SB-590885
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406109

CAS#: 40554-55-4

Description: SB-590885 is a novel triarylimidazole that selectively inhibits Raf kinases with more potency towards B-Raf than c-Raf. SB-590885 stabilizes the oncogenic B-Raf kinase domain in an active configuration, which is distinct from the previously reported mechanism of action of the multi-kinase inhibitor, BAY43-9006. Malignant cells expressing oncogenic B-Raf show selective inhibition of mitogen-activated protein kinase activation, proliferation, transformation, and tumorigenicity when exposed to SB-590885 , whereas other cancer cell lines and normal cells display variable sensitivities or resistance to similar treatment.


Price and Availability

Size
Price

5mg
USD 235
Size
Price

10mg
USD 385
Size
Price

SB-590885, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406109
Name: SB-590885
CAS#: 40554-55-4
Chemical Formula: C27H27N5O2
Exact Mass: 453.21648
Molecular Weight: 453.54
Elemental Analysis: C, 71.50; H, 6.00; N, 15.44; O, 7.06


Synonym: SB590885; SB590885; SB 590885

IUPAC/Chemical Name: (E)-5-(2-(4-(2-(dimethylamino)ethoxy)phenyl)-5-(pyridin-4-yl)-1H-imidazol-4-yl)-2,3-dihydro-1H-inden-1-one oxime

InChi Key: MLSAQOINCGAULQ-QFMPWRQOSA-N

InChi Code: InChI=1S/C27H27N5O2/c1-32(2)15-16-34-22-7-3-19(4-8-22)27-29-25(18-11-13-28-14-12-18)26(30-27)21-5-9-23-20(17-21)6-10-24(23)31-33/h3-5,7-9,11-14,17,33H,6,10,15-16H2,1-2H3,(H,29,30)/b31-24+

SMILES Code: CN(CCOC1=CC=C(C2=NC(C3=CC4=C(/C(CC4)=N/O)C=C3)=C(C5=CC=NC=C5)N2)C=C1)C


Technical Data

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:
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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Wang X, Salaski EJ, Berger DM, Powell D, Hu Y, Wojciechowicz D, Collins K, Frommer E. Structure-based design of isoindoline-1,3-diones and 2,3-dihydrophthalazine-1,4-diones as novel B-Raf inhibitors. Bioorg Med Chem Lett. 2011 Dec 1;21(23):6941-4. doi: 10.1016/j.bmcl.2011.10.012. Epub 2011 Oct 12. PubMed PMID: 22024030.

2: Klein RM, Higgins PJ. A switch in RND3-RHOA signaling is critical for melanoma cell invasion following mutant-BRAF inhibition. Mol Cancer. 2011 Sep 14;10:114. doi: 10.1186/1476-4598-10-114. PubMed PMID: 21917148; PubMed Central PMCID: PMC3180434.

3: Park H, Choi H, Hong S, Hong S. Identification of novel BRAF kinase inhibitors with structure-based virtual screening. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5753-6. doi: 10.1016/j.bmcl.2011.08.010. Epub 2011 Aug 8. PubMed PMID: 21873050.

4: Ahnstedt H, Säveland H, Nilsson O, Edvinsson L. Human cerebrovascular contractile receptors are upregulated via a B-Raf/MEK/ERK-sensitive signaling pathway. BMC Neurosci. 2011 Jan 11;12:5. doi: 10.1186/1471-2202-12-5. PubMed PMID: 21223556; PubMed Central PMCID: PMC3023719.

5: Villanueva J, Vultur A, Lee JT, Somasundaram R, Fukunaga-Kalabis M, Cipolla AK, Wubbenhorst B, Xu X, Gimotty PA, Kee D, Santiago-Walker AE, Letrero R, D'Andrea K, Pushparajan A, Hayden JE, Brown KD, Laquerre S, McArthur GA, Sosman JA, Nathanson KL, Herlyn M. Acquired resistance to BRAF inhibitors mediated by a RAF kinase switch in melanoma can be overcome by cotargeting MEK and IGF-1R/PI3K. Cancer Cell. 2010 Dec 14;18(6):683-95. doi: 10.1016/j.ccr.2010.11.023. PubMed PMID: 21156289; PubMed Central PMCID: PMC3026446.

6: Smalley KS, Lioni M, Dalla Palma M, Xiao M, Desai B, Egyhazi S, Hansson J, Wu H, King AJ, Van Belle P, Elder DE, Flaherty KT, Herlyn M, Nathanson KL. Increased cyclin D1 expression can mediate BRAF inhibitor resistance in BRAF V600E-mutated melanomas. Mol Cancer Ther. 2008 Sep;7(9):2876-83. doi: 10.1158/1535-7163.MCT-08-0431. PubMed PMID: 18790768; PubMed Central PMCID: PMC2651569.

7: Takle AK, Bamford MJ, Davies S, Davis RP, Dean DK, Gaiba A, Irving EA, King FD, Naylor A, Parr CA, Ray AM, Reith AD, Smith BB, Staton PC, Steadman JG, Stean TO, Wilson DM. The identification of potent, selective and CNS penetrant furan-based inhibitors of B-Raf kinase. Bioorg Med Chem Lett. 2008 Aug 1;18(15):4373-6. doi: 10.1016/j.bmcl.2008.06.070. Epub 2008 Jun 24. PubMed PMID: 18621524.

8: Senawong T, Phuchareon J, Ohara O, McCormick F, Rauen KA, Tetsu O. Germline mutations of MEK in cardio-facio-cutaneous syndrome are sensitive to MEK and RAF inhibition: implications for therapeutic options. Hum Mol Genet. 2008 Feb 1;17(3):419-30. Epub 2007 Nov 2. PubMed PMID: 17981815.

9: Li N, Batt D, Warmuth M. B-Raf kinase inhibitors for cancer treatment. Curr Opin Investig Drugs. 2007 Jun;8(6):452-6. Review. PubMed PMID: 17621874.

10: King AJ, Patrick DR, Batorsky RS, Ho ML, Do HT, Zhang SY, Kumar R, Rusnak DW, Takle AK, Wilson DM, Hugger E, Wang L, Karreth F, Lougheed JC, Lee J, Chau D, Stout TJ, May EW, Rominger CM, Schaber MD, Luo L, Lakdawala AS, Adams JL, Contractor RG, Smalley KS, Herlyn M, Morrissey MM, Tuveson DA, Huang PS. Demonstration of a genetic therapeutic index for tumors expressing oncogenic BRAF by the kinase inhibitor SB-590885. Cancer Res. 2006 Dec 1;66(23):11100-5. PubMed PMID: 17145850.

11: Takle AK, Brown MJ, Davies S, Dean DK, Francis G, Gaiba A, Hird AW, King FD, Lovell PJ, Naylor A, Reith AD, Steadman JG, Wilson DM. The identification of potent and selective imidazole-based inhibitors of B-Raf kinase. Bioorg Med Chem Lett. 2006 Jan 15;16(2):378-81. Epub 2005 Nov 2. PubMed PMID: 16260133.