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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

Maleic acid monosodium salt. Used in water soluble polymers preparation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96KS0
Gene ID: 112398.0
Gene Symbol: EGLN2
Target Organism: Homo sapiens (Human)
120.0 µM [IC50]
Target ID: Q9H6Z9
Gene ID: 112399.0
Gene Symbol: EGLN3
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9GZT9
Gene ID: 54583.0
Gene Symbol: EGLN1
Target Organism: Homo sapiens (Human)
80.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The influence of long-term treatment with timolol on human tear lysozyme albumin content.
1982
Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid.
1985 Jun
Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan.
1988 Sep
Menstrual migraine and intermittent ergonovine therapy.
1989 Jun
Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.
1991 Jan 2
Antifungal activity of fumaric acid in mice infected with Candida albicans.
1991 Nov
Ocular surface alteration after long-term treatment with an antiglaucomatous drug.
1992 Jul
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Disposition of [14C]velnacrine maleate in rats, dogs, and humans.
1993 Nov-Dec
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.
1994 Jun
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995 Dec
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats.
1996 Mar
Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces.
1998
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
Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients.
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
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
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers.
2003 Aug
Molecular machinery for non-vesicular trafficking of ceramide.
2003 Dec 18
Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics.
2004 Mar 30
Determination of ergometrine maleate by fluorescence detection.
2005 May-Jun
Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.
2005 Oct
Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles.
2006 Aug 1
Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts.
2006 Jun
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
2010 Mar
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling.
2013 Aug
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Curcumin prevents maleate-induced nephrotoxicity: relation to hemodynamic alterations, oxidative stress, mitochondrial oxygen consumption and activity of respiratory complex I.
2014 Nov
Patents

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
Single dose of 0 mg/kg (control group), 6 mg/kg (low-dose group), and 60 mg/kg (high-dose group) of MA (Maleic acid) with DDW (double deionized water) as the vehicle were administered to SD rats via oral gavage.
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.
Forty-five extracted human maxillary central incisors were sectioned longitudinally into a total of 90 segments, were embedded in auto polymerizing acrylic resin, and were grounded flat with silicon carbide abrasive papers. Based on the test solutions used, samples were divided randomly into three groups: (1) the EDTA group, 1 mL of 17% EDTA for 1 minute (n = 30), (2) the maleic acid group, 1 mL of 7% maleic acid for 1 minute (n = 30), and (3) the control group, 1 mL of 0.9% saline for 1 minute (n = 30). Every group was then divided into two subgroups of 15 specimens each. In group 1a, 2a, and 3a, specimens were used to determine the microhardness of the root canal dentine in the coronal, middle, and apical third using Vicker's hardness tester. In groups 1b, 2b, and 3b, specimens were used for the determination of surface roughness of the root canal dentine using a roughness tester (Surtronic, Leicester, England). Maleic acid reduced the microhardness of root dentin similar to EDTA but increased the surface roughness significantly more than EDTA.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:27 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:27 GMT 2025
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
FUMARICUM ACIDUM
HPUS  
Preferred 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 [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
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 Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
LOINC 25101-7
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
DSLD 1281 (Number of products:28)
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
NCI_THESAURUS C345
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
LOINC 2303-6
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
EPA PESTICIDE CODE 51201
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
WHO-VATC QD05AX01
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
LOINC 26799-7
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-297
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
JECFA EVALUATION FUMARIC ACID
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
WHO-ATC D05AX01
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
CFR 21 CFR 522.84
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
LOINC 75081-0
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
JECFA EVALUATION INS-297
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL503160
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
CAS
623158-97-4
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
SUPERSEDED
DAILYMED
88XHZ13131
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
DRUG CENTRAL
3229
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
MERCK INDEX
m5586
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB01677
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
RXCUI
25389
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
SMS_ID
100000078671
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
CAS
110-17-8
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
HSDB
710
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
EVMPD
SUB13935MIG
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
FDA UNII
88XHZ13131
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
RXCUI
70598
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
ALTERNATIVE
WIKIPEDIA
FUMARIC ACID
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
CHEBI
18012
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
NSC
2752
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID3021518
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-743-0
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
NCI_THESAURUS
C63655
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
JECFA MONOGRAPH
164
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
PUBCHEM
444972
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
MESH
C032005
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
CHEBI
29806
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
RS_ITEM_NUM
1286708
Created by admin on Mon Mar 31 17:47:27 GMT 2025 , Edited by admin on Mon Mar 31 17:47:27 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
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Related Record Type Details
PARENT -> METABOLITE INACTIVE
Unit: percent of total dose excreted; Combined amount with "citric acid"
IN-VIVO
PLASMA
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
USP
Related Record Type Details
ACTIVE MOIETY