Monomethyl fumarate

Last updated

Monomethyl fumarate
Monomethyl fumarate skeletal.svg
Clinical data
Trade names Bafiertam
License data
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Identifiers
  • (2E)-4-methoxy-4-oxobut-2-enoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.018.557 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C5H6O4
Molar mass 130.099 g·mol−1
3D model (JSmol)
  • COC(=O)C=CC(=O)O
  • InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
  • Key:NKHAVTQWNUWKEO-NSCUHMNNSA-N

Monomethyl fumarate, sold under the brand name Bafiertam is a medication for the treatment of relapsing forms of multiple sclerosis, to include clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease, in adults. [1] It is taken by mouth. [1]

Contents

The most common adverse reactions are flushing, abdominal pain, diarrhea, and nausea. [1]

It was approved for medical use in the United States in April 2020. [2] [3]

Pharmacology

Monomethyl fumarate alters the NFE2L2 (Nuclear factor erythroid 2-related factor 2) transcription factor.

NFE2L2 (or NRF2) is a basic leucine zipper (bZIP) protein that regulates the expression of antioxidant proteins that protect against oxidative damage triggered by injury and inflammation. Several drugs that stimulate the NFE2L2 pathway are being studied for treatment of diseases that are caused by oxidative stress.

Two precursors are also approved:

Society and culture

Names

Monomethyl fumarate is the international nonproprietary name (INN). [11]

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<span class="mw-page-title-main">Fumaric acid</span> Organic compound

Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the C
4
H
2
O2−
4
ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

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<span class="mw-page-title-main">Dimethyl fumarate</span> Chemical compound

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References

  1. 1 2 3 4 "Bafiertam- monomethyl fumarate capsule". DailyMed. Retrieved 13 February 2022.
  2. "Bafiertam: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 29 April 2020.
  3. "Drug Approval Package: Bafiertam". U.S. Food and Drug Administration (FDA). 30 November 2020. Retrieved 13 February 2022.
  4. "Biogen Idec's Tecfidera (Dimethyl Fumarate) Approved in US as a First-Line Oral Treatment for Multiple Sclerosis" (Press release). Biogen Idec. 27 March 2013. Archived from the original on 12 May 2013. Retrieved 4 June 2013.
  5. "Drug Approval Package: Tecfidera (dimethyl fumarate) Delayed-Release Capsules NDA #204063". U.S. Food and Drug Administration (FDA). 24 December 1999. Retrieved 30 June 2020.
  6. Matthew Dodson et al., Modulating NRF2 in Disease: Timing Is Everything, Annual Review of Pharmacology and Toxicology, Vol. 59, January 2019, Review in Advance first posted online on September 26, 2018, https://doi.org/10.1146/annurev-pharmtox-010818-021856
  7. "Vumerity (Previously BIIB098 and ALKS 8700)". Multiple Sclerosis News Today. 1 November 2019. Retrieved 21 February 2020.
  8. "Biogen and Alkermes Announce FDA Approval of Vumerity (diroximel fumarate) for Multiple Sclerosis". Biogen. Retrieved 21 February 2020.
  9. "Vumerity- diroximel fumarate capsule". DailyMed. 30 March 2020. Retrieved 30 June 2020.
  10. "Drug Approval Package: Vumerity". U.S. Food and Drug Administration (FDA). 21 April 2020. Retrieved 30 June 2020.
  11. World Health Organization (2020). "International nonproprietary names for pharmaceutical substances (INN) : recommended INN: list 80" (PDF). WHO Drug Information. 34 (1): 74.