Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0723 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(\[H])(=C(/[H])\C(=O)O)/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+
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0723 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204063s014lbl.pdfhttp://onlinelibrary.wiley.com/doi/10.1002/047084289X.rd344/fullhttps://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/https://www.ncbi.nlm.nih.gov/pubmed/28340950https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735Curator'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: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204063s014lbl.pdfhttp://onlinelibrary.wiley.com/doi/10.1002/047084289X.rd344/fullhttps://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/https://www.ncbi.nlm.nih.gov/pubmed/28340950https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735
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
Maleic acid monosodium salt. Used in water soluble polymers preparation.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25725349https://www.ncbi.nlm.nih.gov/pubmed/28832396
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/15991882http://pubs.rsc.org/en/content/articlehtml/1925/CT/CT9252701868http://adisinsight.springer.com/drugs/800038403
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19595601 |
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Target ID: Q96KS0 Gene ID: 112398.0 Gene Symbol: EGLN2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
120.0 µM [IC50] | ||
Target ID: Q9H6Z9 Gene ID: 112399.0 Gene Symbol: EGLN3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
60.0 µM [IC50] | ||
Target ID: Q9GZT9 Gene ID: 54583.0 Gene Symbol: EGLN1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
80.0 µM [IC50] | ||
Target ID: WP2884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27614618 |
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Target ID: GO:0070269 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26096886 |
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Target ID: CHEMBL4420 |
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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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1287182 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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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 |
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Preventing | Unknown Approved UseUnknown |
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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 |
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Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid. | 1985 Jun |
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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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Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. | 1991 Jan 2 |
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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 |
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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 |
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Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994 Jun |
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[Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995 Dec |
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Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats. | 1996 Mar |
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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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Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. | 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 |
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Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. | 2003 Aug |
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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 |
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Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. | 2004 Mar 30 |
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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 |
|
Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions. | 2008 Jul 14 |
|
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 |
|
Role of Nuclear Factor (Erythroid-Derived 2)-Like 2 Signaling for Effects of Fumaric Acid Esters on Dendritic Cells. | 2017 |
|
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 |
|
Dimethyl fumarate treatment alters NK cell function in multiple sclerosis. | 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
The starting dose for TECFIDERA is 120 mg twice a day orally. After 7 days, the dose should be increased to the maintenance dose of 240 mg twice a day orally. Temporary dose reductions to 120 mg twice a day may be considered for individuals who do not tolerate the maintenance
dose. Within 4 weeks, the recommended dose of 240 mg twice a day should be resumed. Discontinuation of TECFIDERA should be considered for patients unable to tolerate return to the maintenance dose. The incidence of flushing may be reduced by administration of TECFIDERA with food. Alternatively, administration of non-enteric coated aspirin (up to a dose of 325 mg) 30 minutes prior to TECFIDERA dosing may reduce the incidence or severity of flushing.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21289642
Curator's Comment:: Maleic acid-induced inhibition of sugar and amino acid transport in the rat renal tubule was studied.
MMF did not affect endothelial cell growth when tested at 200 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 01:11:40 UTC 2021
by
admin
on
Sat Jun 26 01:11:40 UTC 2021
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Record UNII |
88XHZ13131
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LOINC |
13743-0
Created by
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LOINC |
25101-7
Created by
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DSLD |
1281 (Number of products:28)
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NCI_THESAURUS |
C345
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LOINC |
2303-6
Created by
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EPA PESTICIDE CODE |
51201
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WHO-VATC |
QD05AX01
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LOINC |
26799-7
Created by
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CODEX ALIMENTARIUS (GSFA) |
INS-297
Created by
admin on Sat Jun 26 01:11:41 UTC 2021 , Edited by admin on Sat Jun 26 01:11:41 UTC 2021
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JECFA EVALUATION |
FUMARIC ACID
Created by
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WHO-ATC |
D05AX01
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CFR |
21 CFR 522.84
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LOINC |
75081-0
Created by
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JECFA EVALUATION |
INS-297
Created by
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Code System | Code | Type | Description | ||
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CHEMBL503160
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PRIMARY | |||
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INS-297
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PRIMARY | |||
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1286708
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PRIMARY | USP-RS | ||
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623158-97-4
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SUPERSEDED | |||
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3229
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PRIMARY | |||
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M5586
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PRIMARY | Merck Index | ||
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DB01677
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25389
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PRIMARY | |||
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110-17-8
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PRIMARY | |||
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710
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PRIMARY | |||
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SUB13935MIG
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PRIMARY | |||
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88XHZ13131
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PRIMARY | |||
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70598
Created by
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ALTERNATIVE | |||
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FUMARIC ACID
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PRIMARY | |||
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110-17-8
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PRIMARY | |||
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203-743-0
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PRIMARY | |||
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C63655
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PRIMARY | |||
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444972
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PRIMARY | |||
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C032005
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PRIMARY |
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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
USP
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |