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MedKoo Cat#: 208439 | Name: Avutometinib potassium

Description:

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

Avutometinib, also known as RO5126766 and CH5126766, is a protein kinase inhibitor specific for the Raf and MEK mitogen-activated protein kinases (MAPKs) with potential anti-neoplastic activity. Raf/MEK dual kinase Inhibitor RO5126766 specifically inhibits the kinase activities of Raf and MEK, resulting in the inhibition of of target gene transcription that promotes malignant transformation of cells. Both Raf and MEK are serine/threonine-specific kinases that respond to extracellular stimuli, such as mitogens, and are involved in the regulation of cellular processes, such as gene expression, mitosis, differentiation, and apoptosis.

Chemical Structure

Avutometinib potassium
Avutometinib potassium
CAS#946128-90-1 (potassium)

Theoretical Analysis

MedKoo Cat#: 208439

Name: Avutometinib potassium

CAS#: 946128-90-1 (potassium)

Chemical Formula: C21H17FKN5O5S

Exact Mass: 509.0571

Molecular Weight: 509.55

Elemental Analysis: C, 49.50; H, 3.36; F, 3.73; K, 7.67; N, 13.74; O, 15.70; S, 6.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
946128-90-1 (potassium) 946128-88-7 (free) 946128-89-8 (sodium)
Synonym
Avutometinib-potassium, VS-6766; VS 6766; VS-6766; Avutometinib; RO5126766; RO 5126766; RO5126766; CH5126766; CH5126766; CH 5126766.
IUPAC/Chemical Name
Potassium [3-fluoro-4-[(4-methyl-2-oxo-7-pyrimidin-2-yloxychromen-3-yl)methyl]pyridin-2-yl]-(methylsulfamoyl)azanide
InChi Key
KYKJFDDJHVJFIF-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H17FN5O5S.K/c1-12-15-5-4-14(31-21-25-7-3-8-26-21)11-17(15)32-20(28)16(12)10-13-6-9-24-19(18(13)22)27-33(29,30)23-2;/h3-9,11,23H,10H2,1-2H3;/q-1;+1
SMILES Code
O=S([N-]C1=NC=CC(CC(C2=O)=C(C)C3=C(O2)C=C(OC4=NC=CC=N4)C=C3)=C1F)(NC)=O.[K+]
Appearance
To be determined
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
>2 years if stored properly
Drug Formulation
To be determined
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 509.55 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: Qamar F, Sharif Z, Idrees J, Wasim A, Haider S, Salman S. SARS-CoV-2-induced phosphorylation and its pharmacotherapy backed by artificial intelligence and machine learning. Future Sci OA. 2024 May 15;10(1):FSO917. doi: 10.2144/fsoa-2023-0112. PMID: 38827795; PMCID: PMC11140666. 2: Yoshimura A, Horinaka M, Yaoi T, Ono H, Itoh K, Yamada T, Takayama K, Sakai T. Epithelial-mesenchymal transition status is a remarkable biomarker for the combination treatment with avutometinib and defactinib in KRAS-mutated non-small cell lung cancer. Br J Cancer. 2024 May 31. doi: 10.1038/s41416-024-02727-2. Epub ahead of print. PMID: 38822146. 3: Sakai T. "RB-reactivator screening" as a novel cell-based assay for discoveries of molecular targeting agents including the first-in-class MEK inhibitor trametinib (trade name: Mekinist). Pharmacol Ther. 2022 Aug;236:108234. doi: 10.1016/j.pharmthera.2022.108234. Epub 2022 Jun 19. PMID: 35732246. 4: Roskoski R Jr. Blockade of mutant RAS oncogenic signaling with a special emphasis on KRAS. Pharmacol Res. 2021 Oct;172:105806. doi: 10.1016/j.phrs.2021.105806. Epub 2021 Aug 24. PMID: 34450320. 5: Tomida A, Yagyu S, Nakamura K, Kubo H, Yamashima K, Nakazawa Y, Hosoi H, Iehara T. Inhibition of MEK pathway enhances the antitumor efficacy of chimeric antigen receptor T cells against neuroblastoma. Cancer Sci. 2021 Oct;112(10):4026-4036. doi: 10.1111/cas.15074. Epub 2021 Aug 24. PMID: 34382720; PMCID: PMC8486218. 6: Ono H, Horinaka M, Sukeno M, Morita M, Yasuda S, Nishimoto E, Konishi E, Sakai T. Novel RAF/MEK inhibitor CH5126766/VS-6766 has efficacy in combination with eribulin for the treatment of triple-negative breast cancer. Cancer Sci. 2021 Oct;112(10):4166-4175. doi: 10.1111/cas.15071. Epub 2021 Aug 1. PMID: 34288272; PMCID: PMC8486178. 7: Dual RAF-MEK Inhibitor Assessed. Cancer Discov. 2021 Jan;11(1):5-6. doi: 10.1158/2159-8290.CD-NB2020-101. Epub 2020 Nov 13. PMID: 33188055. 