Identification

Summary

Dimethyl fumarate is a medication used to treat patients with the relapsing-remitting form of multiple sclerosis.

Brand Names
Tecfidera
Generic Name
Dimethyl fumarate
DrugBank Accession Number
DB08908
Background

Dimethyl fumarate is an agent indicated for the treatment of relapsing forms of multiple sclerosis.3,4 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.4 Dimethyl fumarate is marketed under the brand name Tecfidera, and it was the third oral disease-modifying agent for multiple sclerosis approved by the FDA, following fingolimod and teriflunomide.2 Prior to its FDA approval, dimethyl fumarate had been used in Germany for treatment of psoriasis.2

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 144.1253
Monoisotopic: 144.042258744
Chemical Formula
C6H8O4
Synonyms
  • (E)-But-2-enedioic acid dimethyl ester
  • 1,2-bis(methoxycarbonyl)-trans-ethylene
  • Dimethyl fumarate
  • Dimethyl trans-ethylenedicarboxylate
  • Dimethylfumarat
  • Fumaric acid, dimethyl ester
  • trans-1,2-Ethylenedicarboxylic acid dimethyl ester
  • trans-Butenedioic acid dimethyl ester
External IDs
  • AZL O 211089
  • AZL-O-211089
  • BG 00012
  • BG 12
  • BG-00012
  • BG-12
  • BG00012
  • FAG-201
  • FP-187
  • FP187

Pharmacology

Indication

Dimethyl fumarate is indicated for the treatment of relapsing forms of multiple sclerosis (MS), including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease, in adults.4

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

The physiological effects of dimethyl fumarate on the body are not well understood. It has anti-inflammatory and cytoprotective effects, likely involved in its actions in multiple sclerosis (MS) patients.3 Dimethyl fumarate does not cause clinically significant QT interval prolongation. However, cases of progressive multifocal leukoencephalopathy, serious opportunistic infections, lymphopenia and liver injury have been reported in MS patients treated with this drug. Dimethyl fumarate may also cause anaphylaxis and angioedema.4

Mechanism of action

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). Both dimethyl fumarate and MMF up-regulate the Nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway that is activated in response to oxidative stress. Dimethyl fumarate also suppresses pro-inflammatory genes through nuclear factor kappa B inhibition. Additionally, MMF acts as an agonist at the nicotinic acid receptor, but the relevance of this is unknown.2,4

It has been suggested that dimethyl fumarate exerts its immunomodulatory effects through changes in the composition and phenotype of immune cells. It reduces CNS infiltration and alters the composition of all lymphocyte subpopulations, especially for cytotoxic and effector T cells. This causes a shift from a mainly pro-inflammatory phenotype to an anti-inflammatory one.3

TargetActionsOrganism
AKelch-like ECH-associated protein 1
binder
Humans
UTranscription factor p65
inhibitor
binder
Humans
Absorption

Once ingested, dimethyl fumarate is rapidly hydrolyzed by esterases to form monomethyl fumarate (MMF). Therefore, there is a negligible amount of dimethyl fumarate in the body, and all pharmacokinetic information is quantified with MMF.4 The time to maximum concentration (tmax) of MMF ranges between 2 and 2.5 hours. In patients with multiple sclerosis given 240 mg of dimethyl fumarate two times a day with food, the Cmax and AUC were 1.87 mg/L and 8.21 mg⋅hr/L, respectively. High-fat, high-calorie meals decrease the Cmax of MMF by 40% and cause a tmax delay from 2 hours to 5.5 hours; however, these changes are not considered clinically significant.4

Volume of distribution

In healthy people, monomethyl fumarate (MMF) has a variable volume of distribution of 53 to 73 litres.5

Protein binding

Monomethyl fumarate (MMF), the active metabolite of dimethyl fumarate, has a plasma protein binding range of 27 to 45%, and the binding process is concentration-independent.5

Metabolism

Dimethyl fumarate is quickly hydrolyzed by esterases in the gastrointestinal tract, tissues, and blood to form monomethyl fumarate (MMF), its active metabolite. MMF then undergoes subsequent metabolism through the tricarboxylic acid (TCA) cycle. The main metabolites of dimethyl fumarate are MMF, glucose, citric, and fumaric acid. Cytochrome P450 (CYP) enzymes do not participate in the metabolism of dimethyl fumarate.5

