Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H8O4 |
| Molecular Weight | 144.1253 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)\C=C\C(=O)OC
InChI
InChIKey=LDCRTTXIJACKKU-ONEGZZNKSA-N
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
| Molecular Formula | C6H8O4 |
| Molecular Weight | 144.1253 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618https://www.ncbi.nlm.nih.gov/pubmed/12522577 | https://www.ncbi.nlm.nih.gov/pubmed/27614618 | https://www.ncbi.nlm.nih.gov/pubmed/20664170 | https://multiplesclerosisnewstoday.com/alks-8700-multiple-sclerosis/http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735https://www.ncbi.nlm.nih.gov/pubmed/28340950http://onlinelibrary.wiley.com/doi/10.1002/047084289X.rd344/fullhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204063s014lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20647102 | https://www.ncbi.nlm.nih.gov/pubmed/19595601
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618https://www.ncbi.nlm.nih.gov/pubmed/12522577 | https://www.ncbi.nlm.nih.gov/pubmed/27614618 | https://www.ncbi.nlm.nih.gov/pubmed/20664170 | https://multiplesclerosisnewstoday.com/alks-8700-multiple-sclerosis/http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735https://www.ncbi.nlm.nih.gov/pubmed/28340950http://onlinelibrary.wiley.com/doi/10.1002/047084289X.rd344/fullhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204063s014lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20647102 | https://www.ncbi.nlm.nih.gov/pubmed/19595601
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.
Originator
Sources: http://adisinsight.springer.com/drugs/800038403http://pubs.rsc.org/en/content/articlehtml/1925/CT/CT9252701868http://www.ncbi.nlm.nih.gov/pubmed/15991882
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL6182 |
|||
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: WP2884 |
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Target ID: GO:0070269 |
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Target ID: Q16236 Gene ID: 4780.0 Gene Symbol: NFE2L2 Target Organism: Homo sapiens (Human) |
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Target ID: Glutathione S-transferase |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Diagnostic | Unknown Approved UseUnknown |
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| Secondary | TECFIDERA Approved UseIndicated for the treatment of patients with relapsing forms of multiple sclerosis Launch Date1.36434234E12 |
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| Palliative | Unknown Approved UseUnknown |
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| Primary | TECFIDERA Approved UseTECFIDERA, 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 Date1.36425597E12 |
|||
| Preventing | Unknown Approved UseUnknown |
|||
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds. | 1977 Apr |
|
| The influence of long-term treatment with timolol on human tear lysozyme albumin content. | 1982 |
|
| Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid. | 1985 Jun |
|
| Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis. | 1986 Mar |
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| Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan. | 1988 Sep |
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| Menstrual migraine and intermittent ergonovine therapy. | 1989 Jun |
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| Antifungal activity of fumaric acid in mice infected with Candida albicans. | 1991 Nov |
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| Ocular surface alteration after long-term treatment with an antiglaucomatous drug. | 1992 Jul |
|
| Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
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| Disposition of [14C]velnacrine maleate in rats, dogs, and humans. | 1993 Nov-Dec |
|
| Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994 Jun |
|
| [Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995 Dec |
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| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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| Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats. | 1996 Mar |
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| Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. | 1998 |
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| A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids. | 1998 |
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| In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. | 1999 Aug |
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| Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. | 1999 Jul-Aug |
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| Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. | 2000 Jul |
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| Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique. | 2001 Jun |
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| Molecular mechanism for the regulation of human mitochondrial NAD(P)+-dependent malic enzyme by ATP and fumarate. | 2002 Jul |
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| An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. | 2002 Jul-Aug |
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| 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 |
|
| Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. | 2003 Aug |
|
| 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 |
|
| Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats. | 2005 Aug 15 |
|
| 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 |
|
| Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. | 2006 Aug 1 |
|
| 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 |
|
| Molecular mechanisms of Nrf2-mediated antioxidant response. | 2009 Feb |
|
| 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 |
|
| Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling. | 2013 Aug |
|
| 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 |
|
| Curcumin prevents maleate-induced nephrotoxicity: relation to hemodynamic alterations, oxidative stress, mitochondrial oxygen consumption and activity of respiratory complex I. | 2014 Nov |
|
| Recent advances in understanding NRF2 as a druggable target: development of pro-electrophilic and non-covalent NRF2 activators to overcome systemic side effects of electrophilic drugs like dimethyl fumarate. | 2017 |
|
| Dual action by fumaric acid esters synergistically reduces adhesion to human endothelium. | 2018 Dec |
|
| Multiple mechanisms of dimethyl fumarate in amyloid β-induced neurotoxicity in human neuronal cells. | 2018 Feb |
|
| Monomethyl fumarate treatment impairs maturation of human myeloid dendritic cells and their ability to activate T cells. | 2019 Jan |
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
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| Record UNII |
FO2303MNI2
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Validated (UNII)
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29708
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WHO-ATC |
N07XX09
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NCI_THESAURUS |
C798
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EU-Orphan Drug |
EU/3/18/1990
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FDA ORPHAN DRUG |
406713
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WHO-ATC |
L04AX07
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FDA ORPHAN DRUG |
607917
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WHO-VATC |
QN07XX09
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EMA ASSESSMENT REPORTS |
TECFIDERA (AUTHORIZED: MULTIPLE SCLEROSIS)
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C63670
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7045
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25942
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1373478
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C056020
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QQ-86
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7725
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637568
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M11738
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76004
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DB08908
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DTXSID4060787
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210-849-0
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SUB13608MIG
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4757
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CHEMBL2107333
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DIMETHYL FUMARATE
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Dimethyl fumarate
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FO2303MNI2
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624-49-7
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FO2303MNI2
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EXCRETED UNCHANGED |
MAJOR
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose
IN-VIVO
URINE
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose; Amount combined with other cysteine conjugates
IN-VIVO
URINE
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose; Amount combined with "Fumaric Acid"
IN-VIVO
PLASMA
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METABOLITE INACTIVE -> PARENT |
Unit: percent of total dose excreted (into Expired Air; 39.7% to 58.6%)
IN-VIVO
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose; Amount combined with other N-acetylcysteine conjugates
IN-VIVO
URINE
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose; Amount combined with other N-acetylcysteine conjugates
IN-VIVO
URINE
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METABOLITE INACTIVE -> PARENT |
Unit: percent of total dose excreted; Combined amount with "citric acid"
IN-VIVO
PLASMA
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METABOLITE INACTIVE -> PARENT |
Unit: percent of dose; Amount combined with other cysteine conjugates
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ACTIVE MOIETY |
Dimethyl fumarate is highly reactive: when administered orally, it does not survive long enough to be absorbed into blood without being attacked by GSH (detoxifying agent). However, part of it is hydrolyzed by esterases to produce monomethylfumarate, which is more resistant
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