ETHYL MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8O4
Molecular Weight	144.1253
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)\C=C/C(O)=O

InChI

InChIKey=XLYMOEINVGRTEX-ARJAWSKDSA-N

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/517824 | https://www.google.com/patents/US3332841https://www.ncbi.nlm.nih.gov/pubmed/15479475

Ethyl fumarate is an anti-psoriatic agent. Its salts are used for the treatment of severe psoriasis (Fumaderm formulation). The mechanism of its action is unknown.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 87 Sources: https://www.sps.nhs.uk/wp-content/uploads/2015/10/NW-QA246.4-Fumaderm-for-psoriasis-.pdf	Primary		Approved 8583	FUMADERM Approved Use Fumaderm, which contains fumaric acid esters (FAE), is used to treat psoriasis.
Unknown 2596

C_max

Value	Dose	Co-administered	Analyte	Population
5.2 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20574745/	190 mg single, oral dose: 190 mg route of administration: Oral experiment type: SINGLE co-administered: MONOMETHYL FUMARATE	MONOMETHYL FUMARATE	ETHYL FUMARATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
63.6 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20574745/	190 mg single, oral dose: 190 mg route of administration: Oral experiment type: SINGLE co-administered: MONOMETHYL FUMARATE	MONOMETHYL FUMARATE	ETHYL FUMARATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
25.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20574745/	190 mg single, oral dose: 190 mg route of administration: Oral experiment type: SINGLE co-administered: MONOMETHYL FUMARATE	MONOMETHYL FUMARATE	ETHYL FUMARATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results	inconclusive [IC50 35.5742 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 18.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 49.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 48.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 49.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 48.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5358902#section=BioAssay-Results Page: 47.0

PubMed

Title	Date	PubMed
Dimethyl fumarate and monoethyl fumarate exhibit differential effects on KEAP1, NRF2 activation, and glutathione depletion in vitro.	2015	25793262
Use of fumaric acid esters in psoriasis.	2007-04-26	17456929
In vitro pharmacokinetics of anti-psoriatic fumaric acid esters.	2004-10-12	15479475
Treatment of psoriasis with fumaric acid esters: results of a prospective multicentre study. German Multicentre Study.	1998-03	9580799
Experimentally induced acute aflatoxicosis in goats treated with ethyl maleate, glutathione precursors, or thiosulfate.	1979-04	517824

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

NSC-11206

Preferred Name

English

ETHYL MALEATE

Systematic Name

English

MONOETHYL (2Z)-2-BUTENEDIOATE

Systematic Name

English

MALEIC ACID, ETHYL ESTER

Common Name

English

NSC-525207

Code

English

2-BUTENEDIOIC ACID (2Z)-, 1-ETHYL ESTER

Systematic Name

English

ETHYL HYDROGEN MALEATE

Systematic Name

English

MONOETHYL MALEATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

5354457