U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4
Molecular Weight 116.0722
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Fumaric acid

SMILES

OC(=O)\C=C\C(O)=O

InChI

InChIKey=VZCYOOQTPOCHFL-OWOJBTEDSA-N
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

HIDE SMILES / InChI
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20647102 | https://www.ncbi.nlm.nih.gov/pubmed/19595601

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

CNS Non-penetrant
1014
Curator's Comment: Dimethyl fumarate is probably too hydrophilic to cross the blood-CNS barrier. DMF stabilized the BBB by preventing disruption of interendothelial tight junctions and gap formation, and decreased matrix metalloproteinase activity in brain tissue.

Originator

Sugden, S.|Whittaker, H.
12
Curator's Comment: In September 2003, Biogen (now Biogen Idec) licensed exclusive worldwide rights (excluding Germany) from Fumapharm to develop and market BG 12.

Approval Year

1946
64
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Egl nine homolog 2
13
Target ID: Q96KS0
Gene ID: 112398.0
Gene Symbol: EGLN2
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 120.0 µM [IC50]
Egl nine homolog 3
19
Target ID: Q9H6Z9
Gene ID: 112399.0
Gene Symbol: EGLN3
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 60.0 µM [IC50]
Egl nine homolog 1
21
Target ID: Q9GZT9
Gene ID: 54583.0
Gene Symbol: EGLN1
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 80.0 µM [IC50]
Activator
1430
Inhibitor
8297
Activator
1430
Nuclear factor erythroid 2-related factor 2
20
Target ID: Q16236
Gene ID: 4780.0
Gene Symbol: NFE2L2
Target Organism: Homo sapiens (Human)
Activator
1430
Glutathione S-transferase
12
Target ID: Glutathione S-transferase
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Secondary
Approved
8429
TECFIDERA

Approved Use

Indicated for the treatment of patients with relapsing forms of multiple sclerosis

Launch Date

2013
Palliative
Preclinical
Unknown

Approved Use

Unknown
Primary
Approved
8429
TECFIDERA

Approved Use

TECFIDERA, dimethyl fumarate undergoes rapid presystemic hydrolysis by esterases and is converted to its active metabolite, monomethyl fumarate (MMF). TECFIDERA is indicated for the treatment of patients with relapsing forms of multiple sclerosis.

Launch Date

2013
Preventing
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.87 mg/L
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204063lbl.pdf
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.21 mg × h/L
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204063lbl.pdf
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204063lbl.pdf
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
64%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204063lbl.pdf
240 mg 2 times / day multiple, oral
dose: 240 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MONOMETHYL FUMARATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Doses

Doses

DosePopulationAdverse events​
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/210296s000lbl.pdf
Page: 6.1
unhealthy, adult
n = 769
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: adult
Sex: unknown
Population Size: 769
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/210296s000lbl.pdf
Page: 6.1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/210296s000lbl.pdf
Page: 6.1
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32629403/
unhealthy, mean 37 years
n = 105
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: mean 37 years
Sex: M+F
Population Size: 105
Sources:
https://pubmed.ncbi.nlm.nih.gov/32629403/
Other AEs: Gastrointestinal disturbance...
Other AEs:
Gastrointestinal disturbance (53%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/32629403/
AEs

AEs

AESignificanceDosePopulation
Gastrointestinal disturbance 53%
190 mg 2 times / day multiple, oral
Highest studied dose
Dose: 190 mg, 2 times / day
Route: oral
Route: multiple
Dose: 190 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32629403/
unhealthy, mean 37 years
n = 105
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: mean 37 years
Sex: M+F
Population Size: 105
Sources:
https://pubmed.ncbi.nlm.nih.gov/32629403/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111

