Mubritinib | TAK165 | CAS#366017-09-6

MedKoo Cat#: 206800 | Name: Mubritinib

Description:

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

Mubritinib, also known as TAK-165, is a protein kinase inhibitor which was under development by Takeda for the treatment of cancer. It completed phase I clinical trials (may be discontinued since 2008). Mubritinib(TAK 165) is a potent EGFR, HER2 and p34cdc2 inhibitor with IC50 of 6 nM and 0.2 ÂµM, respectively. Mubritinib(TAK 165) also inhibits p33cdk2 and p33cdk5. Mubritinib(TAK 165) displays > 4000-fold selectivity over EGFR, FGFR, PDGFR, JAK1 and Src. Mubritinib(TAK 165) exhibits potent antiproliferative effects in ErbB2-overexpressing cancer cell lines (IC50 = 5 nM in BT474 breast cancer cells) and significantly inhibits bladder, breast and prostate cancer xenograft growth in vivo. (source: http://en.wikipedia.org/wiki/Mubritinib).

Chemical Structure

Mubritinib

CAS#366017-09-6

Theoretical Analysis

MedKoo Cat#: 206800

Name: Mubritinib

CAS#: 366017-09-6

Chemical Formula: C25H23F3N4O2

Exact Mass: 468.1773

Molecular Weight: 468.47

Elemental Analysis: C, 64.10; H, 4.95; F, 12.17; N, 11.96; O, 6.83

Price and Availability

Size	Price	Availability
50mg	USD 250.00	2 Weeks
100mg	USD 450.00	2 Weeks
200mg	USD 750.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks
5g	USD 8,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Mubritinib; TAK 165; TAK-165; TAK165

IUPAC/Chemical Name

(E)-4-((4-(4-(1H-1,2,3-triazol-1-yl)butyl)phenoxy)methyl)-2-(4-(trifluoromethyl)styryl)oxazole

InChi Key

ZTFBIUXIQYRUNT-MDWZMJQESA-N

InChi Code

InChI=1S/C25H23F3N4O2/c26-25(27,28)21-9-4-20(5-10-21)8-13-24-30-22(18-34-24)17-33-23-11-6-19(7-12-23)3-1-2-15-32-16-14-29-31-32/h4-14,16,18H,1-3,15,17H2/b13-8+

SMILES Code

FC(C1=CC=C(C=C1)/C=C/C2=NC(COC3=CC=C(CCCCN4N=NC=C4)C=C3)=CO2)(F)F

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mubritinib (TAK-165) is a potent and selective EGFR2/HER2 inhibitor with an IC50 of 6 nM.

In vitro activity:

Mubritinib caused PEL cells to undergo cell cycle arrest with accumulation of sub-G1 population and Annexin V. Mubritinib inhibited LANA binding to KSHV terminal repeat (TR) DNA in KSHV+ PEL cells, but did not lead to KSHV lytic cycle reactivation. Seahorse analysis demonstrated that Mubritinib selectively inhibits the maximal oxygen consumption (OCR) in PEL cells and metabolomics revealed changes in ATP/ADP and ATP/AMP ratios. Reference: Oncotarget. 2020 Nov 17;11(46):4224-4242. https://pubmed.ncbi.nlm.nih.gov/33245718/

In vivo activity:

In the mouse xenograft model, treatment with TAK-165 significantly inhibited growth of UMUC-3, ACHN, and LN-REC4. The antitumor effect (T/C [%]=growth of TAK-165 treated tumor/average growth of control tumorx100) after 14 days treatment were 22.9%, 26.0%, and 26.5% in UMUC3, ACHN and LN-REC4, respectively. Reference: Int J Urol. 2006 May;13(5):587-92. https://pubmed.ncbi.nlm.nih.gov/16771730/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	10.67
	DMSO	45.8	97.73

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 468.47 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.

