An active metabolite of sorafenib
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Parent Compound(s)
10009644Sorafenib 35612Sorafenib (tosylate)
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Sorafenib N-oxide

Item No. 27830

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-2-pyridinecarboxamide, 1-oxide
CAS Number
583840-03-3
Synonyms
  • BAY 67-3472
Molecular Formula
C21H16ClF3N4O4
Formula Weight
480.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Very slightly soluble (warmed)
SMILES
ClC1=C(C(F)(F)F)C=C(NC(NC2=CC=C(OC3=CC=[N+]([O-])C(C(NC)=O)=C3)C=C2)=O)C=C1
InChi Code
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)
InChi Key
BQAZCCVUZDIZDC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    Sorafenib N-oxide is an active metabolite of sorafenib (BAY 43-9006; Item No. 10009644), an inhibitor of Raf-1, B-RAF, and receptor tyrosine kinases.1 Sorafenib N-oxide inhibits FLT3 that contains the internal tandem duplication mutation (FLT3-ITD; Kd = 70 nM) and inhibits proliferation of MV4-11 acute myeloid leukemia (AML) cells expressing FLT3-ITD (IC50 = 25.8 nM). It is selective for AML cell lines containing FLT3-ITD over lines containing wild-type FLT3 (IC50s = 3.9-13.3 µM). Sorafenib N-oxide is also a linear-mixed inhibitor of the cytochrome P450 (CYP) isoform CYP3A4 (Ki = 15 µM in human liver microsomes).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inaba, H., Rubnitz, J.E., Coustan-Smith, E., et al. Phase I pharmacokinetic and pharmacodynamic study of the multikinase inhibitor sorafenib in combination with clofarabine and cytarabine in pediatric relapsed/refractory leukemia. J. Clin. Oncol. 29(24), 3293-3300 (2011).

    2. Ghassabian, S., Gillani, T.B., Rawling, T., et al. Sorafenib N-oxide is an inhibitor of human hepatic CYP3A4. AAPS J. 21(2), 15 (2019).