Monomethyl Fumarate

Summary

Monomethyl Fumarate (CHEMBL589586) is an approved small-molecule immunomodulator targeting HCAR2; indicated across 2 conditions including multiple sclerosis and relapsing-remitting multiple sclerosis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Targets: 1 (HCAR2)
• Indications: 2 conditions
• Clinical trials: 5
• Chemistry: 130.1 Da · C5H6O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL589586
Name	Monomethyl Fumarate
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5369209
ChEBI	CHEBI:167450
Molecular formula	C5H6O4
Molecular weight	130.1
InChIKey	NKHAVTQWNUWKEO-NSCUHMNNSA-N

SMILES: COC(=O)/C=C/C(=O)O

IUPAC name: (E)-4-methoxy-4-oxobut-2-enoic acid

ChEBI definition: A dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1.

Pharmacological roles (ChEBI): immunomodulator, antioxidant.

Other ChEBI roles (chemical / environmental): drug metabolite.

Also known as: Bafiertam, Fumarate de monomethyle, Fumarato de monometilo, Fumaric acid monomethyl ester, Monomethyl fumarate, NSC-523835, methyl fumarate, Monomethylfumarate, MONOMETHYL FUMARATE, monomethyl fumaric acid, METHYLHYDROGEN FUMARATE, Methyl fumarate

Patent coverage: 3,701 distinct patent families (11,528 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
HCAR2	HCA2 receptor	Full agonist	6.74	0.1%	Q8TDS4

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Hydroxycarboxylic acid receptor 2.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 2 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HCAR2	9.02	IC50	0.96	nM	CHEMBL_ACT_25729882
HCAR2	6.75	Ki	180	nM	CHEMBL_ACT_6178569

Target pathways

Aggregated over 1 target gene(s): HCAR2.

Top Reactome pathways

3 total, by targets touching each:

Pathway	Targets	Genes
Hydroxycarboxylic acid-binding receptors	1	HCAR2
Class A/1 (Rhodopsin-like receptors)	1	HCAR2
G alpha (i) signalling events	1	HCAR2

Dominant GO biological processes

GO term	Targets
neutrophil apoptotic process	1
G protein-coupled receptor signaling pathway	1
positive regulation of neutrophil apoptotic process	1
negative regulation of lipid catabolic process	1
positive regulation of adiponectin secretion	1
apoptotic process	1
signal transduction	1

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
multiple sclerosis	4	MONDO:0005301	MONDO:0005301
relapsing-remitting multiple sclerosis	1	MONDO:0005314	EFO:0003929

Clinical trials

Total trials: 5.

Phase distribution

Phase	Trials
PHASE1	3
Not specified	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04022473	PHASE1	COMPLETED	Study to Compare GI Tolerability Following Oral Administration of Bafiertam™ or Tecfidera to Healthy Volunteers
NCT04570670	PHASE1	COMPLETED	Comparative Bioavailability of BAFIERTAM™ (Monomethyl Fumarate) and Tecfidera® (Dimethyl Fumarate) in Healthy Subjects
NCT05181215	PHASE1	COMPLETED	Bioequivalence Study of Bafiertam 190 mg and Vumerity® 462 mg Delayed-Release Capsules in Fasting Healthy Subjects
NCT04925778	Not specified	WITHDRAWN	Observational Study in Patients With Relapsing-Remitting Multiple Sclerosis Switched to Bafiertam® From Dimethyl Fumarate
NCT05978531	Not specified	TERMINATED	Observational Study of Persistence on Bafiertam Treatment in Routine Clinical Practice

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

45 molecules share ≥1 primary target. Top 45 by shared-target count:

Molecule	Source	Status	Shared targets
ACIPIMOX	ChEMBL	Phase 4 (approved)	HCAR2
DIMETHYL	ChEMBL	Phase 4 (approved)	HCAR2
NIACIN	ChEMBL	Phase 4 (approved)	HCAR2
5-FLUORONICOTINIC ACID	ChEMBL	Phase 3	HCAR2
ACIFRAN	ChEMBL	Phase 2	HCAR2
SCH-900271	ChEMBL	Phase 2	HCAR2
Aclidinium Bromide	PubChem	Approved	HCAR2
Allopurinol	PubChem	Approved	HCAR2
Alprazolam	PubChem	Approved	HCAR2
Amitriptyline	PubChem	Approved	HCAR2
Beclomethasone	PubChem	Approved	HCAR2
Beclomethasone Dipropionate	PubChem	Approved	HCAR2
Belzutifan	PubChem	Approved	HCAR2
Carisoprodol	PubChem	Approved	HCAR2
Celecoxib	PubChem	Approved	HCAR2
cephalexin	PubChem	Approved	HCAR2
Cetirizine	PubChem	Approved	HCAR2
Cinnamic Acid	PubChem	Approved	HCAR2
Citalopram	PubChem	Approved	HCAR2
Clindamycin	PubChem	Approved	HCAR2
Clonazepam	PubChem	Approved	HCAR2
Clonidine	PubChem	Approved	HCAR2
Desloratadine	PubChem	Approved	HCAR2
Diazepam	PubChem	Approved	HCAR2
Diltiazem	PubChem	Approved	HCAR2
Famciclovir	PubChem	Approved	HCAR2
Fenofibrate	PubChem	Approved	HCAR2
Fluconazole	PubChem	Approved	HCAR2
Fluticasone Propionate	PubChem	Approved	HCAR2
Gemfibrozil	PubChem	Approved	HCAR2
Guaifenesin	PubChem	Approved	HCAR2
Hydroxyzine	PubChem	Approved	HCAR2
Isosorbide Mononitrate	PubChem	Approved	HCAR2
Lamotrigine	PubChem	Approved	HCAR2
Lorazepam	PubChem	Approved	HCAR2
Meclizine	PubChem	Approved	HCAR2
Metformin	PubChem	Approved	HCAR2
Metoclopramide	PubChem	Approved	HCAR2
Nifedipine	PubChem	Approved	HCAR2
Pantoprazole	PubChem	Approved	HCAR2
Pimozide	PubChem	Approved	HCAR2
Propoxyphene	PubChem	Approved	HCAR2
Valacyclovir	PubChem	Approved	HCAR2
Verapamil	PubChem	Approved	HCAR2
Zidovudine	PubChem	Approved	HCAR2