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Details

Stereochemistry ACHIRAL
Molecular Formula C11H13NO6
Molecular Weight 255.224
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIROXIMEL FUMARATE

SMILES

COC(=O)\C=C\C(=O)OCCN1C(=O)CCC1=O

InChI

InChIKey=YIMYDTCOUQIDMT-SNAWJCMRSA-N
InChI=1S/C11H13NO6/c1-17-10(15)4-5-11(16)18-7-6-12-8(13)2-3-9(12)14/h4-5H,2-3,6-7H2,1H3/b5-4+

HIDE SMILES / InChI

Molecular Formula C11H13NO6
Molecular Weight 255.224
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Dimethyl maleate is an organic compound, the (Z)-isomer of the dimethyl ester of fumaric acid. Dimethyl maleate can be synthesized from maleic anhydride and methanol, with sulfuric acid acting as acid catalyst, via a nucleophilic acyl substitution for the monomethyl ester, followed by a Fischer esterification reaction for the dimethyl ester. Dimethyl maleate is used in many organic syntheses as a dienophile for diene synthesis. It is used as an additive and intermediate for plastics, pigments, pharmaceuticals, and agricultural products. It is also an intermediate for the production of paints, adhesives, and copolymers.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
120.0 µM [IC50]
60.0 µM [IC50]
80.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Diagnostic
Unknown
Secondary
TECFIDERA
Palliative
Unknown
Primary
TECFIDERA
Preventing
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.87 mg/L
240 mg 2 times / day multiple, oral
MONOMETHYL FUMARATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
8.21 mg × h/L
240 mg 2 times / day multiple, oral
MONOMETHYL FUMARATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
240 mg 2 times / day multiple, oral
MONOMETHYL FUMARATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
64%
240 mg 2 times / day multiple, oral
MONOMETHYL FUMARATE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
462 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
NK cells from healthy controls were treated with 10 and 100 uM of monomethyl fumarate for 12 hours then washed and co-cultured for 24 hours at 1:5 E:T ratio with or without autologous labeled T cells. Using CD107a expression to measure NK cell degranulation, is was noted an increase in the proportion of degranulated NK cells following treatment with different monomethyl fumarate concentrations. These changes occurred without dramatic effects on NK cell viability.
Substance Class Chemical
Record UNII
K0N0Z40J3W
Record Status Validated (UNII)
Record Version