Dimethyl fumarate

Dimethyl fumarate

Names
IUPAC name Dimethyl (E)-butenedioate
Other names trans-1,2-Ethylenedicarboxylic acid dimethyl ester (E)-2-Butenedioic acid dimethyl ester
Identifiers
CAS Number	624-49-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:76004 N
ChemSpider	553171 Y
DrugBank	DB08908 N
ECHA InfoCard	100.009.863
EC Number	210-849-0
IUPHAR/BPS	7045
UNII	FO2303MNI2 Y
InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ Y Key: LDCRTTXIJACKKU-ONEGZZNKSA-N Y InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ Key: LDCRTTXIJACKKU-ONEGZZNKBJ
SMILES O=C(OC)\C=C\C(=O)OC
Properties
Chemical formula	C6H8O4
Molar mass	144.127 g/mol
Appearance	White crystalline solid
Density	1.37 g/cm3, solid
Melting point	102 to 105 °C (216 to 221 °F; 375 to 378 K)
Boiling point	192 to 193 °C (378 to 379 °F; 465 to 466 K)
Pharmacology
ATC code	N07XX09 (WHO)
Hazards
EU classification (DSD)	Harmful (Xn)
R-phrases	R21 R38 R41 R43
S-phrases	S26 S36 S37 S39
Related compounds
Related diesters	Diethyl fumarate, dimethyl maleate, dimethyl malonate, dimethyl adipate
Related compounds	Fumaric acid Methyl acrylate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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). Other diseases, such as necrobiosis lipoidica, granuloma annulare, and sarcoidosis were also found to respond to treatment with DMF in case reports or small patient series. 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.

In a non-medical use, DMF was applied as a biocide in furniture or shoes to prevent growths of mold during storage or transport in a humid climate. However, due to incidences of allergic reactions after skin contact the European Union banned DMF in consumer products since 1998, and since January 2009 the import of products containing DMF was also banned.

Dimethyl fumarate was shown to have a significant effect on relapse rate and time to progression in phase III clinical trials of multiple sclerosis.

Dimethyl fumarate was recommended for approval in the European Union as a peroral treatment for MS by EMA on March 21, 2013.

One serious side effect that has been described is progressive multifocal leukoencephalopathy.