P-gp
1461
CYP450
65
P-gp
257

CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 no
CYP
147
 no
P-gp
1650
 no
P-gp
1650
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
65
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
3B Scientific (Wuhan) Corp
3B4-0303
http://www.3bsc.com/index/pro_info.php?id=18151
3B Scientific (Wuhan) Corp
3B4-2852
http://www.3bsc.com/index/pro_info.php?id=77486
AK Scientific, Inc. (AKSCI)
O997
http://www.aksci.com/item_detail.php?cat=O997
Aaron Chemicals
AR002URG
http://www.aaronchem.com/2756-87-8
Achemtek
0104-021727
http://www.achemtek.com/2756-87-8
Alfa Chemistry
AP2756878
https://reagents.alfa-chemistry.com/product/mono-methyl-fumarate-cas-2756-87-8-9093.html
Alichem
490019201
http://www.alichem.com/en/products/2756-87-8.html
Ambeed
A983659
https://www.ambeed.com/products/2756-87-8.html
Ambinter
Amb10071357
http://www.ambinter.com/reference/10071357
ApexBio Technology
B7674
http://www.apexbt.com/mmf.html
Aurora Fine Chemicals LLC
A01.295.615
http://online.aurorafinechemicals.com/info?ID=A01.295.615
Aurum Pharmatech LLC
M-3444
http://www.Aurumpharmatech.com/Product/ProductDetails/M_3444
Avantor Inc
TCM2413-5G
https://us.vwr.com/store/product/16813484/fumaric-acid-monomethyl-ester-98-0-by-gc
BLD Pharm
BD00941719
http://www.bldpharm.com/products/2756-87-8.html
BLD Pharm
BD140326
http://www.bldpharm.com/products/2756-87-8.html
BioChemPartner
BCP18454
http://www.biochempartner.com/2756-87-8-BCP18454
BioSynth
J-017996
https://www.biosynth.com/en/products/all-products/products/J-017996.html
BioSynth
J-522708
https://www.biosynth.com/en/products/all-products/products/J-522708.html
CSNpharm
CSN22981
https://www.csnpharm.com/products/mmf.html
Chem Scene
CS-0026484
http://www.chemscene.com/2756-87-8.html
ChemMol
99067199
http://www.chemmol.com/chemmol/99067199.html
Chemspace
CSSB00011216927
https://chem-space.com/CSSB00011216927
DC Chemicals
DC33842
http://www.dcchemicals.com//product_show-Monomethyl_Fumarate.html
Hairui
MOJB01402
http://www.hairuichem.com/en/product/2756-87-8.html
LGC Standards
MM0352.03-0025
https://www.lgcstandards.com/US/en/p/MM0352.03-0025
Lab Network
LN01310370
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01310370
MedChem Express
HY-103252
https://www.medchemexpress.com/monomethyl-fumarate.html
MuseChem
R058046
https://www.musechem.com/product/R058046.html
OChem
4292
http://www.ocheminc.com/index.php?act=psearch&pid=56M878
Oakwood
102026
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=170495&ExtHyperLink=1
Oakwood
94823
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=79997&ExtHyperLink=1
Selleck Chemicals
S6889
http://www.selleckchem.com/products/monomethyl-fumarate.html
Sigma-Aldrich
651419_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/651419?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
92571_SIAL
https://www.sigmaaldrich.com/catalog/product/sial/92571?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S536016
http://www.smolecule.com/products/s536016
Smolecule
S759551
https://www.smolecule.com/products/s759551
TCI (Tokyo Chemical Industry)
M2413
http://www.tcichemicals.com/eshop/en/us/commodity/M2413/index.html
THE BioTek
bt-275065
https://www.thebiotek.com/product/inhibitors/bt-275065
Tocris
4511
https://www.tocris.com/products/mmf_4511
VladaChem
VL278632-1G
https://www.vladachem.com/product.php?products=2756-87-8
abcr GmbH
AB503712
http://www.abcr.com/shop/en/AB503712
abcr GmbH
AB558870
http://www.abcr.com/shop/en/AB558870
eNovation Chemicals
D382932
http://www.enovationchem.com/productDetails.asp?productID=D382932
eNovation Chemicals
D533508
https://www.enovationchem.com/ProductDetails.asp?ProductID=D533508
eNovation Chemicals
D695687
https://www.enovationchem.com/ProductDetails.asp?ProductID=D695687
iChemical
EBD2637923
http://www.ichemical.com/products/2756-87-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.
1977 Apr
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986 Mar
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids.
1998
Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma.
1998 Nov
In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions.
1999 Aug
Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer.
1999 Jul-Aug
Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC.
2000 Jul
Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique.
2001 Jun
An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition.
2002 Jul-Aug
The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy.
2002 May 15
Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers.
2003 Aug
Identification of anti-inflammatory drugs according to their capacity to suppress type-1 and type-2 T cell profiles.
2004 Dec
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats.
2005 Aug 15
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.
2005 Feb
Determination of ergometrine maleate by fluorescence detection.
2005 May-Jun
Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions.
2008 Jul 14
The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.
2008 Oct 31
Molecular mechanisms of Nrf2-mediated antioxidant response.
2009 Feb
DMF inhibits PDGF-BB induced airway smooth muscle cell proliferation through induction of heme-oxygenase-1.
2010 Oct 20
Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.
2011 Jan 14
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
2013 Oct
Bioanalysis of monomethyl fumarate in human plasma by a sensitive and rapid LC-MS/MS method and its pharmacokinetic application.
2017 Nov 30
Dimethyl fumarate treatment alters NK cell function in multiple sclerosis.
2018 Feb
Patents