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Route of elimination

The main route of elimination of dimethyl fumarate is by CO2 exhalation, which accounts for 60% of the dose. The other minor routes of elimination are through the kidney (16% of the dose) and feces (1% of the dose). Trace amounts of unchanged monomethyl fumarate (the active metabolite of dimethyl fumarate) are present in urine.5

Half-life

The dimethyl fumarate metabolite monomethyl fumarate (MMF) has a short half-life of about 1 hour. MMF does not accumulate after repeated doses of dimethyl fumarate.4

Clearance

Monomethyl fumarate (MMF), the active metabolite of dimethyl fumarate, has a rapid clearance. Its apparent clearance (Cl/F) appears to be dose-independent.5

Adverse Effects
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Toxicity

Cases of overdose with dimethyl fumarate have been reported, and symptoms were consistent with its adverse event profile. There are no known therapeutic interventions to enhance dimethyl fumarate elimination nor an antidote. The product label of dimethyl fumarate recommends initiating symptomatic supportive treatment as clinically indicated in case of overdose.4 In vivo carcinogenicity studies found that at doses ranging between 200 and 400 mg/kg/day, mice had a higher incidence of non-glandular stomach and kidney tumors. The highest dose not associated with tumors in mice (75 mg/kg/day) is equivalent to the recommended human dose (RHD) of 480 mg/day.4 Dimethyl fumarate did not show evidence of mutagenicity in the in vitro bacterial reverse mutation (Ames) assay. Dimethyl fumarate was clastogenic in the in vitro chromosomal aberration assay in human peripheral blood lymphocytes in the absence of metabolic activation, but not clastogenic in the in vivo micronucleus assay in the rat.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Dimethyl fumarate.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Dimethyl fumarate.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Dimethyl fumarate.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Dimethyl fumarate.
AlefaceptThe risk or severity of adverse effects can be increased when Alefacept is combined with Dimethyl fumarate.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Dimethyl fumarate.
Allogeneic processed thymus tissueThe therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Dimethyl fumarate.
AltretamineThe risk or severity of adverse effects can be increased when Altretamine is combined with Dimethyl fumarate.
AmsacrineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Dimethyl fumarate.
AnakinraThe risk or severity of adverse effects can be increased when Anakinra is combined with Dimethyl fumarate.
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Food Interactions
  • Take with or without food. The incidence of flushing may be reduced by the administration of dimethyl fumarate with food; however, the product label states that it may be taken with or without food.

Products

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Active Moieties
NameKindUNIICASInChI Key
Monomethyl fumarateunknown45IUB1PX8R2756-87-8NKHAVTQWNUWKEO-NSCUHMNNSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dimethyl FumarateCapsule240 mg/1OralTeva Pharmaceuticals USA, Inc.2020-09-282024-04-30US flag
Dimethyl FumarateCapsule120 mg/1OralTeva Pharmaceuticals USA, Inc.2020-09-282023-03-31US flag
Dimethyl Fumarate MylanCapsule, delayed release120 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release240 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release240 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release120 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release240 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release240 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release120 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Dimethyl Fumarate MylanCapsule, delayed release120 mgOralMylan Ireland Limited2022-05-31Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-dimethyl FumarateCapsule, delayed release240 mgOralAccord Healthcare Inc2021-10-06Not applicableCanada flag
Ach-dimethyl FumarateCapsule, delayed release120 mgOralAccord Healthcare Inc2021-10-06Not applicableCanada flag
Apo-dimethyl FumarateCapsule, delayed release120 mgOralApotex Corporation2021-10-04Not applicableCanada flag
Apo-dimethyl FumarateCapsule, delayed release240 mgOralApotex Corporation2021-10-04Not applicableCanada flag
Dimethyl FumarateCapsule, delayed release240 mg/1OralLupin Pharmaceuticals, Inc.2020-10-31Not applicableUS flag
Dimethyl fumarateCapsule, delayed release240 mg/1OralAscend Laboratories, LLC2020-09-26Not applicableUS flag
Dimethyl fumarateCapsule120 mg/1OralPHARMATHEN INTERNATIONAL S.A.2021-08-01Not applicableUS flag
Dimethyl FumarateCapsule240 mg/1OralGlenmark Pharmaceuticals Inc., USA2020-10-06Not applicableUS flag
Dimethyl FumarateCapsule, delayed release120 mg/1OralZydus Lifesciences Limited2020-09-28Not applicableUS flag
Dimethyl FumarateCapsule, delayed release120 mg/1OralZydus Pharmaceuticals (USA) Inc.2020-09-28Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule; KitOralPHARMATHEN INTERNATIONAL S.A.2021-08-01Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralAmneal Pharmaceuticals NY LLC2020-09-28Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule; KitOralTWi Pharmaceuticals, Inc.2020-12-01Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralZydus Pharmaceuticals (USA) Inc.2020-09-28Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralAscend Laboratories, LLC2020-09-26Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralAccord Healthcare Inc.2022-09-26Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralCipla USA Inc.2020-09-24Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralLupin Pharmaceuticals, Inc.2020-10-31Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralCamber Pharmaceuticals, Inc.2020-09-24Not applicableUS flag
Dimethyl FumarateDimethyl fumarate (120 mg/1) + Dimethyl fumarate (240 mg/1)Capsule, delayed release; KitOralMsn Laboratories Private Limited2021-05-20Not applicableUS flag