8: Guo C, Chénard-Poirier M, Roda D, de Miguel M, Harris SJ, Candilejo IM, Sriskandarajah P, Xu W, Scaranti M, Constantinidou A, King J, Parmar M, Turner AJ, Carreira S, Riisnaes R, Finneran L, Hall E, Ishikawa Y, Nakai K, Tunariu N, Basu B, Kaiser M, Lopez JS, Minchom A, de Bono JS, Banerji U. Intermittent schedules of the oral RAF-MEK inhibitor CH5126766/VS-6766 in patients with RAS/RAF-mutant solid tumours and multiple myeloma: a single-centre, open-label, phase 1 dose-escalation and basket dose-expansion study. Lancet Oncol. 2020 Nov;21(11):1478-1488. doi: 10.1016/S1470-2045(20)30464-2. Epub 2020 Oct 28. Erratum in: Lancet Oncol. 2021 Feb;22(2):e42. doi: 10.1016/S1470-2045(21)00014-0. PMID: 33128873. 9: Acar A, Nichol D, Fernandez-Mateos J, Cresswell GD, Barozzi I, Hong SP, Trahearn N, Spiteri I, Stubbs M, Burke R, Stewart A, Caravagna G, Werner B, Vlachogiannis G, Maley CC, Magnani L, Valeri N, Banerji U, Sottoriva A. Exploiting evolutionary steering to induce collateral drug sensitivity in cancer. Nat Commun. 2020 Apr 21;11(1):1923. doi: 10.1038/s41467-020-15596-z. PMID: 32317663; PMCID: PMC7174377. 10: Wang C, Xi D, Wang H, Niu Y, Liang L, Xu F, Peng Y, Xu P. Hybrids of MEK inhibitor and NO donor as multitarget antitumor drugs. Eur J Med Chem. 2020 Jun 15;196:112271. doi: 10.1016/j.ejmech.2020.112271. Epub 2020 Apr 9. PMID: 32305784. 11: Umemura S, Sowa Y, Iizumi Y, Kitawaki J, Sakai T. Synergistic effect of the inhibitors of RAF/MEK and AXL on KRAS-mutated ovarian cancer cells with high AXL expression. Cancer Sci. 2020 Jun;111(6):2052-2061. doi: 10.1111/cas.14414. Epub 2020 May 17. PMID: 32291856; PMCID: PMC7293078. 12: Nakagawa N, Kikuchi K, Yagyu S, Miyachi M, Iehara T, Tajiri T, Sakai T, Hosoi H. Mutations in the RAS pathway as potential precision medicine targets in treatment of rhabdomyosarcoma. Biochem Biophys Res Commun. 2019 May 7;512(3):524-530. doi: 10.1016/j.bbrc.2019.03.038. Epub 2019 Mar 21. PMID: 30904164. 13: Takeuchi Y, Tanaka T, Higashi M, Fumino S, Iehara T, Hosoi H, Sakai T, Tajiri T. In vivo effects of short- and long-term MAPK pathway inhibition against neuroblastoma. J Pediatr Surg. 2018 Dec;53(12):2454-2459. doi: 10.1016/j.jpedsurg.2018.08.026. Epub 2018 Sep 1. PMID: 30266481. 14: Knauf JA, Luckett KA, Chen KY, Voza F, Socci ND, Ghossein R, Fagin JA. Hgf/Met activation mediates resistance to BRAF inhibition in murine anaplastic thyroid cancers. J Clin Invest. 2018 Aug 31;128(9):4086-4097. doi: 10.1172/JCI120966. Epub 2018 Aug 20. PMID: 29990309; PMCID: PMC6118575. 15: Bhatt MH, Prajapati CK, Reddy MN. In silico docking studies of Lupeol with MAPK pathway proteins- Raf-1, MEK & ERK. J Exp Ther Oncol. 2017 Nov;12(2):137-140. PMID: 29161781. 16: Tanaka T, Higashi M, Kimura K, Wakao J, Fumino S, Iehara T, Hosoi H, Sakai T, Tajiri T. MEK inhibitors as a novel therapy for neuroblastoma: Their in vitro effects and predicting their efficacy. J Pediatr Surg. 2016 Dec;51(12):2074-2079. doi: 10.1016/j.jpedsurg.2016.09.043. Epub 2016 Sep 16. PMID: 27686482. 17: Ueyama A, Ban N, Fukazawa M, Hirayama T, Takeda M, Yata T, Muramatsu H, Hoshino M, Yamamoto M, Matsuo M, Kawashima Y, Iwase T, Kitazawa T, Kushima Y, Yamada Y, Kawabe Y. Inhibition of MEK1 Signaling Pathway in the Liver Ameliorates Insulin Resistance. J Diabetes Res. 2016;2016:8264830. doi: 10.1155/2016/8264830. Epub 2015 Dec 28. PMID: 26839898; PMCID: PMC4709921. 18: Van Dort ME, Galbán S, Wang H, Sebolt-Leopold J, Whitehead C, Hong H, Rehemtulla A, Ross BD. Dual inhibition of allosteric mitogen-activated protein kinase (MEK) and phosphatidylinositol 3-kinase (PI3K) oncogenic targets with a bifunctional inhibitor. Bioorg Med Chem. 2015 Apr 1;23(7):1386-94. doi: 10.1016/j.bmc.2015.02.053. Epub 2015 Mar 6. PMID: 25766633; PMCID: PMC4370322. 19: Wada M, Horinaka M, Yamazaki T, Katoh N, Sakai T. The dual RAF/MEK inhibitor CH5126766/RO5126766 may be a potential therapy for RAS-mutated tumor cells. PLoS One. 2014 Nov 25;9(11):e113217. doi: 10.1371/journal.pone.0113217. PMID: 25422890; PMCID: PMC4244135. 20: Aoki T, Hyohdoh I, Furuichi N, Ozawa S, Watanabe F, Matsushita M, Sakaitani M, Morikami K, Takanashi K, Harada N, Tomii Y, Shiraki K, Furumoto K, Tabo M, Yoshinari K, Ori K, Aoki Y, Shimma N, Iikura H. Optimizing the Physicochemical Properties of Raf/MEK Inhibitors by Nitrogen Scanning. ACS Med Chem Lett. 2014 Jan 22;5(4):309-14. doi: 10.1021/ml400379x. PMID: 24900832; PMCID: PMC4027752.

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