Patents

03931155
12
03936310
12
03944560
33
03947593
15
03952104
19
03954754
14
03957757
16
03959288
12
03962257
13
03965126
12
03966938
13
03966957
13
03978121
80
03979408
12
03979443
12
03979513
12
03979515
16
03980643
12
03981917
80
03985750
12
03988454
12
03991102
12
03992445
14
04000306
13
04001271
12
04002766
13
04003932
12
04013660
13
04017653
12
04027027
15
04031127
13
04032639
12
04053606
14
04055654
19
04061759
13
04062829
14
04071524
20
04087421
12
04089860
12
04093538
12
04094870
16
04096263
14
04113565
12
04133881
12
04139623
12
04144235
12
04144342
15
04154941
20
04157444
12
04182869
12
04182872
12
04216218
12
04217352
13
04221776
14
04230710
12
04235976
12
04247705
12
04260619
14
04273782
14
04277470
12
04277498
16
04287290
13
04288447
12
04294841
13
04302590
14
04312876
14
04315023
12
04317830
16
04327098
12
04327107
12
04331676
17
04355034
13
04447360
14
04500457
12
04515717
20
04518533
13
04524028
13
04595394
16
04668735
12
04908313
12
04959496
12
05028614
12
05028723
12
05672719
12
05914385
13
06375974
12
06590120
12
06846835
14
07192969
12
07216966
12
20050065211
12
JP2000510837A
12
JP2003517028A
14
JP2004520474A
17
JP2007070531A
12
JP2007511658A
17
JP2008520815A
23
JP2009073854A
14
JP2010504257A
15
JP2011525213A
13
JP4021489B2
13
JP4290994B2
17
JPH01146803A
12
JPH02101089A
14
JPH03193978A
13
JPH0366680A
12
JPH05112739A
12
JPH05287006A
12
JPH06256639A
12
JPH06256640A
12
JPH06345823A
12
JPH08199178A
12
JPH0892503A
12
JPH09255523A
12
JPH10158217A
12
JPH1180068A
12
JPS5522610A
12
JPS5536230A
12
JPS56151782A
13
JPS56159202A
12
JPS5655401A
12
JPS5693708A
12
JPS57155250A
12
JPS57164176A
12
JPS58145763A
12
JPS58183761A
12
JPS5880386A
12
JPS61169286A
12
JPS61179790A
12
JPS61188476A
12
JPS61203185A
12
JPS612753A
12
JPS6160602A
12
JPS6220506A
14
JPS6222791A
14
JPS6222792A
12
JPS6372603A
12
JPS6383003A
12
US9302977
12
WO2014096425A2
12
WO2015140811A2
12
WO2017108960A1
12

