Dimethyl fumarate

Dimethyl fumarate
Clinical data
Other names	DHF; trans-1,2-Ethylenedicarboxylic acid dimethyl ester; (E)-2-Butenedioic acid dimethyl ester
License data	EU EMA: by INN;
Routes of; administration	Oral
Drug class	Immunomodulator
ATC code	L04AX07 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name Dimethyl (2E)-but-2-enedioate;
CAS Number	624-49-7 ;
PubChem CID	637568;
IUPHAR/BPS	7045;
DrugBank	DB08908 ;
ChemSpider	553171 ;
UNII	FO2303MNI2;
KEGG	D03846;
ChEBI	CHEBI:76004 ;
ChEMBL	ChEMBL2107333;
CompTox Dashboard (EPA)	DTXSID4060787 ;
ECHA InfoCard	100.009.863
Chemical and physical data
Formula	C6H8O4
Molar mass	144.126 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.37 g/cm3 g/cm3
Melting point	103.5 °C (218.3 °F)
Boiling point	193 °C (379 °F)
	SMILES O=C(OC)\C=C\C(=O)OC;
	InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ ; Key:LDCRTTXIJACKKU-ONEGZZNKSA-N ;
	(verify)

Dimethyl fumarate (DMF) is the methyl ester of fumaric acid. Dimethyl fumarate combined with three other fumaric acid esters (FAEs) is solely licensed in Germany as an oral therapy for psoriasis (brand name Fumaderm). Since 2013, it has been approved by the U.S. Food and Drug Administration (FDA) as a treatment option for adults with relapsing multiple sclerosis (brand name Tecfidera). In 2017, an oral formulation of dimethyl fumarate (brand name Skilarence) was approved for medical use in the European Union as a treatment for moderate-to-severe plaque psoriasis. Dimethyl fumarate is thought to have immunomodulatory properties without causing significant immunosuppression.

Dimethyl fumarate has also been applied as a biocide in furniture or shoes to prevent growths of mold during storage or transport in humid climates. However, due to cases of allergic reactions after skin contact, dimethyl fumarate-containing consumer products are no longer authorised to be manufactured (since 1998) or imported (since 2009) in the European Union. Dimethyl fumarate is available as a generic medication.