ETHYLBISIMINOMETHYLGUAIACOL MANGANESE CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H18N2O4.Cl.Mn
Molecular Weight	416.738
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure of ETHYLBISIMINOMETHYLGUAIACOL MANGANESE CHLORIDE

Structure Search

SMILES

[Cl-].[Mn+3].COC1=CC=CC(\C=N\CC\N=C\C2=C([O-])C(OC)=CC=C2)=C1[O-]

InChI

InChIKey=YUZJJFWCXJDFOQ-GAMUHHASSA-K

InChI=1S/C18H20N2O4.ClH.Mn/c1-23-15-7-3-5-13(17(15)21)11-19-9-10-20-12-14-6-4-8-16(24-2)18(14)22;;/h3-8,11-12,21-22H,9-10H2,1-2H3;1H;/q;;+3/p-3/b19-11+,20-12+;;

HIDE SMILES / InChI

Molecular Formula	C18H18N2O4
Molecular Weight	326.3465
Charge	-2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Molecular Formula	Mn
Molecular Weight	54.938
Charge	3
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8970624 | https://www.ncbi.nlm.nih.gov/pubmed/16787839 | https://www.ncbi.nlm.nih.gov/pubmed/28152009

ETHYLBISIMINOMETHYLGUAIACOL MANGANESE CHLORIDE (EUK-134) is a synthetic manganese-porphyrin complex. It is a superoxide dismutase and catalase mimetic. EUK-134 can protect ischemically injured rat kidneys from ischemia-reperfusion syndrome when administered just before reperfusion. EUK-134 can markedly protect primary rat cortical neurons from hydrogen peroxide mediated oxidative stress. Treatment with EUK-134 prevented the force decrease and the actin modifications in pulmonary hypertension diaphragm bundles. EUK-134 is identified as a novel approach to attenuate cardiac hypertrophy and lends scope for the development of EUK-134 as a therapeutic agent in the management of human cardiovascular disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
superoxide dismutase activity 1 Target ID: GO:0004784 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8970624	Modulator 828
catalase activity 1 Target ID: GO:0004096 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8970624	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Ischemia-reperfusion syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8970624	Preventing	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11447830 https://www.ncbi.nlm.nih.gov/pubmed/16787839 https://www.ncbi.nlm.nih.gov/pubmed/28487634	Primary	Basic research	Unknown Approved Use Unknown
Pulmonary hypertension-induced diaphragm weakness 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28152009	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946937	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mitochondrial catalase overexpressed transgenic mice are protected against lung fibrosis in part via preventing alveolar epithelial cell mitochondrial DNA damage.	2016 Dec	27840320
Direct effect of chronic hypoxia in suppressing large conductance Ca(2+)-activated K(+) channel activity in ovine uterine arteries via increasing oxidative stress.	2016 Jan 15	26613808
Mitoprotective antioxidant EUK-134 stimulates fatty acid oxidation and prevents hypertrophy in H9C2 cells.	2016 Sep	27514538
RyR2-Mediated Ca(2+) Release and Mitochondrial ROS Generation Partake in the Synaptic Dysfunction Caused by Amyloid β Peptide Oligomers.	2017	28487634
Superoxide dismutase/catalase mimetic EUK-134 prevents diaphragm muscle weakness in monocrotalin-induced pulmonary hypertension.	2017	28152009
Mesenchymal Stem Cell Therapy Protects Lungs from Radiation-Induced Endothelial Cell Loss by Restoring Superoxide Dismutase 1 Expression.	2017 Apr 10	27572073
Targeting hepatocellular carcinoma with piperine by radical-mediated mitochondrial pathway of apoptosis: An in vitro and in vivo study.	2017 Jul	28341137
Klotho, an antiaging molecule, attenuates oxidant-induced alveolar epithelial cell mtDNA damage and apoptosis.	2017 Jul 1	28428174

Patents

Sample Use Guides

In Vivo Use Guide

Rat: a single injection at 0.2 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

The possible role of EUK-134, a mitoprotective antioxidant, in the prevention of hypertrophy of H9C2 cells was examined. The cells were stimulated with phenylephrine (50 uM), and hypertrophy was assessed based on cell volume and expression of brain natriuretic peptide and calcineurin. Pretreatment with EUK-134 (10 uM) was effective in the prevention of hypertrophic changes in H9C2 cells, reduction of oxidative stress, and prevention of metabolic shift. EUK-134 treatment improved the oxidative status of mitochondria and reversed hypertrophy-induced reduction of mitochondrial membrane potential.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 20:10:54 UTC 2023` Edited by `admin` on `Sat Dec 16 20:10:54 UTC 2023`
Record UNII	SM5YJ88LTU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYLBISIMINOMETHYLGUAIACOL MANGANESE CHLORIDE

Official Name

English

MANGANESE, CHLORO((2,2'-(1,2-ETHANEDIYLBIS((NITRILO-.KAPPA.N)METHYLIDYNE))BIS(6-METHOXYPHENOLATO-.KAPPA.O))(2-))-, (SP-5-13)-

Common Name

English

MANGANESE, CHLORO((2,2'-(1,2-ETHANEDIYLBIS(NITRILOMETHYLIDYNE))BIS(6-METHOXYPHENOLATO))(2-)-N2,N2',O1,O1')-

Common Name

English

EUK-134

Brand Name

English

PHENOL, 2,2'-(1,2-ETHANEDIYLBIS(NITRILOMETHYLIDYNE))BIS(6-METHOXY-, MANGANESE COMPLEX

Common Name

English

ETHYLBISIMINOMETHYLGUAIACOL MANGANESE CHLORIDE [INCI]

Common Name

English

Code System Code Type Description

FDA UNII

SM5YJ88LTU