MedKoo Cat#: 574205 | Name: Sorafenib N-oxide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sorafenib N-oxide is an active metabolite of sorafenib (BAY 43-9006), an inhibitor of Raf-1, B-RAF, and receptor tyrosine kinases. Sorafenib N-oxide inhibits FLT3 that contains the internal tandem duplication mutation (FLT3-ITD) and inhibits proliferation of MV4-11 acute myeloid leukemia (AML) cells expressing FLT3-ITD. It is selective for AML cell lines containing FLT3-ITD over lines containing wild-type FLT3. Sorafenib N-oxide is also a linear-mixed inhibitor of the cytochrome P450 (CYP) isoform CYP3A4.

Chemical Structure

Sorafenib N-oxide
Sorafenib N-oxide
CAS#583840-03-3 (N-oxide)

Theoretical Analysis

MedKoo Cat#: 574205

Name: Sorafenib N-oxide

CAS#: 583840-03-3 (N-oxide)

Chemical Formula: C21H16ClF3N4O4

Exact Mass: 480.0812

Molecular Weight: 480.83

Elemental Analysis: C, 52.46; H, 3.35; Cl, 7.37; F, 11.85; N, 11.65; O, 13.31

Price and Availability

Size Price Availability Quantity
1mg USD 340.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
284461-73-0 (free base); 475207-59-1 (tosylate)
Synonym
BAY 67-3472, BAY67-3472, BAY 673472; BAY673472; Sorafenib N-oxide
IUPAC/Chemical Name
4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-2-pyridinecarboxamide, 1-oxide
InChi Key
BQAZCCVUZDIZDC-UHFFFAOYSA-N
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)
SMILES Code
ClC1=C(C(F)(F)F)C=C(NC(NC2=CC=C(OC(C=C3C(NC)=O)=CC=[N]3=O)C=C2)=O)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Sorafenib is an Raf inhibitor with IC50s of 6 nM and 20 nM for Raf-1 and B-Raf, respectively.
In vitro activity:
Sorafenib has a role in countering immune-related tumor changes in hepatocellular carcinoma (HCC) therapy. In vitro, sorafenib abolished polarized macrophage-induced epithelial mesenchymal transition and migration of hepatocellular carcinoma cells but not normal hepatocytes. Additionally, sorafenib abolished the polarized macrophage-induced activation of the HGF receptor Met in hepatocellular carcinoma cells. Reference: Oncotarget. 2016 Jun 21;7(25):38292-38305. https://pubmed.ncbi.nlm.nih.gov/27203677/
In vivo activity:
Sorafenib has potential as an antineoplastic agent beyond HCC treatment. In a rat model of hepatocarcinogen exposure, sorafenib reduced neoplastic changes in the liver, decreased liver size, and suppressed proliferation markers like cyclin D1 and β-catenin gene expression. It also decreased levels of glutathione and Bcl-2, suggesting an apoptotic effect. Reference: Clin Exp Med. 2017 May;17(2):185-191. https://pubmed.ncbi.nlm.nih.gov/27085325/

Preparing Stock Solutions

The following data is based on the product molecular weight 480.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chen F, Jiang J, Liu D, Li H, Dong L, Song Y, Zhang Y, Wang J, Qin Y, Zhao G. The lncRNA lnc-TSI antagonizes sorafenib resistance in hepatocellular carcinoma via downregulating miR-4726-5p expression and upregulating KCNMA1 expression. J Mol Histol. 2024 Feb;55(1):83-96. doi: 10.1007/s10735-023-10173-2. Epub 2024 Jan 2. PMID: 38165571. 2. Deng YR, Liu WB, Lian ZX, Li X, Hou X. Sorafenib inhibits macrophage-mediated epithelial-mesenchymal transition in hepatocellular carcinoma. Oncotarget. 2016 Jun 21;7(25):38292-38305. doi: 10.18632/oncotarget.9438. PMID: 27203677; PMCID: PMC5122390. 3. El-Ashmawy NE, Khedr EG, El-Bahrawy HA, Abd El-Fattah EE. Sorafenib effect on liver neoplastic changes in rats: more than a kinase inhibitor. Clin Exp Med. 2017 May;17(2):185-191. doi: 10.1007/s10238-016-0416-3. Epub 2016 Apr 16. PMID: 27085325. 4. Wang ZZ, Liu F, Gong YF, Huang TY, Zhang XM, Huang XY. Antiarthritic Effects of Sorafenib in Rats with Adjuvant-Induced Arthritis. Anat Rec (Hoboken). 2018 Sep;301(9):1519-1526. doi: 10.1002/ar.23856. Epub 2018 Jul 10. PMID: 29752865.
In vitro protocol:
1. Chen F, Jiang J, Liu D, Li H, Dong L, Song Y, Zhang Y, Wang J, Qin Y, Zhao G. The lncRNA lnc-TSI antagonizes sorafenib resistance in hepatocellular carcinoma via downregulating miR-4726-5p expression and upregulating KCNMA1 expression. J Mol Histol. 2024 Feb;55(1):83-96. doi: 10.1007/s10735-023-10173-2. Epub 2024 Jan 2. PMID: 38165571. 2. Deng YR, Liu WB, Lian ZX, Li X, Hou X. Sorafenib inhibits macrophage-mediated epithelial-mesenchymal transition in hepatocellular carcinoma. Oncotarget. 2016 Jun 21;7(25):38292-38305. doi: 10.18632/oncotarget.9438. PMID: 27203677; PMCID: PMC5122390.
In vivo protocol:
1. El-Ashmawy NE, Khedr EG, El-Bahrawy HA, Abd El-Fattah EE. Sorafenib effect on liver neoplastic changes in rats: more than a kinase inhibitor. Clin Exp Med. 2017 May;17(2):185-191. doi: 10.1007/s10238-016-0416-3. Epub 2016 Apr 16. PMID: 27085325. 2. Wang ZZ, Liu F, Gong YF, Huang TY, Zhang XM, Huang XY. Antiarthritic Effects of Sorafenib in Rats with Adjuvant-Induced Arthritis. Anat Rec (Hoboken). 2018 Sep;301(9):1519-1526. doi: 10.1002/ar.23856. Epub 2018 Jul 10. PMID: 29752865.
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).