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Merck
CN

SMB01404

Sorafenib N-oxide

≥95%

Synonym(s):

4-(4-(3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-2-(methylcarbamoyl)pyridine 1-oxide

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About This Item

Empirical Formula (Hill Notation):
C21H16ClF3N4O4
CAS Number:
583840-03-3
Molecular Weight:
480.82
MDL number:
MFCD25974057
NACRES:
NA.21
Assay:
≥95%
Form:
powder or crystals
Solubility:
DMSO: soluble, methanol: soluble

Key Documents

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InChI key

BQAZCCVUZDIZDC-UHFFFAOYSA-N

InChI

1S/C21H16ClF3N4O4/c1-26-19(30)18-11-15(8-9-29(18)32)33-14-5-2-12(3-6-14)27-20(31)28-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,27,28,31)

SMILES string

CNC(=O)C1=[N+](C=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F)[O-]

biological source

synthetic

assay

≥95%

form

powder or crystals

color

white to off-white

solubility

DMSO: soluble, methanol: soluble

application(s)

clinical research
general analytical
life science and biopharma
metabolomics

storage temp.

−20°C

Quality Level

100

General description

Sorafenib N-Oxide is an active metabolite of Sorafenib and belongs to the class of organic compounds known as diarylethers. Sorafenib is a derivative of niacinamide and phenylurea, primarily known for inhibiting several intracellular and cell surface kinases that are crucial to angiogenesis, including RAF kinases and VEGF receptors. Research indicates that Sorafenib N-Oxide also effectively inhibits FLT3 with internal tandem duplication (ITD) mutations, which helps block the proliferation of MV4-11 acute myeloid leukemia (AML) cells that express FLT3-ITD. Notably, it is selective for AML cell lines with FLT3-ITD mutations, differentiating it from cell lines with the wild-type FLT3. In addition, Sorafenib N-Oxide functions as a linear-mixed inhibitor of the CYP3A4 enzyme, with a Ki value of 15 µM in human liver microsomes. This inhibitory action impacts drug metabolism through the cytochrome P450 (CYP) pathway, specifically CYP3A4, which plays a key role in processing various medications. Due to its selective inhibition and efficacy, Sorafenib N-Oxide is considered a promising candidate for cancer treatment, particularly in the therapeutic management of AML.

Application

Sorafenib N-oxide finds application in metabolomics, biochemical and life science related research.

Features and Benefits

Versatile and adaptable for wide variety of research and metabolomics applications.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000384901
0000384901

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