Sorafenib tosylate
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MedKoo CAT#: 471013

CAS#: 475207-59-1 (tosylate)

Description: Sorafenib, also known as BAY 43-9006, is a synthetic compound targeting growth signaling and angiogenesis. Sorafenib blocks the enzyme RAF kinase, a critical component of the RAF/MEK/ERK signaling pathway that controls cell division and proliferation; in addition, sorafenib inhibits the VEGFR-2/PDGFR-beta signaling cascade, thereby blocking tumor angiogenesis. Sorafenib was approved in 2005 for use in the treatment of advanced renal cancer.


Chemical Structure

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Sorafenib tosylate
CAS# 475207-59-1 (tosylate)

Theoretical Analysis

MedKoo Cat#: 471013
Name: Sorafenib tosylate
CAS#: 475207-59-1 (tosylate)
Chemical Formula: C28H24ClF3N4O6S
Exact Mass:
Molecular Weight: 637.02
Elemental Analysis: C, 52.79; H, 3.80; Cl, 5.56; F, 8.95; N, 8.80; O, 15.07; S, 5.03

Size Price Shipping out time Quantity
1g USD 85 Same day
5g USD 150 Same day
10g USD 240 Same day
20g USD 420 Same day
50g USD 750 Same day
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Pricing updated 2021-03-01. Prices are subject to change without notice.

Sorafenib tosylate, purity > 98%, is in stock. The same day shipping out after order is received.

Related CAS #: 475207-59-1 (tosylate)   284461-73-0 (free base)    

Synonym: BAY 439006; BAY439006; BAY-439006; BAY 439006 Tosylate Salt; BAY 549085; Sorafenib tosylate; Nexavar; SFN.

IUPAC/Chemical Name: 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide 4-methylbenzenesulfonate.

InChi Key: IVDHYUQIDRJSTI-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H16ClF3N4O3.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h2-11H,1H3,(H,26,30)(H2,28,29,31);2-5H,1H3,(H,8,9,10)

SMILES Code: O=C(NC)C1=NC=CC(OC2=CC=C(NC(NC3=CC=C(Cl)C(C(F)(F)F)=C3)=O)C=C2)=C1.O=S(C4=CC=C(C)C=C4)(O)=O

Appearance:
white 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:
Soluble in DMSO, not in water

Shelf Life:
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 637.02 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.

Select a batch to recalculate based on the batch molecular weight:
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

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  1: Davies JM, Dhruva NS, Walko CM, Socinski MA, Bernard S, Hayes DN, Kim WY, Ivanova A, Keller K, Hilbun LR, Chiu M, Dees EC, Stinchcombe TE. A phase I trial of sorafenib combined with cisplatin/etoposide or carboplatin/pemetrexed in refractory solid tumor patients. Lung Cancer. 2010 Jun 24. [Epub ahead of print] PubMed PMID: 20580118.

2: Haubeiss S, Schmid JO, Muerdter TE, Sonnenberg M, Friedel G, van der Kuip H, Aulitzky WE. Dasatinib reverses Cancer-associated Fibroblasts (CAFs) from primary Lung Carcinomas to a Phenotype comparable to that of normal Fibroblasts. Mol Cancer. 2010 Jun 27;9(1):168. [Epub ahead of print] PubMed PMID: 20579391.

3: Siegel AB, Olsen SK, Magun A, Brown RS Jr. Sorafenib: Where do we go from here? Hepatology. 2010 Mar 1;52(1):360-369. [Epub ahead of print] PubMed PMID: 20578152.

4: Kodaira M, Takahashi S, Takeuchi K, Yuasa T, Saotome T, Yonese J, Fukui I, Hatake K. Sorafenib-induced erythema multiforme for metastatic renal cell carcinoma. Ann Oncol. 2010 Jul;21(7):1563-5. PubMed PMID: 20573851.

5: Wörns MA, Galle PR. Future perspectives in hepatocellular carcinoma. Dig Liver Dis. 2010 Jul;42 Suppl 3:S302-9. PubMed PMID: 20547319.

6: Rimassa L, Santoro A. The present and the future landscape of treatment of advanced hepatocellular carcinoma. Dig Liver Dis. 2010 Jul;42 Suppl 3:S273-80. PubMed PMID: 20547314.