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In group of dogs experimental Fanconi syndrome (generalized proximal tubular dysfunction) was induced with maleic acid (25 mg/kg iv, pH 7.3). https://www.ncbi.nlm.nih.gov/pubmed/1858895
462 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Maleic acid-induced inhibition of sugar and amino acid transport in the rat renal tubule was studied.
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
Created
by admin
on Fri Dec 15 15:07:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:44 GMT 2023
Record UNII
88XHZ13131
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Fumaric acid
FCC   FHFI   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
TRANS-BUTENEDIOIC ACID
Systematic Name English
2(TRANS)-BUTENEDIOIC ACID
Systematic Name English
BOLETIC-ACID
Common Name English
INS NO.297
Code English
SODIUM AUROTHIOMALATE IMPURITY B [EP IMPURITY]
Common Name English
FEMA NO. 2488
Code English
MALIC ACID IMPURITY A [EP IMPURITY]
Common Name English
FUMARIC ACID [MI]
Common Name English
E-297
Code English
2-BUTENEDIOIC ACID, (E)-
Common Name English
Fumaric acid [WHO-DD]
Common Name English
FUMARIC ACID [USP IMPURITY]
Common Name English
ETHYLENEDICARBOXYLIC ACID
Systematic Name English
ALLOMALEIC-ACID
Common Name English
(E)-BUTENEDIOIC ACID
Systematic Name English
FUMARIC ACID [INCI]
Common Name English
FUMARIC ACID [HSDB]
Common Name English
FUMARICUM ACIDUM [HPUS]
Common Name English
FUMARIC ACID [MART.]
Common Name English
NSC-2752
Code English
TRANS-1,2-ETHYLENEDICARBOXYLIC ACID
Common Name English
FUMARICUM ACIDUM
HPUS  
Common Name English
FUMARIC ACID [VANDF]
Common Name English
FUMARIC ACID [USP-RS]
Common Name English
FUMARIC ACID [FHFI]
Common Name English
FUMARIC ACID [II]
Common Name English
INS-297
Code English
FUMARIC ACID [FCC]
Common Name English
Classification Tree Code System Code
LOINC 13743-0
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
LOINC 25101-7
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
DSLD 1281 (Number of products:28)
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
NCI_THESAURUS C345
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
LOINC 2303-6
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
EPA PESTICIDE CODE 51201
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
WHO-VATC QD05AX01
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
LOINC 26799-7
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
CODEX ALIMENTARIUS (GSFA) INS-297
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
JECFA EVALUATION FUMARIC ACID
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
WHO-ATC D05AX01
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
CFR 21 CFR 522.84
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
LOINC 75081-0
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
JECFA EVALUATION INS-297
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL503160
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
CAS
623158-97-4
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
SUPERSEDED
DAILYMED
88XHZ13131
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
DRUG CENTRAL
3229
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
MERCK INDEX
m5586
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01677
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
RXCUI
25389
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
SMS_ID
100000078671
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
CAS
110-17-8
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
HSDB
710
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
EVMPD
SUB13935MIG
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
FDA UNII
88XHZ13131
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
RXCUI
70598
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
ALTERNATIVE
WIKIPEDIA
FUMARIC ACID
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
CHEBI
18012
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
NSC
2752
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID3021518
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-743-0
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
NCI_THESAURUS
C63655
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
JECFA MONOGRAPH
164
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
PUBCHEM
444972
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
MESH
C032005
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
CHEBI
29806
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1286708
Created by admin on Fri Dec 15 15:07:45 GMT 2023 , Edited by admin on Fri Dec 15 15:07:45 GMT 2023
PRIMARY
Related Record Type Details
Structure of QUETIAPINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of EMEDASTINE MONOFUMARATE
SALT/SOLVATE -> PARENT
Structure of TALSACLIDINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of AVITRIPTAN FUMARATE
SALT/SOLVATE -> PARENT
Structure of AFACIFENACIN SESQUIFUMARATE
SALT/SOLVATE -> PARENT
Structure of DERAMCICLANE FUMARATE
SALT/SOLVATE -> PARENT
Structure of METHAPYRILENE FUMARATE
