Dimethyl fumarate

Modify Date: 2024-01-02 21:38:28

Dimethyl fumarate Structure
Dimethyl fumarate structure
 Common Name Dimethyl fumarate
CAS Number 624-49-7 Molecular Weight 144.125
Density 1.1±0.1 g/cm3 Boiling Point 193.0±0.0 °C at 760 mmHg
Molecular Formula C6H8O4 Melting Point 102-106 °C(lit.)
MSDS Chinese USA Flash Point 91.1±0.0 °C
Symbol GHS07 GHS09
GHS07, GHS09		 Signal Word Warning

 Use of Dimethyl fumarate


Dimethyl fumarate is a nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator and induces upregulation of antioxidant gene expression.

 Names

Name dimethyl fumarate
Synonym More Synonyms

 Dimethyl fumarate Biological Activity

Description Dimethyl fumarate is a nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator and induces upregulation of antioxidant gene expression.
Related Catalog
In Vitro Dimethyl fumarate causes short-lived oxidative stress, which leads to increased levels and nuclear localization of the transcription factor nuclear factor erythroid 2-related factor 2 and a subsequent increase in glutathione synthesis and recycling in neuronal cells[1]. Dimethyl fumarate inhibits dendritic cell (DC) maturation by reducing inflammatory cytokine production (IL-12 and IL-6) and the expression of MHC class II, CD80, and CD86. Dimethyl fumarate impairs nuclear factor κB (NF-κB) signaling via reduced p65 nuclear translocalization and phosphorylation. Dimethyl fumarate inhibits maturation of DCs and subsequently Th1 and Th17 cell differentiation by suppression of both NF-κB and ERK1/2-MSK1 signaling[2]. Dimethyl fumarate inhibits TNF-alpha-induced nuclear entry of NF-kappaB in rat heart endothelial cells (RHEC)[3]. Dimethyl fumarate, an immune modulator and inducer of the antioxidant response, suppresses HIV replication and neurotoxin release. Dimethyl fumarate attenuates CCL2-induced monocyte chemotaxis, suggesting that Dimethyl fumarate could decrease recruitment of activated monocytes to the CNS in response to inflammatory mediators[4].
In Vivo Dimethyl fumarate inhibits nuclear entry of NF-kappaB in RHEC and reduces myocardial infarct size after ischemia and reperfusion in rats in vivo[3]. Dimethyl fumarate oral administration is shown to upregulate mRNA and protein levels of Nrf2 and Nrf2-regulated cytoprotective genes, attenuate 6-OHDA induced striatal oxidative stress and inflammation in C57BL/6 mice[5].
Animal Admin In a blinded design, the rats are assigned to one of the three experimental groups: a) to the DMF group receiving 10 mg/kg body weight DMF (dissolved in DMSO 2% in water), or b) to the vehicle group receiving only the vehicle (DMSO 2% in water; necessary to dissolve DMF), or c) to the positive control group receiving the vehicle plus ischemic preconditioning (IPC, known to reduce infarct size). This dose of 10 mg/kg body weight of DMF corresponded approximately to a maximally tolerated dose in man. As we could confirm in our in vitro experiments that DMF is the active compound, the in vivo experiments are performed with DMF but not with MHF. DMF and the vehicle, respectively, tail vein is administrated by i.v. 90 min before ischemia (under general anesthesia using isoflurane) as well as immediately before ischemia. Ischemic preconditioning is induced by two times 5 min episodes ischemia (induced by left coronary artery occlusion) each followed by 5 min of reperfusion (induced by releasing the snare). The experiments are performed (except pilot experiments) pair wise, i.e. two experiments in parallel avoiding identical group assignment. The present study are set up, and permitted to demonstrate a pharmacodynamic effect of DMF on myocardial infarct size in rats in vivo. An eventual mode of action should be investigated in vitro. The results from our in vitro experiments as well as results of other laboratories did not show any effect of MHF on NF-κB activation. Therefore, no experiment is included to exclude MHF from the mode of action of DMF.
References

[1]. Albrecht P, et al. Effects of dimethyl fumarate on neuroprotection and immunomodulation. J Neuroinflammation. 2012 Jul 7;9:163

[2]. Peng H, et al. Dimethyl fumarate inhibits dendritic cell maturation via nuclear factor κB (NF-κB) and extracellular signal-regulated kinase 1 and 2 (ERK1/2) and mitogen stress-activated kinase 1 (MSK1) signaling. J Biol Chem. 2012 Aug 10;287(33):28017-26.