7: Lachenmayer A, Alsinet C, Chang CY, Llovet JM. Molecular approaches to treatment of hepatocellular carcinoma. Dig Liver Dis. 2010 Jul;42 Suppl 3:S264-72. PubMed PMID: 20547313.

8: Andreana L, Burroughs AK. Treatment of early hepatocellular carcinoma: How to predict and prevent recurrence. Dig Liver Dis. 2010 Jul;42 Suppl 3:S249-57. PubMed PMID: 20547311.

9: Shao YY, Lin ZZ, Hsu C, Shen YC, Hsu CH, Cheng AL. Early alpha-fetoprotein response predicts treatment efficacy of antiangiogenic systemic therapy in patients with advanced hepatocellular carcinoma. Cancer. 2010 Jun 22. [Epub ahead of print] PubMed PMID: 20572033.

10: Augustine CK, Toshimitsu H, Jung SH, Zipfel PA, Yoo JS, Yoshimoto Y, Selim MA, Burchette J, Beasley GM, McMahon N, Padussis J, Pruitt SK, Ali-Osman F, Tyler DS. Sorafenib, a Multikinase Inhibitor, Enhances the Response of Melanoma to Regional Chemotherapy. Mol Cancer Ther. 2010 Jun 22. [Epub ahead of print] PubMed PMID: 20571072.    



Additional Information

Sorafenib tosylate is a white to yellowish or brownish solid with a molecular formula of C21H16ClF3N4O3 x C7H8O3S and a molecular weight of 637.0 g/mole. Sorafenib tosylate is practically insoluble in aqueous media, slightly soluble in ethanol and soluble in PEG 400. Each red, round NEXAVAR film-coated tablet contains sorafenib tosylate (274 mg) equivalent to 200 mg of sorafenib and the following inactive ingredients:  croscarmellose sodium, microcrystalline cellulose, hypromellose, sodium lauryl sulphate, magnesium stearate, polyethylene glycol, titanium dioxide and ferric oxide red.
 
According to http://en.wikipedia.org/wiki/Sorafenib, S orafenib was approved by the U.S. Food and Drug Administration (FDA) in December 2005, and received European Commission marketing authorization in July 2006, both for use in the treatment of advanced renal cancer. The European Commission granted marketing authorization to the drug for the treatment of patients with hepatocellular carcinoma (HCC), the most common form of liver cancer, in October 2007, and FDA approval for this indication followed in November 2007. In November 2009, the UK's National Institute of Clinical Excellence declined to approve the drug for use within the NHS in England, Wales and Northern Ireland, stating that its effectiveness (increasing survival in primary liver cancer by 6 months) did not justify its high price, at up to £3000 per patient per month. In Scotland the drug had already been refused authorization by the Scottish Medicines Consortium for use within NHS Scotland, for the same reason.
orafenib was approved by the U.S. Food and Drug Administration (FDA) in December 2005, and received European Commission marketing authorization in July 2006, both for use in the treatment of advanced renal cancer. The European Commission granted marketing authorization to the drug for the treatment of patients with hepatocellular carcinoma (HCC), the most common form of liver cancer, in October 2007, and FDA approval for this indication followed in November 2007. In November 2009, the UK's National Institute of Clinical Excellence declined to approve the drug for use within the NHS in England, Wales and Northern Ireland, stating that its effectiveness (increasing survival in primary liver cancer by 6 months) did not justify its high price, at up to £3000 per patient per month. In Scotland the drug had already been refused authorization by the Scottish Medicines Consortium for use within NHS Scotland, for the same reason.
Adverse effects of sorafenib include skin rash, hand-foot skin reactions, diarrhea, and hypertension. A case of diffuse yellow discoloration of the skin has been reported. Sorafenib has also been implicated in the development of reversible posterior leukoencephalopathy syndrome and reversible erythrocytosis..
Adverse effects of sorafenib include skin rash, hand-foot skin reactions, diarrhea, and hypertension. A case of diffuse yellow discoloration of the skin has been reported. Sorafenib has also been implicated in the development of reversible posterior leukoencephalopathy syndrome and reversible erythrocytosis..