SALT/SOLVATE -> PARENT
Structure of BEDAQUILINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of CLEMASTINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of SODIUM FUMARATE
SALT/SOLVATE -> PARENT
Structure of 1-(2-((4-CHLOROPHENYL)THIO)ETHYL)-6,7-DIMETHOXY-2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE FUMARATE, (±)-
SALT/SOLVATE -> PARENT
Structure of ZICRONAPINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of CEVIPABULIN FUMARATE
SALT/SOLVATE -> PARENT
Structure of ONVANSERTIB FUMARATE
SALT/SOLVATE -> PARENT
Structure of BERUPIPAM HEMIFUMARATE
SALT/SOLVATE -> PARENT
Structure of PHA-568487 FUMARATE
SALT/SOLVATE -> PARENT
Structure of ABT-925
SALT/SOLVATE -> PARENT
Structure of TEDISAMIL SESQUIFUMARATE
SALT/SOLVATE -> PARENT
Structure of BROVINCAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of CELIVARONE FUMARATE
SALT/SOLVATE -> PARENT
Structure of IPAZILIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of AMINOPROMAZINE MONOFUMARATE
SALT/SOLVATE -> PARENT
Structure of AZALOXAN FUMARATE
SALT/SOLVATE -> PARENT
Structure of TIAMULIN FUMARATE
SALT/SOLVATE -> PARENT
Structure of SEMOTIADIL FUMARATE
SALT/SOLVATE -> PARENT
Structure of ARTILIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM FUMARATE
SALT/SOLVATE -> PARENT
Structure of CLOVOXAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of AZD-8055 FUMARATE
SALT/SOLVATE -> PARENT
Structure of KETIPRAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of DISODIUM FUMARATE
SALT/SOLVATE -> PARENT
Structure of LIDOCAINE MALEATE
SALT/SOLVATE -> PARENT
Structure of NDD-094 FUMARATE
SALT/SOLVATE -> PARENT
Structure of COTININE FUMARATE
SALT/SOLVATE -> PARENT
Structure of Zinc fumarate
SALT/SOLVATE -> PARENT
Structure of LINOGLIRIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of DUOPERONE FUMARATE
SALT/SOLVATE -> PARENT
Structure of 2-CHLORO-10-OXO-11-(4-METHYL-1-PIPERAZINYL)-11H-DIBENZ(B,F)THIEPIN FUMARATE
SALT/SOLVATE -> PARENT
Structure of MEDIFOXAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of MIXIDINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of FESOTERODINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of KETOTIFEN FUMARATE
SALT/SOLVATE -> PARENT
Structure of BTS-67582
SALT/SOLVATE -> PARENT
Structure of 3-AMINOPROPIONITRILE FUMARATE
SALT/SOLVATE -> PARENT
Structure of COBIMETINIB FUMARATE
SALT/SOLVATE -> PARENT
Structure of APLINDORE FUMARATE
SALT/SOLVATE -> PARENT
Structure of BELAPERIDONE FUMARATE
SALT/SOLVATE -> PARENT
Structure of LEVORMELOXIFENE FUMARATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM FUMARATE
SALT/SOLVATE -> PARENT
Structure of EMEDASTINE DIFUMARATE
SALT/SOLVATE -> PARENT
Structure of ORG-2305
SALT/SOLVATE -> PARENT
Structure of MITEMCINAL FUMARATE
SALT/SOLVATE -> PARENT
Structure of BIS(3-AMINOPROPIONONITRILE) FUMARATE
SALT/SOLVATE -> PARENT
Structure of FERROUS FUMARATE
SALT/SOLVATE -> PARENT
Structure of MCN-2840-46
SALT/SOLVATE -> PARENT
Structure of Solifenacin fumarate
SALT/SOLVATE -> PARENT
Structure of SARACATINIB DIFUMARATE
SALT/SOLVATE -> PARENT
Structure of DOMAZOLINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of OXETORONE FUMARATE
SALT/SOLVATE -> PARENT
Structure of EPLIVANSERIN FUMARATE
SALT/SOLVATE -> PARENT
Structure of BENCYCLANE FUMARATE
SALT/SOLVATE -> PARENT
Structure of AZD-2327 SESQUIFUMARATE
SALT/SOLVATE -> PARENT
Structure of PICUMETEROL FUMARATE
SALT/SOLVATE -> PARENT
Structure of HOMOFENAZINE DIFUMARATE
SALT/SOLVATE -> PARENT
Structure of MEFENIDIL FUMARATE
SALT/SOLVATE -> PARENT
Structure of TRECETILIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of MAGNESIUM FUMARATE
SALT/SOLVATE -> PARENT
OAT-1
TRANSPORTER -> INHIBITOR
Structure of ALISKIREN HEMIFUMARATE
SALT/SOLVATE -> PARENT
Structure of TAMPRAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of LEVOSEMOTIADIL FUMARATE
SALT/SOLVATE -> PARENT
Structure of FEZOLAMINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of RUPATADINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of .ALPHA.-(1-METHYL-3-PYRROLIDYL)-.ALPHA.,.ALPHA.-DIPHENYL-N,N-DIMETHYLACETAMIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of PHENDIMETRAZINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of METHAFURYLENE FUMARATE
SALT/SOLVATE -> PARENT
Structure of AHR-5859 FUMARATE
SALT/SOLVATE -> PARENT
Structure of SSR-240612 FUMARATE
SALT/SOLVATE -> PARENT
Structure of FOROPAFANT FUMARATE
SALT/SOLVATE -> PARENT
Structure of DAZOPRIDE FUMARATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of DIMETHYL FUMARATE
PARENT -> METABOLITE INACTIVE
Unit: percent of total dose excreted; Combined amount with "citric acid"
IN-VIVO
PLASMA
Related Record Type Details
Structure of ALMOTRIPTAN MALATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Malic acid
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ALANINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
GOLD SODIUM THIOMALATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ASPARTIC ACID
PARENT -> IMPURITY
USP
Related Record Type Details
Structure of Fumaric acid
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