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-UPHRSURJSA-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 |
|---|---|---|---|
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 |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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PubMed
| Title | Date | PubMed |
|---|---|---|
| Curcumin prevents maleate-induced nephrotoxicity: relation to hemodynamic alterations, oxidative stress, mitochondrial oxygen consumption and activity of respiratory complex I. | 2014-11 |
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| Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling. | 2013-08 |
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| Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity. | 2013-06 |
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| Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | 2010-05 |
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| Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy. | 2010-03 |
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| Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions. | 2008-07-14 |
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| Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. | 2006-08-01 |
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| Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. | 2006-06 |
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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. | 2005-10 |
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| Determination of ergometrine maleate by fluorescence detection. | 2005-06-01 |
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| Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. | 2004-03-30 |
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| Molecular machinery for non-vesicular trafficking of ceramide. | 2003-12-18 |
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| Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. | 2003-08 |
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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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| An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. | 2002-11-27 |
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| Molecular mechanism for the regulation of human mitochondrial NAD(P)+-dependent malic enzyme by ATP and fumarate. | 2002-07 |
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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. | 2002-05-15 |
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| Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique. | 2001-06 |
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| Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. | 2000-07 |
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| Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. | 1999-10-16 |
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| In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. | 1999-08 |
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| Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. | 1998-11 |
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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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| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996-12 |
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| Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats. | 1996-03 |
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| [Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995-12 |
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| Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994-06 |
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| Disposition of [14C]velnacrine maleate in rats, dogs, and humans. | 1993-11-01 |
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| Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
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| Ocular surface alteration after long-term treatment with an antiglaucomatous drug. | 1992-07 |
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| Antifungal activity of fumaric acid in mice infected with Candida albicans. | 1991-11 |
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| Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. | 1991-01-02 |
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| Menstrual migraine and intermittent ergonovine therapy. | 1989-06 |
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| Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan. | 1988-09 |
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| Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis. | 1986-03 |
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| Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid. | 1985-06 |
|
| The influence of long-term treatment with timolol on human tear lysozyme albumin content. | 1982 |
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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| Record UNII |
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C718
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MALEIC ACID
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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)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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