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MedKoo Cat#: 205638 | Name: TAK-733
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Description:

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

TAK-733 is an orally bioavailable small-molecule inhibitor of MEK1 and MEK2 (MEK1/2) with potential antineoplastic activity. MEK inhibitor TAK-733 selectively binds to and inhibits the activity of MEK1/2, preventing the activation of MEK1/2-dependent effector proteins and transcription factors, which may result in the inhibition of growth factor-mediated cell signaling and tumor cell proliferation. MEK1/2 (MAP2K1/K2) are dual-specificity threonine/tyrosine kinases that play key roles in the activation of the RAS/RAF/MEK/ERK pathway and are often upregulated in a variety of tumor cell types.

Chemical Structure

TAK-733
TAK-733
CAS#1035555-63-5

Theoretical Analysis

MedKoo Cat#: 205638

Name: TAK-733

CAS#: 1035555-63-5

Chemical Formula: C17H15F2IN4O4

Exact Mass: 504.0106

Molecular Weight: 504.23

Elemental Analysis: C, 40.49; H, 3.00; F, 7.54; I, 25.17; N, 11.11; O, 12.69

Price and Availability

Size Price Availability Quantity
5mg USD 350.00
10mg USD 600.00 2 Weeks
50mg USD 1,300.00 2 Weeks
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Related CAS #
No Data
Synonym
TAK733, TAK 733, TAK733
IUPAC/Chemical Name
(R)-3-(2,3-Dihydroxypropyl)-6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione
InChi Key
RCLQNICOARASSR-SECBINFHSA-N
InChi Code
InChI=1S/C17H15F2IN4O4/c1-23-15-12(16(27)24(7-21-15)5-9(26)6-25)14(13(19)17(23)28)22-11-3-2-8(20)4-10(11)18/h2-4,7,9,22,25-26H,5-6H2,1H3/t9-/m1/s1
SMILES Code
O=C1C(C(NC2=CC=C(I)C=C2F)=C(F)C(N3C)=O)=C3N=CN1C[C@@H](O)CO
Appearance
White to off-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

