EOU

dimethyl (~{E})-but-2-enedioate

Created:2020-01-17
Last modified:  2020-08-05

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Chemical Details

Formal Charge0
Atom Count18
Chiral Atom Count0
Bond Count17
Aromatic Bond Count0
2D diagram of EOU

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Chemical Component Summary

Namedimethyl (~{E})-but-2-enedioate
Systematic Name (OpenEye OEToolkits)dimethyl (~{E})-but-2-enedioate
FormulaC6 H8 O4
Molecular Weight144.125
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESCACTVS3.385COC(=O)C=CC(=O)OC
SMILESOpenEye OEToolkits2.0.7COC(=O)C=CC(=O)OC
Canonical SMILESCACTVS3.385 COC(=O)/C=C/C(=O)OC
Canonical SMILESOpenEye OEToolkits2.0.7 COC(=O)/C=C/C(=O)OC
InChIInChI1.03 InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChIKeyInChI1.03 LDCRTTXIJACKKU-ONEGZZNKSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB08908 
NameDimethyl fumarate
Groups
  • investigational
  • approved
DescriptionDimethyl fumarate is an agent indicated for the treatment of relapsing forms of multiple sclerosis.[A253942,L43752] 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.[L43752] 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].[A253917] Prior to its FDA approval, dimethyl fumarate had been used in Germany for treatment of psoriasis.[A253917]
Synonyms
  • (E)-But-2-enedioic acid dimethyl ester
  • trans-1,2-Ethylenedicarboxylic acid dimethyl ester
  • Dimethyl fumarate
  • Dimethyl trans-ethylenedicarboxylate
  • 1,2-bis(methoxycarbonyl)-trans-ethylene
Brand Names
  • Jamp Dimethyl Fumarate
  • Dimethyl Fumarate Polpharma
  • Dimethyl Fumarate Neuraxpharm
  • Gln-dimethyl Fumarate
  • Dimethyl Fumarate
IndicationDimethyl 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.[L43752,L45668,L49831]
Categories
  • Acids, Acyclic
  • Anti-Inflammatory Agents
  • Antineoplastic and Immunomodulating Agents
  • Cytoprotective Agent
  • Dermatologicals
ATC-CodeL04AX07
CAS number624-49-7

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Kelch-like ECH-associated protein 1MQPDPRPSGAGACCRFLPLQSQCPEGAGDAVMYASTECKAEVTPSQHGNR...unknownbinder
Transcription factor p65MDELFPLIFPAEPAQASGPYVEIIEQPKQRGMRFRYKCEGRSAGSIPGER...unknowninhibitor,binder
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL2107333
PubChem 637568
ChEMBL CHEMBL2107333
ChEBI CHEBI:76004
COD 2203632