[3]. Meili-Butz S, et al. Dimethyl fumarate, a small molecule drug for psoriasis, inhibits Nuclear Factor-kappaB and reduces myocardial infarct size in rats. Eur J Pharmacol. 2008 May 31;586(1-3):251-8.

[4]. Cross SA, et al. Dimethyl fumarate, an immune modulator and inducer of the antioxidant response, suppresses HIV replication and macrophage-mediated neurotoxicity: a novel candidate for HIV neuroprotection. J Immunol. 2011 Nov 15;187(10):5015-25.

[5]. Jing X, et al. Dimethyl fumarate attenuates 6-OHDA-induced neurotoxicity in SH-SY5Y cells and in animal model of Parkinson's disease by enhancing Nrf2 activity. Neuroscience. 2015 Feb 12;286:131-40

[6]. Li Y, et al. Dimethyl fumarate accelerates wound healing under diabetic condition. J Mol Endocrinol. 2018 Jul 23. pii: JME-18-0102.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 193.0±0.0 °C at 760 mmHg
Melting Point 102-106 °C(lit.)
Molecular Formula C6H8O4
Molecular Weight 144.125
Flash Point 91.1±0.0 °C
Exact Mass 144.042252
PSA 52.60000
LogP 0.62
Vapour Pressure 0.5±0.3 mmHg at 25°C
Index of Refraction 1.435
Storage condition Store at RT.
Stability Stable. Incompatible with acids, bases, oxidizing agents, reducing agents.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EM6125000
CHEMICAL NAME :
2-Butenedioic acid, dimethyl ester, (E)-
CAS REGISTRY NUMBER :
624-49-7
BEILSTEIN REFERENCE NO. :
0774590
LAST UPDATED :
199710
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C6-H8-O4
MOLECULAR WEIGHT :
144.14
WISWESSER LINE NOTATION :
1OV1U1VO1 -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,373,1986
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,373,1986 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIHAAP American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 30,470,1969
TYPE OF TEST :
LC - Lethal concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3100 mg/m3/10M
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NDRC** National Defense Research Committee, Office of Scientific Research and Development, Progress Report. Volume(issue)/page/year: NDCrc-132,Dec,1942
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIHAAP American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 30,470,1969

 Safety Information

Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning
Hazard Statements H312-H315-H317-H319-H411
Precautionary Statements P280-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R21;R36/37/38
Safety Phrases S26-S36/37/39
RIDADR UN 3077 9 / PGIII
WGK Germany 1
RTECS EM6125000
HS Code 2917140000

 Synthetic Route

 Customs

HS Code 2917190090
Summary 2917190090 acyclic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

 Articles25

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Novel Nrf2 activators from microbial transformation products inhibit blood-retinal barrier permeability in rabbits.

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Nuclear factor erythroid 2-related factor 2 (Nrf2) is a redox-sensitive transcription factor that binds to antioxidant response elements located in the promoter region of genes encoding many antioxida...
Quantitative determination of dimethyl fumarate in silica gel by solid-phase microextraction/gas chromatography/mass spectrometry and ultrasound-assisted extraction/gas chromatography/mass spectrometry.

Environ. Monit. Assess. 187 , 320, (2015)

Dimethyl fumarate (DMF) is a chemical compound which has been added to silica gel bags used for preserving leather products during shipment. DMF has recently been singled out due to its ability to ind...
Cold stress initiates the Nrf2/UGT1A1/L-FABP signaling pathway in chickens.

Poult. Sci. 94 , 2597-603, (2015)

Cold stress triggers an anti-oxidative response in animals regulated by Nrf2 (nuclear factor 2-like, NFE2L2) binding to deoxyribonucleic acid-regulatory sequences near stress-responsive genes. To iden...

 Synonyms

Dimethyl fumarate
EINECS 210-849-0
MFCD00064438
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