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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

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

Approved Use

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

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:59:07 UTC 2023
Edited
by admin
on Fri Dec 15 16:59:07 UTC 2023
Record UNII
Y3W849NG2N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL FUMARATE
WHO-DD  
Systematic 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
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 Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
219-544-7
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
EVMPD
SUB13741MIG
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
EVMPD
SUB13744MIG
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
MESH
C061175
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
PUBCHEM
5358902
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
SMS_ID
100000078990
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
NSC
524101
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
FDA UNII
Y3W849NG2N
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
RXCUI
52882
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID70102150
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
CAS
2459-05-4
Created by admin on Fri Dec 15 16:59:07 UTC 2023 , Edited by admin on Fri Dec 15 16:59:07 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT