U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4
Molecular Weight 116.0722
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Fumaric acid

SMILES

OC(=O)\C=C\C(O)=O

InChI

InChIKey=VZCYOOQTPOCHFL-OWOJBTEDSA-N
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Dimethyl fumarate (DMF) is the methyl ester of fumaric acid. DMF was initially recognized as a very effective hypoxic cell radiosensitizer. Later, DMF combined with three other fumaric acid esters (FAE) was licensed in Germany as oral therapy for psoriasis (trade name Fumaderm). Phase III clinical trials found that DMF (BG-12) successfully reduced relapse rate and increased time to progression of disability in multiple sclerosis (trade name Tecfidera). DMF is thought to have immunomodulatory properties without significant immunosuppression. The mechanism of action of dimethyl fumarate in multiple sclerosis is not well understood. It is thought to involve dimethyl fumarate degradation to its active metabolite monomethyl fumarate (MMF) then MMF up-regulates the Nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway that is activated in response to oxidative stress. Dimethyl fumarate is marketed under the brand name Tecfidera.

CNS Activity

Curator's Comment: Dimethyl fumarate is probably too hydrophilic to cross the blood-CNS barrier. DMF stabilized the BBB by preventing disruption of interendothelial tight junctions and gap formation, and decreased matrix metalloproteinase activity in brain tissue.

Originator

Curator's Comment: In September 2003, Biogen (now Biogen Idec) licensed exclusive worldwide rights (excluding Germany) from Fumapharm to develop and market BG 12.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96KS0
Gene ID: 112398.0
Gene Symbol: EGLN2
Target Organism: Homo sapiens (Human)
120.0 µM [IC50]
Target ID: Q9H6Z9
Gene ID: 112399.0
Gene Symbol: EGLN3
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9GZT9
Gene ID: 54583.0
Gene Symbol: EGLN1
Target Organism: Homo sapiens (Human)
80.0 µM [IC50]
Target ID: Glutathione S-transferase
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Secondary
TECFIDERA

Approved Use

Indicated for the treatment of patients with relapsing forms of multiple sclerosis

Launch Date

1.36434234E12
Palliative
Unknown

Approved Use

Unknown
Primary
TECFIDERA

Approved Use

TECFIDERA, dimethyl fumarate undergoes rapid presystemic hydrolysis by esterases and is converted to its active metabolite, monomethyl fumarate (MMF). TECFIDERA is indicated for the treatment of patients with relapsing forms of multiple sclerosis.

Launch Date

1.36425597E12
Preventing
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.87 mg/L
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.21 mg × h/L
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
64%
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Doses

