Dimethyl fumarate

Dimethyl fumarate
Names
	Preferred IUPAC name Dimethyl (2E)-but-2-enedioate
	Other names trans-1,2-Ethylenedicarboxylic acid dimethyl ester; (E)-2-Butenedioic acid dimethyl ester
Identifiers
CAS Number	624-49-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:76004 ;
ChEMBL	ChEMBL2107333;
ChemSpider	553171 ;
DrugBank	DB08908 ;
ECHA InfoCard	100.009.863
EC Number	210-849-0;
IUPHAR/BPS	7045;
KEGG	D03846;
PubChem CID	637568;
UNII	FO2303MNI2 ;
CompTox Dashboard (EPA)	DTXSID4060787 ;
	InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ Key: LDCRTTXIJACKKU-ONEGZZNKSA-N ; 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	144.126 g·mol−1
Appearance	White crystalline solid
Density	1.37 g/cm3
Melting point	103.5 °C (218.3 °F; 376.6 K)
Boiling point	193 °C (379 °F; 466 K)
Pharmacology
ATC code	L04AX07 (WHO)
License data	EU EMA: by INN;
Routes of; administration	By mouth
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H312, H315, H317, H319, H335
Precautionary statements	P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
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). verify (what is ?) Infobox references

Dimethyl fumarate (DMF) is the methyl ester of fumaric acid and is named after the earth smoke plant (Fumaria officinalis). 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.

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