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. It is taken by mouth.

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

It was approved for medical use in the United States in April 2020.

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),
• Diroximel fumarate (brand name Vumerity), approved by the FDA in October 2019.

Society and culture

Names

Monomethyl fumarate is the international nonproprietary name (INN).

External links

• "Monomethyl fumarate". Drug Information Portal. U.S. National Library of Medicine.