Eleclazine | CAS#1443211-72-0 | sodium current inhibitor

MedKoo Cat#: 319545 | Name: Eleclazine free base

Description:

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

Eleclazine, also known as GS-6615, is a selective late sodium current inhibitor. Eleclazine is potentially useful for treatment of coronary vasodilators, antiarrhythmics and vasodilators. Eleclazin showed a shortening of the QTc interval (the time interval between the start of the Q-wave and end of the T-wave in the heart’s electrical cycle) in patients with long QT-3 (LQT3) syndrome. LQT3 is a genetic disorder that prolongs the heart’s QTc interval and can cause life-threatening cardiac arrhythmias (abnormal heartbeats).

Chemical Structure

Eleclazine free base

CAS#1443211-72-0 (free base)

Theoretical Analysis

MedKoo Cat#: 319545

Name: Eleclazine free base

CAS#: 1443211-72-0 (free base)

Chemical Formula: C21H16F3N3O3

Exact Mass: 415.1144

Molecular Weight: 415.37

Elemental Analysis: C, 60.72; H, 3.88; F, 13.72; N, 10.12; O, 11.56

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,650.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

1443211-72-0 (free base) 1448754-43-5 (HCl)

Synonym

GS-6615; GS 6615; GS6615; Eleclazine.

IUPAC/Chemical Name

4-[(pyrimidin-2-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]- 3,4-dihydro-1,4-benzoxazepin-5(2H)-one

InChi Key

YNUAEEJQYHYLMS-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H16F3N3O3/c22-21(23,24)30-16-5-2-14(3-6-16)15-4-7-18-17(12-15)20(28)27(10-11-29-18)13-19-25-8-1-9-26-19/h1-9,12H,10-11,13H2

SMILES Code

O=C1N(CC2=NC=CC=N2)CCOC3=CC=C(C4=CC=C(OC(F)(F)F)C=C4)C=C13

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).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 415.37 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

