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
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+
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28340950https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28340950https://www.ncbi.nlm.nih.gov/pubmed/15987702 | https://www.ncbi.nlm.nih.gov/pubmed/17182618http://www.google.ru/patents/US3887480 | https://www.google.com/patents/US4668735
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL6182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19595601 |
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Target ID: Q96KS0 Gene ID: 112398.0 Gene Symbol: EGLN2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
120.0 µM [IC50] | ||
Target ID: Q9H6Z9 Gene ID: 112399.0 Gene Symbol: EGLN3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
60.0 µM [IC50] | ||
Target ID: Q9GZT9 Gene ID: 54583.0 Gene Symbol: EGLN1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17182618 |
80.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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PubMed
Title | Date | PubMed |
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The influence of long-term treatment with timolol on human tear lysozyme albumin content. | 1982 |
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Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid. | 1985 Jun |
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Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan. | 1988 Sep |
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Menstrual migraine and intermittent ergonovine therapy. | 1989 Jun |
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Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. | 1991 Jan 2 |
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Antifungal activity of fumaric acid in mice infected with Candida albicans. | 1991 Nov |
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Ocular surface alteration after long-term treatment with an antiglaucomatous drug. | 1992 Jul |
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Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
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Disposition of [14C]velnacrine maleate in rats, dogs, and humans. | 1993 Nov-Dec |
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Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994 Jun |
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[Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995 Dec |
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Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats. | 1996 Mar |
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Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. | 1998 |
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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 |
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Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. | 1998 |
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Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. | 1998 Nov |
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In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. | 1999 Aug |
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Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. | 1999 Jul-Aug |
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Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. | 2000 Jul |
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An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. | 2002 Jul-Aug |
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The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy. | 2002 May 15 |
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Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. | 2003 |
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Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. | 2003 Aug |
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Molecular machinery for non-vesicular trafficking of ceramide. | 2003 Dec 18 |
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Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. | 2004 Mar 30 |
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Determination of ergometrine maleate by fluorescence detection. | 2005 May-Jun |
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Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. | 2005 Oct |
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Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. | 2006 Aug 1 |
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Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. | 2006 Jun |
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Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy. | 2010 Mar |
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Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | 2010 May |
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Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling. | 2013 Aug |
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Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity. | 2013 Jun |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28340950
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20647102
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
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on
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Record UNII |
88XHZ13131
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LOINC |
13743-0
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LOINC |
25101-7
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DSLD |
1281 (Number of products:28)
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NCI_THESAURUS |
C345
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LOINC |
2303-6
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EPA PESTICIDE CODE |
51201
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WHO-VATC |
QD05AX01
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LOINC |
26799-7
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CODEX ALIMENTARIUS (GSFA) |
INS-297
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JECFA EVALUATION |
FUMARIC ACID
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WHO-ATC |
D05AX01
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CFR |
21 CFR 522.84
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LOINC |
75081-0
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JECFA EVALUATION |
INS-297
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Code System | Code | Type | Description | ||
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CHEMBL503160
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623158-97-4
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88XHZ13131
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3229
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m5586
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PRIMARY | Merck Index | ||
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DB01677
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25389
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100000078671
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110-17-8
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710
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SUB13935MIG
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88XHZ13131
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70598
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FUMARIC ACID
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18012
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2752
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DTXSID3021518
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203-743-0
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C63655
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164
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444972
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C032005
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29806
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1286708
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE INACTIVE |
Unit: percent of total dose excreted; Combined amount with "citric acid"
IN-VIVO
PLASMA
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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