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. Yang X, Ji C, Liu X, Zheng C, Zhang Y, Shen R, Zhou Z. The significance of the neuregulin-1/ErbB signaling pathway and its effect on Sox10 expression in the development of terminally differentiated Schwann cells in vitro. Int J Neurosci. 2022 Feb;132(2):171-180. doi: 10.1080/00207454.2020.1806266. Epub 2020 Aug 24. PMID: 32757877. 2. Calderon A, Soldan SS, De Leo A, Deng Z, Frase DM, Anderson EM, Zhang Y, Vladimirova O, Lu F, Leung JC, Murphy ME, Lieberman PM. Identification of Mubritinib (TAK 165) as an inhibitor of KSHV driven primary effusion lymphoma via disruption of mitochondrial OXPHOS metabolism. Oncotarget. 2020 Nov 17;11(46):4224-4242. doi: 10.18632/oncotarget.27815. PMID: 33245718; PMCID: PMC7679036. 3. Baccelli I, Gareau Y, Lehnertz B, Gingras S, Spinella JF, Corneau S, Mayotte N, Girard S, Frechette M, Blouin-Chagnon V, Leveillé K, Boivin I, MacRae T, Krosl J, Thiollier C, Lavallée VP, Kanshin E, Bertomeu T, Coulombe-Huntington J, St-Denis C, Bordeleau ME, Boucher G, Roux PP, Lemieux S, Tyers M, Thibault P, Hébert J, Marinier A, Sauvageau G. Mubritinib Targets the Electron Transport Chain Complex I and Reveals the Landscape of OXPHOS Dependency in Acute Myeloid Leukemia. Cancer Cell. 2019 Jul 8;36(1):84-99.e8. doi: 10.1016/j.ccell.2019.06.003. PMID: 31287994. 4. Nagasawa J, Mizokami A, Koshida K, Yoshida S, Naito K, Namiki M. Novel HER2 selective tyrosine kinase inhibitor, TAK-165, inhibits bladder, kidney and androgen-independent prostate cancer in vitro and in vivo. Int J Urol. 2006 May;13(5):587-92. doi: 10.1111/j.1442-2042.2006.01342.x. PMID: 16771730.

In vitro protocol:

In vivo protocol:

1. Baccelli I, Gareau Y, Lehnertz B, Gingras S, Spinella JF, Corneau S, Mayotte N, Girard S, Frechette M, Blouin-Chagnon V, Leveillé K, Boivin I, MacRae T, Krosl J, Thiollier C, Lavallée VP, Kanshin E, Bertomeu T, Coulombe-Huntington J, St-Denis C, Bordeleau ME, Boucher G, Roux PP, Lemieux S, Tyers M, Thibault P, Hébert J, Marinier A, Sauvageau G. Mubritinib Targets the Electron Transport Chain Complex I and Reveals the Landscape of OXPHOS Dependency in Acute Myeloid Leukemia. Cancer Cell. 2019 Jul 8;36(1):84-99.e8. doi: 10.1016/j.ccell.2019.06.003. PMID: 31287994. 2. Nagasawa J, Mizokami A, Koshida K, Yoshida S, Naito K, Namiki M. Novel HER2 selective tyrosine kinase inhibitor, TAK-165, inhibits bladder, kidney and androgen-independent prostate cancer in vitro and in vivo. Int J Urol. 2006 May;13(5):587-92. doi: 10.1111/j.1442-2042.2006.01342.x. PMID: 16771730.

1. Hayashi, K.; Masuda, S.; Kimura, H. Impact of biomarker usage on oncology drug development. Journal of Clinical Pharmacy and Therapeutics (2013), 38(1), 62-67. 2. Anastassiadis, Theonie; Deacon, Sean W.; Devarajan, Karthik; Ma, Haiching; Peterson, Jeffrey R.Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity. Nature Biotechnology (2011), 29(11), 1039-1045. 3. Grinshtein, Natalie; Datti, Alessandro; Fujitani, Mayumi; Uehling, David; Prakesch, Michael; Isaac, Methvin; Irwin, Meredith S.; Wrana, Jeffrey L.; Al-Awar, Rima; Kaplan, David R. Small Molecule Kinase Inhibitor Screen Identifies Polo-Like Kinase 1 as a Target for Neuroblastoma Tumor-Initiating Cells. Cancer Research (2011), 71(4), 1385-1395. 4. Nagasawa, Joji; Mizokami, Atsushi; Koshida, Kiyoshi; Yoshida, Sei; Naito, Kenichiro; Namiki, Mikio. Novel HER2 selective tyrosine kinase inhibitor, TAK-165, inhibits bladder, kidney and androgen-independent prostate cancer in vitro and in vivo. International Journal of Urology (2006), 13(5), 587-592. 5. Sugita, Shozo; Kawashima, Hidenori; Tanaka, Tomoaki; Kurisu, Takeshi; Sugimura, Kazunobu; Nakatani, Tatsuya Effect of type I growth factor receptor tyrosine kinase inhibitors on phosphorylation and transactivation activity of the androgen receptor in prostate cancer cells: Ligand-independent activation of the N-terminal domain of the androgen receptor. Oncology Reports (2004), 11(6), 1273-1279.