U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H8O4
Molecular Weight 144.1253
Optical Activity UNSPECIFIED
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

Description

Ethyl maleate is supposed to be a toxic agent. Its administration induced acute aflatoxicosis in goats. Ethyl maleate is also used as a cross-linking agent for the synthesis of polymers.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FUMADERM
PubMed

PubMed

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

Patents

Sample Use Guides

In Vivo Use Guide
Fumaderm tablets containing ethyl fumarate are given orally. The first 3 weeks, the initial tablet is given using the following schedule: 1 tablet on the first week; 2 tablets on the second week; 3 tablets in the third week. After that, full strength tablets are used: 1 tablet on the fourth week; 2 tablets on the fifth week; 3 tablets on the sixth week; 4 tablets on the 7th week; 5 tablets on the 8th weeks and 6 tablets on the week 9.
Route of Administration: Oral
In Vitro Use Guide
Primary human spinal cord astrocytes were treated for 6 hours with 1, 3, or 6 ug/mL ofa mixture of ethyl fumarate salts (Ca2+, Mg2+, Zn2+). The salts induced the expression of TXNRD1, SRXN1, HMOX1, NQO1 and OSGIN1 genes.
Name Type Language
ETHYL FUMARATE
WHO-DD  
Systematic 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
ETHYL FUMARATE [WHO-DD]
Common Name English
NSC-524101
Code 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 Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
Code System Code Type Description
ECHA (EC/EINECS)
219-544-7
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY
EVMPD
SUB13741MIG
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY
EVMPD
SUB13744MIG
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY
MESH
C061175
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY
PUBCHEM
5358902
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY SWITZERF
RXCUI
52882
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY RxNorm
CAS
2459-05-4
Created by admin on Tue Mar 06 17:02:05 UTC 2018 , Edited by admin on Tue Mar 06 17:02:05 UTC 2018
PRIMARY