Categories

ATC Codes
L04AX07 — Dimethyl fumarate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Fatty acid esters
Alternative Parents
Dicarboxylic acids and derivatives / Methyl esters / Enoate esters / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Enoate ester / Fatty acid ester / Hydrocarbon derivative / Methyl ester
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
diester, methyl ester, enoate ester (CHEBI:76004)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
FO2303MNI2
CAS number
624-49-7
InChI Key
LDCRTTXIJACKKU-ONEGZZNKSA-N
InChI
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
IUPAC Name
1,4-dimethyl (2E)-but-2-enedioate
SMILES
[H]\C(=C(\[H])C(=O)OC)C(=O)OC

References

Synthesis Reference

Pullagurla, MR., et al. (2020). Process for the synthesis of dimethyl fumarate (U.S. Patent No. US 10,626,076 B2). U.S. Patent and Trademark Office. https://patentimages.storage.googleapis.com/37/67/f2/c406d1a9840dac/US10626076.pdf

General References
  1. Papadopoulou A, D'Souza M, Kappos L, Yaldizli O: Dimethyl fumarate for multiple sclerosis. Expert Opin Investig Drugs. 2010 Dec;19(12):1603-12. doi: 10.1517/13543784.2010.534778. Epub 2010 Nov 11. [Article]
  2. Venci JV, Gandhi MA: Dimethyl fumarate (Tecfidera): a new oral agent for multiple sclerosis. Ann Pharmacother. 2013 Dec;47(12):1697-702. doi: 10.1177/1060028013509232. Epub 2013 Oct 23. [Article]
  3. Blair HA: Dimethyl Fumarate: A Review in Relapsing-Remitting MS. Drugs. 2019 Dec;79(18):1965-1976. doi: 10.1007/s40265-019-01229-3. [Article]
  4. FDA Approved Drug Products: TECFIDERA (dimethyl fumarate) delayed-release capsules for oral use [Link]
  5. EMA Assessment Report: Tecfidera (dimethyl fumarate) capsules for oral use [Link]
  6. Santa Cruz Biotechnology: Dimethyl fumarate SDS [Link]
Human Metabolome Database
HMDB0031257
KEGG Drug
D03846
PubChem Compound
637568
PubChem Substance
347827812
ChemSpider
553171
BindingDB
50504654
RxNav
1373478
ChEBI
76004
ChEMBL
CHEMBL2107333
ZINC
ZINC000003843378
PharmGKB
PA166152838
PDBe Ligand
EOU
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dimethyl_fumarate
PDB Entries
6lrz

