Dimethyl fumarate

Category	Human immunodeficiency Virus (HIV)
CAS	624-49-7
Description	Dimethyl fumarate is a Nrf2 activator used to treat adults with relapsing forms of multiple sclerosis.

Quotation Now

Product Information

Synonyms	Tecfidera; Dimethylfumarate; Methyl fumarate
IUPAC Name	dimethyl (E)-but-2-enedioate
Molecular Weight	144.12
Molecular Formula	C6H8O4
Canonical SMILES	COC(=O)C=CC(=O)OC
InChI	InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChIKey	LDCRTTXIJACKKU-ONEGZZNKSA-N
Boiling Point	193.0°C at 760 mmHg
Melting Point	102-106 °C
Flash Point	91.1±0.0 °C
Purity	99.88%
Density	1.1±0.1 g/cm3
Solubility	In Vitro: DMSO : 62.5 mg/mL(433.64 mM;Need ultrasonic) H2O : 8.33 mg/mL(57.80 mM;ultrasonic and warming and heat to 60°C) In Vivo: 1.Add each solvent one by one:50%PEG300 >> 50% saline Solubility: 7.5 mg/mL (52.04 mM); Suspended solution; Need ultrasonic 2.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline Solubility: ≥ 2.08 mg/mL (14.43 mM); Clear solution 3.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline) Solubility: ≥ 2.08 mg/mL (14.43 mM); Clear solution 4.Add each solvent one by one:10% DMSO >> 90%corn oil Solubility: ≥ 2.08 mg/mL (14.43 mM); Clear solution
Appearance	White to off-white (Solid)
Application	Dermatologic agents; immunosuppressive agents; radiation-sensitizing agents
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Animal Admin	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. 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 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.
Complexity	141
Exact Mass	144.04225873
Index Of Refraction	1.435
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. 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. Dimethyl fumarate inhibits TNF-alpha-induced nuclear entry of NF-kappaB in rat heart endothelial cells (RHEC). Dimethyl fumarate, an immune modulator and inducer of the antioxidant response, suppresses HIV replication and neurotoxin release. Dimethyl fumarate could decrease recruitment of activated monocytes to the CNS in response to inflammatory mediators.
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. 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.
PSA	52.60000
Target	Keap1-Nrf2; Reactive Oxygen Species; HIV; Autophagy; Endogenous Metabolite
Vapor Pressure	0.5±0.3 mmHg at 25°C
XLogP3-AA	0.7