Eleclazine HCl
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MedKoo CAT#: 563723

CAS#: 1448754-43-5 (HCl)

Description: Eleclazine HCl is a novel late Na+ current inhibitor.

Chemical Structure

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Eleclazine HCl
CAS# 1448754-43-5 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 563723
Name: Eleclazine HCl
CAS#: 1448754-43-5 (HCl)
Chemical Formula: C21H17ClF3N3O3
Exact Mass: 0.00
Molecular Weight: 451.830
Elemental Analysis: C, 55.82; H, 3.79; Cl, 7.85; F, 12.61; N, 9.30; O, 10.62

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10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3650 Ready to ship
2g USD 6450 Ready to ship
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Related CAS #: 1443211-72-0 (free base)   1448754-43-5 (HCl)    

Synonym: Eleclazine Hydrochloride; Eleclazine HCl; GS-6615; GS 6615; GS6615;

IUPAC/Chemical Name: 4-(pyrimidin-2-ylmethyl)-7-(4-(trifluoromethoxy)phenyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one hydrochloride

InChi Key: ZRYHNOXHGYUHFF-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H16F3N3O3.ClH/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;1H

SMILES Code: O=C1N(CC2=NC=CC=N2)CCOC3=CC=C(C4=CC=C(OC(F)(F)F)C=C4)C=C13.[H]Cl

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: 2934.99.03.00

More Info:

Biological target: Eleclazine hydrochloride is a novel late Na+ current inhibitor with IC50 value of 0.7 uM.
In vitro activity: TBD
In vivo activity: Eleclazine (10 μM) inhibited INa in atrial and ventricular myocytes in a use-dependent manner consistent with preferential activated state block. Eleclazine produced voltage-dependent instantaneous inhibition in atrial and ventricular myocytes; it caused a negative shift in voltage of half-maximal inactivation and slowed the recovery of INa from inactivation in both cell types. Reference: Heart Rhythm O2. 2020 Aug;1(3):206-214. https://pubmed.ncbi.nlm.nih.gov/32864638/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 221.32

Preparing Stock Solutions

The following data is based on the product molecular weight 451.83 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
Formulation protocol: 1. 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. 2. 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.
In vitro protocol: TBD
In vivo protocol: 1. 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. 2. 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.

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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.