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Details

Stereochemistry ACHIRAL
Molecular Formula C5H6O4
Molecular Weight 130.0987
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MONOMETHYL FUMARATE

SMILES

COC(=O)\C=C\C(O)=O

InChI

InChIKey=NKHAVTQWNUWKEO-NSCUHMNNSA-N
InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+

HIDE SMILES / InChI

Description

Dimethyl fumarate (DMF) is the methyl ester of fumaric acid. DMF was initially recognized as a very effective hypoxic cell radiosensitizer. Later, DMF combined with three other fumaric acid esters (FAE) was licensed in Germany as oral therapy for psoriasis (trade name Fumaderm). Phase III clinical trials found that DMF (BG-12) successfully reduced relapse rate and increased time to progression of disability in multiple sclerosis (trade name Tecfidera). DMF is thought to have immunomodulatory properties without significant immunosuppression. The mechanism of action of dimethyl fumarate in multiple sclerosis is not well understood. It is thought to involve dimethyl fumarate degradation to its active metabolite monomethyl fumarate (MMF) then MMF up-regulates the Nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway that is activated in response to oxidative stress. Dimethyl fumarate is marketed under the brand name Tecfidera.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Identification of anti-inflammatory drugs according to their capacity to suppress type-1 and type-2 T cell profiles.
2004 Dec
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats.
2005 Aug 15
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.
2005 Feb
The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.
2008 Oct 31
Role of Nuclear Factor (Erythroid-Derived 2)-Like 2 Signaling for Effects of Fumaric Acid Esters on Dendritic Cells.
2017
Recent advances in understanding NRF2 as a druggable target: development of pro-electrophilic and non-covalent NRF2 activators to overcome systemic side effects of electrophilic drugs like dimethyl fumarate.
2017
Dual action by fumaric acid esters synergistically reduces adhesion to human endothelium.
2018 Dec
Dimethyl fumarate treatment alters NK cell function in multiple sclerosis.
2018 Feb
Multiple mechanisms of dimethyl fumarate in amyloid β-induced neurotoxicity in human neuronal cells.
2018 Feb
Patents

Sample Use Guides

In Vivo Use Guide
462 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
NK cells from healthy controls were treated with 10 and 100 uM of monomethyl fumarate for 12 hours then washed and co-cultured for 24 hours at 1:5 E:T ratio with or without autologous labeled T cells. Using CD107a expression to measure NK cell degranulation, is was noted an increase in the proportion of degranulated NK cells following treatment with different monomethyl fumarate concentrations. These changes occurred without dramatic effects on NK cell viability.
Name Type Language
MONOMETHYL FUMARATE
USAN   INN  
Official Name English
METHYL HYDROGEN FUMARATE
Systematic Name English
MONOMETHYL FUMARATE [USAN]
Common Name English
MMF
Common Name English
FUMARIC ACID MONOMETHYL ESTER [MI]
Common Name English
FUMARIC ACID MONOMETHYL ESTER
MI  
Systematic Name English
MONOMETHYL FUMARATE [INN]
Common Name English
Code System Code Type Description
PUBCHEM
5369209
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY
RXCUI
1546433
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
220-412-6
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY
CAS
2756-87-8
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY
INN
11163
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY
EVMPD
SUB184027
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY
MERCK INDEX
M5586
Created by admin on Mon Oct 21 20:20:19 UTC 2019 , Edited by admin on Mon Oct 21 20:20:19 UTC 2019
PRIMARY Merck Index