Monomethyl fumarate

Monomethyl fumarate
Clinical data
Trade names	Bafiertam
License data	US DailyMed: Monomethyl_fumarate;
Routes of; administration	By mouth
ATC code	None;
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name (2E)-4-methoxy-4-oxobut-2-enoic acid;
CAS Number	2756-87-8;
PubChem CID	5369209;
DrugBank	DB14219;
ChemSpider	4520322;
UNII	45IUB1PX8R;
KEGG	D11492;
ChEBI	CHEBI:167450;
ChEMBL	ChEMBL589586;
ECHA InfoCard	100.018.557
Chemical and physical data
Formula	C5H6O4
Molar mass	130.099 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)C=CC(=O)O;
	InChI 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]

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:

Dimethyl fumarate (brand name Tecfidera),^[4]^[5]
Diroximel fumarate (brand name Vumerity),^[6] approved by the FDA in October 2019.^[7]^[8]^[9]^[10]

Society and culture

Names

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

References

^ a b c d "Bafiertam- monomethyl fumarate capsule". DailyMed. Retrieved 13 February 2022.
^ "Bafiertam: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 29 April 2020.
^ "Drug Approval Package: Bafiertam". U.S. Food and Drug Administration (FDA). 30 November 2020. Retrieved 13 February 2022.
^ "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.
^ "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.
^ 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
^ "Vumerity (Previously BIIB098 and ALKS 8700)". Multiple Sclerosis News Today. 1 November 2019. Retrieved 21 February 2020.
^ "Biogen and Alkermes Announce FDA Approval of Vumerity (diroximel fumarate) for Multiple Sclerosis". Biogen. Retrieved 21 February 2020.
^ "Vumerity- diroximel fumarate capsule". DailyMed. 30 March 2020. Retrieved 30 June 2020.
^ "Drug Approval Package: Vumerity". U.S. Food and Drug Administration (FDA). 21 April 2020. Retrieved 30 June 2020.
^ World Health Organization (2020). "International nonproprietary names for pharmaceutical substances (INN) : recommended INN: list 80" (PDF). WHO Drug Information. 34 (1): 74.

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[Bafiertam_FDA_label-1] "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.

[fumarate-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.