Dimethyl fumarate

Not to be confused with Dimethylformamide.

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.009.863 Edit this at Wikidata
EC Number
  • 210-849-0
KEGG
UNII
  • InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ checkY
    Key: LDCRTTXIJACKKU-ONEGZZNKSA-N checkY
  • InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
    Key: LDCRTTXIJACKKU-ONEGZZNKBJ
  • O=C(OC)\C=C\C(=O)OC
Properties
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)[1]
Boiling point 193 °C (379 °F; 466 K)[1]
Pharmacology
L04AX07 (WHO)
License data
By mouth
Legal status
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H312, H315, H317, H319, H335
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).
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Dimethyl fumarate (DMF) is the methyl ester of fumaric acid and is named after the earth smoke plant (Fumaria officinalis).[8] Dimethyl fumarate combined with three other fumaric acid esters (FAEs) is solely licensed in Germany as an oral therapy for psoriasis (brand name Fumaderm).[9] 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).[4] 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.[6][10] Dimethyl fumarate is thought to have immunomodulatory properties without causing significant immunosuppression.[11]

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.[12] Dimethyl fumarate is available as a generic medication.[13][7]

  1. ^ a b "Background document to the opinions on the Annex XV dossier proposing restrictions on Dimethylfumarate (DMFu)" (PDF). European Chemicals Agency. 16 March 2011. p. 9. Archived from the original (PDF) on 22 February 2021. Retrieved 19 July 2018.
  2. ^ Cite error: The named reference PS-UKlabel was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference MS-UKlabel was invoked but never defined (see the help page).
  4. ^ a b "Tecfidera- dimethyl fumarate kit Tecfidera- dimethyl fumarate capsule". DailyMed. Retrieved 13 February 2021.
  5. ^ "Tecfidera EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 25 May 2022.
  6. ^ a b "Skilarence EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 25 May 2022.
  7. ^ a b "Dimethyl fumarate Accord EPAR". European Medicines Agency. 12 October 2022. Retrieved 22 February 2023.
  8. ^ Linker RA, Haghikia A. Dimethyl fumarate in multiple sclerosis: latest developments, evidence and place in therapy. Ther Adv Chronic Dis. 2016;7(4):198-207.
  9. ^ Mrowietz, Ulrich; Altmeyer, Peter; Bieber, Thomas; et al. (2007). "Treatment of psoriasis with fumaric acid esters (Fumaderm)". Journal der Deutschen Dermatologischen Gesellschaft. 5 (8): 716–7. doi:10.1111/j.1610-0387.2007.06346.x. PMID 17659047. S2CID 7431706.
  10. ^ "Agency EM. Skilarence [Updated]". 17 September 2018. Archived from the original on 20 June 2018. Retrieved 26 February 2019.
  11. ^ McEntee, Joanne. "Fumaderm: what is the evidence for its efficacy and safety". North West Medicines Information Centre. Archived from the original on 5 May 2013. Retrieved 29 November 2012.
  12. ^ "Consumers: EU to ban dimethylfumarate (DMF) in consumer products, such as sofas and shoes" (Press release). European Commission. Retrieved 29 November 2012.
  13. ^ "Office of Generic Drugs 2020 Annual Report". U.S. Food and Drug Administration (FDA). Retrieved 12 February 2021.