A-484954 | CAS# 142557-61-7 | Biochemical

A-484954
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573979

CAS#: 142557-61-7

Description: A-484954 is an ATP-competitive inhibitor of eukaryotic elongation factor-2 kinase (eEF-2K). It reduces eEF-2K autophosphorylation in PC3, HeLa, H460, H1299, and MDA-MB-231 cancer cells.

Chemical Structure

A-484954

CAS# 142557-61-7

Instruction

Theoretical Analysis

MedKoo Cat#: 573979
Name: A-484954
CAS#: 142557-61-7
Chemical Formula: C13H15N5O3
Exact Mass: 289.12
Molecular Weight: 289.290
Elemental Analysis: C, 53.97; H, 5.23; N, 24.21; O, 16.59

Price and Availability

Size	Price	Availability
5mg	USD 415	2 Weeks
10mg	USD 650	2 Weeks
25mg	USD 1050	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: A-484954

IUPAC/Chemical Name: 7-amino-1-cyclopropyl-3-ethyl-1,2,3,4-tetrahydro-2,4-dioxo-pyrido[2,3-d]pyrimidine-6-carboxamide

InChi Key: HWODCHXORCTEGU-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H15N5O3/c1-2-17-12(20)8-5-7(10(15)19)9(14)16-11(8)18(13(17)21)6-3-4-6/h5-6H,2-4H2,1H3,(H2,14,16)(H2,15,19)

SMILES Code: O=C1N(CC)C(C(C=C(C(N)=O)C(N)=N2)=C2N1C3CC3)=O

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

Shelf Life: >3 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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 289.29 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:
In vitro protocol:
In vivo protocol:

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1: Piserchio A, Isiorho EA, Dalby KN, Ghose R. Structure of the complex between calmodulin and a functional construct of eukaryotic elongation factor 2 kinase bound to an ATP-competitive inhibitor. J Biol Chem. 2023 May 10:104813. doi: 10.1016/j.jbc.2023.104813. Epub ahead of print. PMID: 37172726.

2: Chen Z, Gopalakrishnan SM, Bui MH, Soni NB, Warrior U, Johnson EF, Donnelly JB, Glaser KB. 1-Benzyl-3-cetyl-2-methylimidazolium iodide (NH125) induces phosphorylation of eukaryotic elongation factor-2 (eEF2): a cautionary note on the anticancer mechanism of an eEF2 kinase inhibitor. J Biol Chem. 2011 Dec 23;286(51):43951-43958. doi: 10.1074/jbc.M111.301291. Epub 2011 Oct 21. PMID: 22020937; PMCID: PMC3243513.

3: Usui T, Nijima R, Sakatsume T, Otani K, Kameshima S, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase controls proliferation and migration of vascular smooth muscle cells. Acta Physiol (Oxf). 2015 Feb;213(2):472-80. doi: 10.1111/apha.12354. Epub 2014 Aug 26. PMID: 25069823.

4: Kameshima S, Kazama K, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase mediates monocrotaline-induced pulmonary arterial hypertension via reactive oxygen species-dependent vascular remodeling. Am J Physiol Heart Circ Physiol. 2015 May 15;308(10):H1298-305. doi: 10.1152/ajpheart.00864.2014. Epub 2015 Mar 13. PMID: 25770246.

5: Weng W, Chen Y, Wang M, Zhuang Y, Behnisch T. Potentiation of Schaffer- Collateral CA1 Synaptic Transmission by eEF2K and p38 MAPK Mediated Mechanisms. Front Cell Neurosci. 2016 Oct 25;10:247. doi: 10.3389/fncel.2016.00247. PMID: 27826228; PMCID: PMC5078695.

6: Bender CL, Yang Q, Sun L, Liu SJ. NH125 reduces the level of CPEB3, an RNA binding protein, to promote synaptic GluA2 expression. Neuropharmacology. 2016 Feb;101:531-7. doi: 10.1016/j.neuropharm.2015.03.017. Epub 2015 Apr 2. PMID: 25842244; PMCID: PMC4592363.

7: Wang Q, Edupuganti R, Tavares CD, Dalby KN, Ren P. Using docking and alchemical free energy approach to determine the binding mechanism of eEF2K inhibitors and prioritizing the compound synthesis. Front Mol Biosci. 2015 Mar 19;2:9. doi: 10.3389/fmolb.2015.00009. PMID: 25988177; PMCID: PMC4429643.

8: Edupuganti R, Wang Q, Tavares CD, Chitjian CA, Bachman JL, Ren P, Anslyn EV, Dalby KN. Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-2,4-dione derivatives as eEF-2K inhibitors. Bioorg Med Chem. 2014 Sep 1;22(17):4910-6. doi: 10.1016/j.bmc.2014.06.050. Epub 2014 Jun 30. PMID: 25047940; PMCID: PMC6473179.

9: Klupt KA, Jia Z. eEF2K Inhibitor Design: The Progression of Exemplary Structure-Based Drug Design. Molecules. 2023 Jan 21;28(3):1095. doi: 10.3390/molecules28031095. PMID: 36770760; PMCID: PMC9921739.

10: Kodama T, Okada M, Yamawaki H. Mechanisms underlying the relaxation by A484954, a eukaryotic elongation factor 2 kinase inhibitor, in rat isolated mesenteric artery. J Pharmacol Sci. 2018 May;137(1):86-92. doi: 10.1016/j.jphs.2018.04.006. Epub 2018 May 2. PMID: 29778449.

11: Kodama T, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase inhibitor, A484954 inhibits noradrenaline-induced acute increase of blood pressure in rats. J Vet Med Sci. 2019 Jan 8;81(1):35-41. doi: 10.1292/jvms.18-0606. Epub 2018 Nov 13. PMID: 30429409; PMCID: PMC6361655.

12: Kodama T, Otani K, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase inhibitor, A484954 inhibits perivascular sympathetic nerve stimulation- induced vasoconstriction in isolated renal artery. Eur J Pharmacol. 2022 Jul 5;926:175042. doi: 10.1016/j.ejphar.2022.175042. Epub 2022 May 19. PMID: 35598844.

13: Kodama T, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase inhibitor, A484954 potentiates β-adrenergic receptor agonist-induced acute decrease in diastolic blood pressure in rats. J Vet Med Sci. 2019 Oct 24;81(10):1509-1514. doi: 10.1292/jvms.19-0425. Epub 2019 Sep 5. PMID: 31484844; PMCID: PMC6863711.

14: Kodama T, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase inhibitor, A484954 lowered blood pressure in spontaneously hypertensive rats via inducing vasorelaxation. J Pharmacol Sci. 2020 Nov;144(3):165-171. doi: 10.1016/j.jphs.2020.07.007. Epub 2020 Jul 18. PMID: 32811745.

15: Gladulich LFH, Peixoto-Rodrigues MC, Campello-Costa P, Paes-de-Carvalho R, Cossenza M. NMDA-induced nitric oxide generation and CREB activation in central nervous system is dependent on eukaryotic elongation factor 2 kinase. Biochim Biophys Acta Mol Cell Res. 2020 Oct;1867(10):118783. doi: 10.1016/j.bbamcr.2020.118783. Epub 2020 Jun 20. PMID: 32569665.

16: Kodama T, Kameshima S, Otani K, Okada M, Yamawaki H. Eukaryotic elongation factor 2 kinase inhibitor, A484954 induces diuretic effect via renal vasorelaxation in spontaneously hypertensive rats. Eur J Pharmacol. 2021 Dec 15;913:174637. doi: 10.1016/j.ejphar.2021.174637. Epub 2021 Nov 18. PMID: 34801528.

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