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceRelapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedOtherRelapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentMultiple Sclerosis3
4CompletedTreatmentMultiple Sclerosis, Relapsing Forms of Multiple Sclerosis1
4CompletedTreatmentMultiple Sclerosis / Relapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
4CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)2
4RecruitingTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4TerminatedHealth Services ResearchMultiple Sclerosis1
4TerminatedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, delayed releaseOral
Capsule, delayed releaseOral120 mg/1
Capsule, delayed releaseOral240 mg/1
Capsule, delayed release; kitOral
CapsuleOral120 mg
CapsuleOral240 mg
TabletOral120 MG
TabletOral30 MG
Tablet, delayed releaseOral120 mg
Tablet, delayed releaseOral30 mg
Tablet, extended releaseOral30 MG
Capsule, delayed releaseOral120 mg
Capsule, delayed releaseOral240 mg
CapsuleOral120 mg/1
CapsuleOral240 mg/1
Capsule; kitOral
CapsuleOral
SolutionOral120.0 mg
SolutionOral240.0 mg
Capsule, coatedOral120 mg
Capsule, coatedOral240 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7320999No2008-01-222020-05-18US flag
US7619001No2009-11-172018-04-01US flag
US7803840No2010-09-282018-04-01US flag
US8399514No2013-03-192028-02-07US flag
US8524773No2013-09-032018-04-01US flag
US6509376No2003-01-212019-10-29US flag
US8759393No2014-06-242019-10-29US flag
US10391160No2019-08-272035-03-13US flag
US10959972No2021-03-302035-11-16US flag
US10555993No2020-02-112035-03-13US flag
US10994003No2021-05-042035-03-13US flag
US11007166No2021-05-182035-11-16US flag
US11007167No2021-05-182035-11-16US flag
US11129806No2021-09-282035-11-16US flag
US11246850No2015-11-162035-11-16US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)102From Santa Cruz Biotechnology SDS
boiling point (°C)192From Santa Cruz Biotechnology SDS
water solubilityHighly soluble in waterFrom FDA label
Predicted Properties
PropertyValueSource
Water Solubility12.9 mg/mLALOGPS
logP0.45ALOGPS
logP0.72Chemaxon
logS-1ALOGPS
pKa (Strongest Basic)-6.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area52.6 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity34.15 m3·mol-1Chemaxon
Polarizability13.76 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9600000000-85c5795d39a711edce4a
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9500000000-ef1a2c817c752048ca3d
GC-MS Spectrum - EI-BGC-MSsplash10-014i-6900000000-b4104322040a20afbf87
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9500000000-38079515fe54a7a128d6
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9500000000-8e3b99fc3ddb06539d43
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9800000000-d3ec2acefa5532f1d130
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Binder
General Function
Transcription factor binding
Specific Function
Acts as a substrate adapter protein for the E3 ubiquitin ligase complex formed by CUL3 and RBX1 and targets NFE2L2/NRF2 for ubiquitination and degradation by the proteasome, thus resulting in the s...
Gene Name
KEAP1
Uniprot ID
Q14145
Uniprot Name
Kelch-like ECH-associated protein 1
Molecular Weight
69665.765 Da
References
  1. Oh CJ, Kim JY, Choi YK, Kim HJ, Jeong JY, Bae KH, Park KG, Lee IK: Dimethylfumarate attenuates renal fibrosis via NF-E2-related factor 2-mediated inhibition of transforming growth factor-beta/Smad signaling. PLoS One. 2012;7(10):e45870. doi: 10.1371/journal.pone.0045870. Epub 2012 Oct 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Binder
Curator comments
Target undergoes covalent modification involving the cysteine 38 residue. This prevents nuclear translocation of the protein.
General Function
Ubiquitin protein ligase binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
RELA
Uniprot ID
Q04206
Uniprot Name
Transcription factor p65
Molecular Weight
60218.53 Da
References
  1. Kastrati I, Siklos MI, Calderon-Gierszal EL, El-Shennawy L, Georgieva G, Thayer EN, Thatcher GR, Frasor J: Dimethyl Fumarate Inhibits the Nuclear Factor kappaB Pathway in Breast Cancer Cells by Covalent Modification of p65 Protein. J Biol Chem. 2016 Feb 12;291(7):3639-47. doi: 10.1074/jbc.M115.679704. Epub 2015 Dec 18. [Article]

Drug created at June 20, 2013 01:12 / Updated at December 08, 2022 17:54