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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 of ETHYL FUMARATE

SMILES

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

InChI

InChIKey=XLYMOEINVGRTEX-ONEGZZNKSA-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
Molecular Formula C6H8O4
Molecular Weight 144.1253
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
FUMADERM

Approved Use

Fumaderm, which contains fumaric acid esters (FAE), is used to treat psoriasis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

CYP2C19
2057

CYP1A2
2153
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 inconclusive [IC50 35.5742 uM]
CYP19A1
430
 no
CYP1A2
2333
 no
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP3A4
2633
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

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

Patents

US3332841
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:38:50 GMT 2025
Edited
by admin
on Mon Mar 31 18:38:50 GMT 2025
Record UNII
Y3W849NG2N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL FUMARATE
WHO-DD  
Systematic Name English
NSC-524101
Preferred Name English
Ethyl fumarate [WHO-DD]
Common Name English
MONO-ETHYL FUMARATE
Systematic Name English
MONOETHYL FUMARATE
Systematic Name English
FUMARIC ACID MONOETHYL ESTER
Systematic Name English
FUMARIC ACID, MONOETHYL ESTER
Common Name English
2-BUTENEDIOIC ACID (E)-, MONOETHYL ESTER
Common Name English
ETHYL HYDROGEN FUMARATE
Systematic Name English
Classification Tree Code System Code
WHO-ATC D05BX51
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
219-544-7
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
EVMPD
SUB13741MIG
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
EVMPD
SUB13744MIG
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
MESH
C061175
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
PUBCHEM
5358902
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID701021503
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
SMS_ID
100000078990
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
NSC
524101
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
FDA UNII
Y3W849NG2N
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
RXCUI
52882
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY RxNorm
CAS
2459-05-4
Created by admin on Mon Mar 31 18:38:50 GMT 2025 , Edited by admin on Mon Mar 31 18:38:50 GMT 2025
PRIMARY
Related Record Type Details
Structure of CALCIUM MONOETHYLFUMARATE
SALT/SOLVATE -> PARENT
NIH
NCATS
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