Preparing Stock Solutions

The following data is based on the product molecular weight 504.23 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
1: Dong Q, Dougan DR, Gong X, Halkowycz P, Jin B, Kanouni T, O'Connell SM, Scorah N, Shi L, Wallace MB, Zhou F. Discovery of TAK-733, a potent and selective MEK allosteric site inhibitor for the treatment of cancer. Bioorg Med Chem Lett. 2011 Mar 1;21(5):1315-9. doi: 10.1016/j.bmcl.2011.01.071. Epub 2011 Jan 22. PMID: 21310613. 2: von Euw E, Atefi M, Attar N, Chu C, Zachariah S, Burgess BL, Mok S, Ng C, Wong DJ, Chmielowski B, Lichter DI, Koya RC, McCannel TA, Izmailova E, Ribas A. Antitumor effects of the investigational selective MEK inhibitor TAK733 against cutaneous and uveal melanoma cell lines. Mol Cancer. 2012 Apr 19;11:22. doi: 10.1186/1476-4598-11-22. PMID: 22515704; PMCID: PMC3444881. 3: Dahlman KB, Xia J, Hutchinson K, Ng C, Hucks D, Jia P, Atefi M, Su Z, Branch S, Lyle PL, Hicks DJ, Bozon V, Glaspy JA, Rosen N, Solit DB, Netterville JL, Vnencak-Jones CL, Sosman JA, Ribas A, Zhao Z, Pao W. BRAF(L597) mutations in melanoma are associated with sensitivity to MEK inhibitors. Cancer Discov. 2012 Sep;2(9):791-7. doi: 10.1158/2159-8290.CD-12-0097. Epub 2012 Jul 13. PMID: 22798288; PMCID: PMC3449158. 4: Garraway LA, Baselga J. Whole-genome sequencing and cancer therapy: is too much ever enough? Cancer Discov. 2012 Sep;2(9):766-8. doi: 10.1158/2159-8290.CD-12-0359. PMID: 22969114. 5: Nakamura A, Arita T, Tsuchiya S, Donelan J, Chouitar J, Carideo E, Galvin K, Okaniwa M, Ishikawa T, Yoshida S. Antitumor activity of the selective pan-RAF inhibitor TAK-632 in BRAF inhibitor-resistant melanoma. Cancer Res. 2013 Dec 1;73(23):7043-55. doi: 10.1158/0008-5472.CAN-13-1825. Epub 2013 Oct 11. PMID: 24121489. 6: Zhang Y, Xue D, Wang X, Lu M, Gao B, Qiao X. Screening of kinase inhibitors targeting BRAF for regulating autophagy based on kinase pathways. Mol Med Rep. 2014 Jan;9(1):83-90. doi: 10.3892/mmr.2013.1781. Epub 2013 Nov 7. PMID: 24213221. 7: Acquaviva J, Smith DL, Jimenez JP, Zhang C, Sequeira M, He S, Sang J, Bates RC, Proia DA. Overcoming acquired BRAF inhibitor resistance in melanoma via targeted inhibition of Hsp90 with ganetespib. Mol Cancer Ther. 2014 Feb;13(2):353-63. doi: 10.1158/1535-7163.MCT-13-0481. Epub 2014 Jan 7. PMID: 24398428. 8: Micel LN, Tentler JJ, Tan AC, Selby HM, Brunkow KL, Robertson KM, Davis SL, Klauck PJ, Pitts TM, Gangolli E, Fabrey R, O'Connell SM, Vincent PW, Eckhardt SG. Antitumor activity of the MEK inhibitor TAK-733 against melanoma cell lines and patient-derived tumor explants. Mol Cancer Ther. 2015 Feb;14(2):317-25. doi: 10.1158/1535-7163.MCT-13-1012. Epub 2014 Nov 5. PMID: 25376610; PMCID: PMC4671492. 9: Ishino S, Miyake H, Vincent P, Mori I. Evaluation of the therapeutic efficacy of a MEK inhibitor (TAK-733) using ¹⁸F-fluorodeoxyglucose-positron emission tomography in the human lung xenograft model A549. Ann Nucl Med. 2015 Aug;29(7):613-20. doi: 10.1007/s12149-015-0984-4. Epub 2015 May 27. PMID: 26014721; PMCID: PMC4526591. 10: Lieu CH, Klauck PJ, Henthorn PK, Tentler JJ, Tan AC, Spreafico A, Selby HM, Britt BC, Bagby SM, Arcaroli JJ, Messersmith WA, Pitts TM, Eckhardt SG. Antitumor activity of a potent MEK inhibitor, TAK-733, against colorectal cancer cell lines and patient derived xenografts. Oncotarget. 2015 Oct 27;6(33):34561-72. doi: 10.18632/oncotarget.5949. PMID: 26439693; PMCID: PMC4741473. 11: Baranski Z, Booij TH, Kuijjer ML, de Jong Y, Cleton-Jansen AM, Price LS, van de Water B, Bovée JV, Hogendoorn PC, Danen EH. MEK inhibition induces apoptosis in osteosarcoma cells with constitutive ERK1/2 phosphorylation. Genes Cancer. 2015 Nov;6(11-12):503-12. doi: 10.18632/genesandcancer.91. PMID: 26807203; PMCID: PMC4701229. 12: de la Puente P, Muz B, Jin A, Azab F, Luderer M, Salama NN, Azab AK. MEK inhibitor, TAK-733 reduces proliferation, affects cell cycle and apoptosis, and synergizes with other targeted therapies in multiple myeloma. Blood Cancer J. 2016 Feb 26;6(2):e399. doi: 10.1038/bcj.2016.7. PMID: 26918363; PMCID: PMC4771970. 13: Kinoshita E, Kinoshita-Kikuta E, Kubota Y, Takekawa M, Koike T. A Phos-tag SDS-PAGE method that effectively uses phosphoproteomic data for profiling the phosphorylation dynamics of MEK1. Proteomics. 2016 Jul;16(13):1825-36. doi: 10.1002/pmic.201500494. Epub 2016 Jun 8. PMID: 27169363. 14: Adjei AA, LoRusso P, Ribas A, Sosman JA, Pavlick A, Dy GK, Zhou X, Gangolli E, Kneissl M, Faucette S, Neuwirth R, Bózon V. A phase I dose-escalation study of TAK-733, an investigational oral MEK inhibitor, in patients with advanced solid tumors. Invest New Drugs. 2017 Feb;35(1):47-58. doi: 10.1007/s10637-016-0391-2. Epub 2016 Sep 21. PMID: 27650277; PMCID: PMC5306265. 15: Peterson BG, Tan KW, Osa-Andrews B, Iram SH. High-content screening of clinically tested anticancer drugs identifies novel inhibitors of human MRP1 (ABCC1). Pharmacol Res. 2017 May;119:313-326. doi: 10.1016/j.phrs.2017.02.024. Epub 2017 Feb 28. PMID: 28258008. 16: Albert EA, Bökel C. A cell based, high throughput assay for quantitative analysis of Hedgehog pathway activation using a Smoothened activation sensor. Sci Rep. 2017 Oct 30;7(1):14341. doi: 10.1038/s41598-017-14767-1. PMID: 29085027; PMCID: PMC5662767. 17: Park JH, Kim SW, Cha MJ, Yoon N, Lee CY, Lee J, Seo HH, Shin S, Choi JW, Lee S, Lim S, Hwang KC. TAK-733 inhibits inflammatory neointimal formation by suppressing proliferation, migration, and inflammation in vitro and in vivo. Exp Mol Med. 2018 Apr 20;50(4):1-12. doi: 10.1038/s12276-018-0052-y. PMID: 29674718; PMCID: PMC5938062. 18: Jasek-Gajda E, Gajda M, Jasińska M, Litwin JA, Lis GJ. TAK-733, a Selective MEK Inhibitor, Enhances Voreloxin-induced Apoptosis in Myeloid Leukemia Cells. Anticancer Res. 2018 Nov;38(11):6147-6156. doi: 10.21873/anticanres.12967. PMID: 30396931. 19: Lee CY, Lee J, Seo HH, Shin S, Kim SW, Lee S, Lim S, Hwang KC. TAK733 attenuates adrenergic receptor-mediated cardiomyocyte hypertrophy via inhibiting ErkThr188 phosphorylation. Clin Hemorheol Microcirc. 2019;72(2):179-187. doi: 10.3233/CH-180476. PMID: 30714951. 20: Anastasov N, Hirmer E, Klenner M, Ott J, Falkenberg N, Bao X, Mutschelknaus L, Moertl S, Combs S, Atkinson MJ, Schmid T. MEK1 Inhibitor Combined with Irradiation Reduces Migration of Breast Cancer Cells Including miR-221 and ZEB1 EMT Marker Expression. Cancers (Basel). 2020 Dec 14;12(12):3760. doi: 10.3390/cancers12123760. PMID: 33327491; PMCID: PMC7764972.