ELECLAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H16F3N3O3
Molecular Weight	415.3652
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)OC1=CC=C(C=C1)C2=CC3=C(OCCN(CC4=NC=CC=N4)C3=O)C=C2

InChI

InChIKey=YNUAEEJQYHYLMS-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H16F3N3O3
Molecular Weight	415.3652
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800037785 | https://www.ncbi.nlm.nih.gov/pubmed/27690427

Eleclazine (formerly known as GS-6615) is a dihydrobenzoxazepinone selective cardiac late sodium current inhibitor. Gilead Sciences is developing eleclazine as an oral treatment for long QT syndrome, hypertrophic cardiomyopathy, ischaemic heart disease, and Ventricular arrhythmias.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29017927	Blocker 537		0.97 µM [IC50]

PubMed

Title	Date	PubMed
Structure-based design, synthesis, and biological evaluation of novel 1,4-diazepines as HDM2 antagonists.	2005 Apr 1	15780621
Discovery and cocrystal structure of benzodiazepinedione HDM2 antagonists that activate p53 in cells.	2005 Feb 24	15715460
Substituted 1,4-benzodiazepine-2,5-diones as alpha-helix mimetic antagonists of the HDM2-p53 protein-protein interaction.	2006 Mar	16611213
Design and modular parallel synthesis of a MCR derived alpha-helix mimetic protein-protein interaction inhibitor scaffold.	2006 Mar 15	16427279

Patents

Sample Use Guides

In Vivo Use Guide

Phase 3 clinical trial designed to determine the efficacy, safety, and tolerability of the late sodium current inhibitor eleclazine in shortening the corrected QT (QTcF) interval in subjects with type 3 Long QT Syndrome (LQT3). 41 subjects with genotype-confirmed LQT3 received a 48 mg oral loading dose of eleclazine followed by 12 weeks of treatment with 3 mg oral eleclazine once daily and then 12 weeks of treatment with 6 mg oral eleclazine once daily.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:03:02 GMT 2023` Edited by `admin` on `Sat Dec 16 05:03:02 GMT 2023`
Record UNII	PUY08529FK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELECLAZINE

Official Name

English

Eleclazine [WHO-DD]

Common Name

English

ELECLAZINE [USAN]

Common Name

English

eleclazine [INN]

Common Name

English

1,4-BENZOXAZEPIN-5(2H)-ONE, 3,4-DIHYDRO-4-(2-PYRIMIDINYLMETHYL)-7-(4-(TRIFLUOROMETHOXY)PHENYL)-

Systematic Name

English

GS-6615

Code

English

4-(PYRIMIDIN-2-YLMETHYL)-7-(4-(TRIFLUOROMETHOXY)PHENYL)-3,4-DIHYDRO-1,4-BENZOXAZEPIN-5(2H)-ONE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

446214