1: El-Bizri N, Xie C, Liu L, Limberis J, Krause M, Hirakawa R, Nguyen S, Tabuena DR, Belardinelli L, Kahlig KM. Eleclazine exhibits enhanced selectivity for long QT syndrome type 3-associated late Na+ current. Heart Rhythm. 2018 Feb;15(2):277-286. doi: 10.1016/j.hrthm.2017.09.028. Epub 2017 Oct 7. PMID: 29017927. 2: Potet F, Egecioglu DE, Burridge PW, George AL Jr. GS-967 and Eleclazine Block Sodium Channels in Human Induced Pluripotent Stem Cell-Derived Cardiomyocytes. Mol Pharmacol. 2020 Nov;98(5):540-547. doi: 10.1124/molpharm.120.000048. Epub 2020 Sep 16. PMID: 32938719. 3: Fuller H, Justo F, Nearing BD, Kahlig KM, Rajamani S, Belardinelli L, Verrier RL. Eleclazine, a new selective cardiac late sodium current inhibitor, confers concurrent protection against autonomically induced atrial premature beats, repolarization alternans and heterogeneity, and atrial fibrillation in an intact porcine model. Heart Rhythm. 2016 Aug;13(8):1679-86. doi: 10.1016/j.hrthm.2016.04.015. Epub 2016 Apr 21. PMID: 27108587. 4: Bacic D, Carneiro JS, Bento AA, Nearing BD, Rajamani S, Belardinelli L, Verrier RL. Eleclazine, an inhibitor of the cardiac late sodium current, is superior to flecainide in suppressing catecholamine-induced ventricular tachycardia and T-wave alternans in an intact porcine model. Heart Rhythm. 2017 Mar;14(3):448-454. doi: 10.1016/j.hrthm.2016.10.021. Epub 2016 Oct 21. PMID: 27777148. 5: Caves RE, Carpenter A, Choisy SC, Clennell B, Cheng H, McNiff C, Mann B, Milnes JT, Hancox JC, James AF. Inhibition of voltage-gated Na+ currents by eleclazine in rat atrial and ventricular myocytes. Heart Rhythm O2. 2020 Aug;1(3):206-214. doi: 10.1016/j.hroo.2020.05.006. PMID: 32864638; PMCID: PMC7442036. 6: Silva AF, Bonatti R, Batatinha JA, Nearing BD, Zeng D, Belardinelli L, Verrier RL. The Selective Late Sodium Current Inhibitor Eleclazine, Unlike Amiodarone, Does Not Alter Defibrillation Threshold or Dominant Frequency of Ventricular Fibrillation. J Cardiovasc Pharmacol. 2017 Mar;69(3):178-182. doi: 10.1097/FJC.0000000000000455. PMID: 28045761. 7: Justo F, Fuller H, Nearing BD, Rajamani S, Belardinelli L, Verrier RL. Inhibition of the cardiac late sodium current with eleclazine protects against ischemia-induced vulnerability to atrial fibrillation and reduces atrial and ventricular repolarization abnormalities in the absence and presence of concurrent adrenergic stimulation. Heart Rhythm. 2016 Sep;13(9):1860-7. doi: 10.1016/j.hrthm.2016.06.020. Epub 2016 Jun 16. PMID: 27317981. 8: Rajamani S, Liu G, El-Bizri N, Guo D, Li C, Chen XL, Kahlig KM, Mollova N, Elzein E, Zablocki J, Belardinelli L. The novel late Na+ current inhibitor, GS-6615 (eleclazine) and its anti-arrhythmic effects in rabbit isolated heart preparations. Br J Pharmacol. 2016 Nov;173(21):3088-3098. doi: 10.1111/bph.13563. Epub 2016 Sep 14. PMID: 27449698; PMCID: PMC5056228. 9: Cheng H, Charles I, James AF, Abdala AP, Hancox JC. Delayed Ventricular Repolarization and Sodium Channel Current Modification in a Mouse Model of Rett Syndrome. Int J Mol Sci. 2022 May 20;23(10):5735. doi: 10.3390/ijms23105735. PMID: 35628543; PMCID: PMC9147596. 10: Wei XH, Yu SD, Ren L, Huang SH, Yang QM, Wang P, Chu YP, Yang W, Ding YS, Huo Y, Wu L. Inhibition of late sodium current suppresses calcium-related ventricular arrhythmias by reducing the phosphorylation of CaMK-II and sodium channel expressions. Sci Rep. 2017 Apr 20;7(1):981. doi: 10.1038/s41598-017-01056-0. PMID: 28428622; PMCID: PMC5430524. 11: Cheng H, Charles I, James AF, Abdala AP, Hancox JC. QTc interval and ventricular action potential prolongation in the Mecp2Null/+ murine model of Rett syndrome. Physiol Rep. 2022 Oct;10(19):e15437. doi: 10.14814/phy2.15437. PMID: 36200140; PMCID: PMC9535259. 12: Chu Y, Yang Q, Ren L, Yu S, Liu Z, Chen Y, Wei X, Huang S, Song L, Zhang P, Ma J, Wu L. Late Sodium Current in Atrial Cardiomyocytes Contributes to the Induced and Spontaneous Atrial Fibrillation in Rabbit Hearts. J Cardiovasc Pharmacol. 2020 Oct;76(4):437-444. doi: 10.1097/FJC.0000000000000883. PMID: 32675747. 13: Zhang Y, Wang HM, Wang YZ, Zhang YY, Jin XX, Zhao Y, Wang J, Sun YL, Xue GL, Li PH, Huang QH, Yang BF, Pan ZW. Increment of late sodium currents in the left atrial myocytes and its potential contribution to increased susceptibility of atrial fibrillation in castrated male mice. Heart Rhythm. 2017 Jul;14(7):1073-1080. doi: 10.1016/j.hrthm.2017.01.046. Epub 2017 Feb 6. PMID: 28185917. 14: Zhang Q, Ma JH, Li H, Wei XH, Zheng J, Li G, Wang CY, Wu Y, He QH, Wu L. Increase in CO2 levels by upregulating late sodium current is proarrhythmic in the heart. Heart Rhythm. 2019 Jul;16(7):1098-1106. doi: 10.1016/j.hrthm.2019.01.029. Epub 2019 Jan 31. PMID: 30710739. 15: Liu X, Ren L, Yu S, Li G, He P, Yang Q, Wei X, Thai PN, Wu L, Huo Y. Late sodium current in synergism with Ca2+/calmodulin-dependent protein kinase II contributes to β-adrenergic activation-induced atrial fibrillation. Philos Trans R Soc Lond B Biol Sci. 2023 Jun 19;378(1879):20220163. doi: 10.1098/rstb.2022.0163. Epub 2023 May 1. PMID: 37122215; PMCID: PMC10150221. 16: Zablocki JA, Elzein E, Li X, Koltun DO, Parkhill EQ, Kobayashi T, Martinez R, Corkey B, Jiang H, Perry T, Kalla R, Notte GT, Saunders O, Graupe M, Lu Y, Venkataramani C, Guerrero J, Perry J, Osier M, Strickley R, Liu G, Wang WQ, Hu L, Li XJ, El-Bizri N, Hirakawa R, Kahlig K, Xie C, Li CH, Dhalla AK, Rajamani S, Mollova N, Soohoo D, Lepist EI, Murray B, Rhodes G, Belardinelli L, Desai MC. Discovery of Dihydrobenzoxazepinone (GS-6615) Late Sodium Current Inhibitor (Late INai), a Phase II Agent with Demonstrated Preclinical Anti- Ischemic and Antiarrhythmic Properties. J Med Chem. 2016 Oct 13;59(19):9005-9017. doi: 10.1021/acs.jmedchem.6b00939. Epub 2016 Oct 3. PMID: 27690427.

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