1/KDR, VEGFR-3), platelet-derived growth factor receptor-beta (PDGFR-ß), Flt-3, c-KIT, FGFR-1 (Flt-2) and RET.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H360FD,H362,H372,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Lact. - Repr. 1B - STOT RE 1

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000374180
0000374182
0000374180
0000374182
0000260929

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Scott M Wilhelm et al.
Cancer research, 64(19), 7099-7109 (2004-10-07)
The RAS/RAF signaling pathway is an important mediator of tumor cell proliferation and angiogenesis. The novel bi-aryl urea BAY 43-9006 is a potent inhibitor of Raf-1, a member of the RAF/MEK/ERK signaling pathway. Additional characterization showed that BAY 43-9006 suppresses
Hung Huynh et al.
International journal of oncology, 54(3), 1123-1133 (2019-02-13)
Mutations affecting the Wnt/β‑catenin pathway have been identified in 26‑40% of hepatocellular carcinoma (HCC) cases. Aberrant activation of this pathway leads to uncontrolled cell proliferation and survival. Thus, identifying Wnt/β‑catenin pathway inhibitors may benefit a subset of patients with HCC.
Francesca Carlomagno et al.
Journal of the National Cancer Institute, 98(5), 326-334 (2006-03-02)
Medullary and papillary thyroid carcinomas are often associated with oncogenic activation of the RET tyrosine kinase. We evaluated whether the biaryl urea BAY 43-9006, which is known to inhibit several other tyrosine kinases, blocks RET kinase function and oncogenic activity.
Mater H Mahnashi et al.
Pharmaceuticals (Basel, Switzerland), 15(2) (2022-02-27)
Over the past few decades, the development of broad-spectrum anticancer agents with anti-angiogenic activity has witnessed considerable progress. In this study, a new series of pyrazolo[3,4-d]pyrimidines based on a phenylfuroxan scaffold were designed, synthesized, and evaluated, in terms of their
Scott Wilhelm et al.
Current pharmaceutical design, 8(25), 2255-2257 (2002-10-09)
The drug design and discovery efforts described in the previous section led to the development of a novel, small molecule Raf-1 kinase inhibitor, BAY 43-9006, which belongs to a class that can be broadly described as bis-aryl ureas (Figure 1).
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