Doses

DosePopulationAdverse events​
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources: Page: 6.1
unhealthy, adult
n = 769
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: adult
Sex: unknown
Population Size: 769
Sources: Page: 6.1
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources:
unhealthy, mean 37 years
n = 105
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: mean 37 years
Sex: M+F
Population Size: 105
Sources:
Other AEs: Gastrointestinal disturbance...
Other AEs:
Gastrointestinal disturbance (53%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Gastrointestinal disturbance 53%
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources:
unhealthy, mean 37 years
n = 105
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: mean 37 years
Sex: M+F
Population Size: 105
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.
1977 Apr
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986 Mar
Antifungal activity of fumaric acid in mice infected with Candida albicans.
1991 Nov
Ocular surface alteration after long-term treatment with an antiglaucomatous drug.
1992 Jul
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.
1994 Jun
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces.
1998
Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC.
2000 Jul
Molecular mechanism for the regulation of human mitochondrial NAD(P)+-dependent malic enzyme by ATP and fumarate.
2002 Jul
The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy.
2002 May 15
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
Molecular machinery for non-vesicular trafficking of ceramide.
2003 Dec 18
Identification of anti-inflammatory drugs according to their capacity to suppress type-1 and type-2 T cell profiles.
2004 Dec
Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics.
2004 Mar 30
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.
2005 Feb
Determination of ergometrine maleate by fluorescence detection.
2005 May-Jun
Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.
2005 Oct
Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts.
2006 Jun
The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.
2008 Oct 31
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
2010 Mar
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
DMF inhibits PDGF-BB induced airway smooth muscle cell proliferation through induction of heme-oxygenase-1.
2010 Oct 20
Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.
2011 Jan 14
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
2013 Oct
Role of Nuclear Factor (Erythroid-Derived 2)-Like 2 Signaling for Effects of Fumaric Acid Esters on Dendritic Cells.
2017
Dual action by fumaric acid esters synergistically reduces adhesion to human endothelium.
2018 Dec
Dimethyl fumarate treatment alters NK cell function in multiple sclerosis.
2018 Feb
Multiple mechanisms of dimethyl fumarate in amyloid β-induced neurotoxicity in human neuronal cells.
2018 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In group of dogs experimental Fanconi syndrome (generalized proximal tubular dysfunction) was induced with maleic acid (25 mg/kg iv, pH 7.3). https://www.ncbi.nlm.nih.gov/pubmed/1858895
in cow: The aim of this study was to determine the influence of fumaric acid (FA) on ruminal fermentation and its effects on the acid-base balance of seven ruminally and duodenally fistulated multiparous German Holstein cows. The experiment was conducted in a change-over design with three periods in which the animals were randomly arranged in one of three treatments: Control (C; without FA), 300 or 600 g FA per day. The diets consisted of 7.4 kg DM grass silage, 4.2 kg concentrate mixture and 0, 300 or 600 g FA or wheat starch as isocaloric compensation per day and cow. FA supplementation decreased the rumen pH, acetic acid and butyric acid and increased propionic acid in rumen fluid. The results of the single-strand conformation polymorphism analysis (SSCP) did not show an influence of FA on the microbial population in the rumen
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Maleic acid-induced inhibition of sugar and amino acid transport in the rat renal tubule was studied.
It was evaluated the effects of fumaric acid (FA) on tyrosinase activity and structure via enzyme kinetics and computational simulations. FA was found to be a reversible inhibitor of tyrosinase and its induced mechanism was the parabolic non-competitive inhibition type with IC50=13.7±0.25mM and Kislope=12.64±0.75mM. Kinetic measurements and spectrofluorimetry studies showed that FA induced regional changes in the active site of tyrosinase. One possible binding site for FA was identified under the condition without L-DOPA. The computational docking simulations further revealed that FA can interact with HIS263 and HIS85 at the active site. Furthermore, four important hydrogen bonds were found to be involved with the docking of FA on tyrosinase. By inhibiting tyrosinase and its central role in pigment production, FA is a potential natural antipigmentation agent.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:16:03 UTC 2022
Edited
by admin
on Fri Dec 16 16:16:03 UTC 2022
Record UNII
88XHZ13131
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Fumaric acid
FCC   FHFI   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
TRANS-BUTENEDIOIC ACID
Systematic Name English
2(TRANS)-BUTENEDIOIC ACID
Systematic Name English
BOLETIC-ACID
Common Name English
INS NO.297
Code English
SODIUM AUROTHIOMALATE IMPURITY B [EP IMPURITY]
Common Name English
FEMA NO. 2488
Code English
MALIC ACID IMPURITY A [EP IMPURITY]
Common Name English
FUMARIC ACID [MI]
Common Name English
E-297
Code English
2-BUTENEDIOIC ACID, (E)-
Common Name English
Fumaric acid [WHO-DD]
Common Name English
FUMARIC ACID [USP IMPURITY]
Common Name English
ETHYLENEDICARBOXYLIC ACID
Systematic Name English
ALLOMALEIC-ACID
Common Name English
(E)-BUTENEDIOIC ACID
Systematic Name English
FUMARIC ACID [INCI]
Common Name English
FUMARIC ACID [HSDB]
Common Name English
FUMARICUM ACIDUM [HPUS]
Common Name English
FUMARIC ACID [MART.]
Common Name English
NSC-2752
Code English
TRANS-1,2-ETHYLENEDICARBOXYLIC ACID
Common Name English
FUMARICUM ACIDUM
HPUS  
Common Name English
FUMARIC ACID [VANDF]
Common Name English
FUMARIC ACID [USP-RS]
Common Name English
FUMARIC ACID [FHFI]
Common Name English
FUMARIC ACID [II]
Common Name English
INS-297
Code English
FUMARIC ACID [FCC]
Common Name English
Classification Tree Code System Code
LOINC 13743-0
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
LOINC 25101-7
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
DSLD 1281 (Number of products:28)
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
NCI_THESAURUS C345
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
LOINC 2303-6
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
EPA PESTICIDE CODE 51201
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
WHO-VATC QD05AX01
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
LOINC 26799-7
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
CODEX ALIMENTARIUS (GSFA) INS-297
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
JECFA EVALUATION FUMARIC ACID
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
WHO-ATC D05AX01
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
CFR 21 CFR 522.84
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
LOINC 75081-0
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
JECFA EVALUATION INS-297
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL503160
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
JECFA MONOGRAPH
INS-297
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
CAS
623158-97-4
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
SUPERSEDED
DAILYMED
88XHZ13131
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
DRUG CENTRAL
3229
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
MERCK INDEX
M5586
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY Merck Index
DRUG BANK
DB01677
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
RXCUI
25389
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
CAS
110-17-8
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
HSDB
710
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
EVMPD
SUB13935MIG
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
FDA UNII
88XHZ13131
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
RXCUI
70598
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
ALTERNATIVE
WIKIPEDIA
FUMARIC ACID
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
CHEBI
18012
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
NSC
2752
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
EPA CompTox
DTXSID3021518
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
ECHA (EC/EINECS)
203-743-0
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
NCI_THESAURUS
C63655
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
PUBCHEM
444972
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
MESH
C032005
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
CHEBI
29806
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
RS_ITEM_NUM
1286708
Created by admin on Fri Dec 16 16:16:03 UTC 2022 , Edited by admin on Fri Dec 16 16:16:03 UTC 2022
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE INACTIVE
Unit: percent of total dose excreted; Combined amount with "citric acid"
IN-VIVO
PLASMA
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EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY