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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 20:58:11 UTC |
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HMDB ID | HMDB0000176 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Maleic acid |
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Description | Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. |
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Structure | |
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Synonyms | Value | Source |
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(Z)-2-Butenedioic acid | ChEBI | (Z)-Butenedioic acid | ChEBI | cis-1,2-Ethylenedicarboxylic acid | ChEBI | cis-But-2-enedioic acid | ChEBI | cis-Butenedioic acid | ChEBI | H2Male | ChEBI | Toxilic acid | ChEBI | Maleate | Kegg | (Z)-2-Butenedioate | Generator | (Z)-Butenedioate | Generator | cis-1,2-Ethylenedicarboxylate | Generator | cis-But-2-enedioate | Generator | cis-Butenedioate | Generator | Toxilate | Generator | (2Z)-2-Butenedioate | HMDB | (2Z)-2-Butenedioic acid | HMDB | (2Z)-But-2-enedioate | HMDB | (2Z)-But-2-enedioic acid | HMDB | (2Z)-Butene-2-dioate | HMDB | (2Z)-Butene-2-dioic acid | HMDB | 2-Butenedioate | HMDB | 2-Butenedioic acid | HMDB | cis-2-Butenedioate | HMDB | cis-2-Butenedioic acid | HMDB | Kyselina maleinova | HMDB | MAE | HMDB | Maleinic acid | HMDB | Malenic acid | HMDB | Malezid CM | HMDB | Scotchbond multipurpose etchant | HMDB | Maleic acid, disodium salt | MeSH | Maleic acid, monocopper (2+) salt | MeSH | Maleic acid, potassium salt | MeSH | Maleic acid, sodium salt | MeSH | Sodium maleate | MeSH | Hydrogen maleate | MeSH | Maleic acid, ammonium salt | MeSH | Maleic acid, calcium salt | MeSH | Maleic acid, iron salt | MeSH | Maleic acid, neodymium salt | MeSH | Maleic acid, dipotassium salt | MeSH | Maleic acid, monoammonium salt | MeSH | Maleic acid, monosodium salt | MeSH |
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Chemical Formula | C4H4O4 |
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Average Molecular Weight | 116.0722 |
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Monoisotopic Molecular Weight | 116.010958616 |
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IUPAC Name | (2Z)-but-2-enedioic acid |
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Traditional Name | maleic acid |
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CAS Registry Number | 110-16-7 |
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SMILES | OC(=O)\C=C/C(O)=O |
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InChI Identifier | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- |
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InChI Key | VZCYOOQTPOCHFL-UPHRSURJSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Environmental role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 130.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 441 mg/mL at 25 °C | Not Available | LogP | -0.48 | SANGSTER (1994) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0900000000-170a9d63d0cb31451c1d | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-001j-5940000000-59e85bafafc1675e24ad | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0uxs-9000000000-d768b92d45a58ec32ec7 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-617284552377852c7c46 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0910000000-15f30f525d5ea74dc9d4 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-170a9d63d0cb31451c1d | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001j-5940000000-59e85bafafc1675e24ad | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-4b46518e6c4f0c6724f2 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ba-9200000000-52f88e04bac0ff8cdf17 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00di-8920000000-06da44f348d0fe0358b3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-9200000000-77d8b2c7abcec2e3d5a1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9200000000-8d8a8b14a723e0363227 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0229-9700000000-061b31801a2ae4703fc5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0uxs-9000000000-d768b92d45a58ec32ec7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-2900000000-6bbe33cf398e663af0fc | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-9100000000-550ee9efb3babd781bca | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9000000000-18e922c569242e2111e7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-00di-9000000000-f344fe84d76f2bf06f91 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-00fu-9000000000-6f90988f5d68f87b52d2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00di-9400000000-99bc7f4db87479b4122a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-2900000000-6bbe33cf398e663af0fc | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9100000000-550ee9efb3babd781bca | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-18e922c569242e2111e7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-f344fe84d76f2bf06f91 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00fu-9000000000-6f90988f5d68f87b52d2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00di-9400000000-99bc7f4db87479b4122a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-9800000000-dbf34563376daeb2901f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00xs-9200000000-113bf08cdc77707ed3ad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00fr-9000000000-f32d7ec65e8649bc2b0a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-408d53a9fff7acc8ca23 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-6900000000-f149e9e5a34e27dd4d4e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fxt-9000000000-cae5f71dc27daaf17d9e | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | - Fibroblasts
- Neuron
- Pancreas
- Platelet
- Prostate
- Skeletal Muscle
- Spleen
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Urine | Detected and Quantified | 5.447 +/- 6.8 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 10.4 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 10.7 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.7 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.1 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.5 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.4 (0.3-0.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 10.7 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.1 umol/mmol creatinine | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 1.585 +/- 1.123 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Associated Disorders and Diseases |
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Disease References | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB04299 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB008113 |
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KNApSAcK ID | C00007417 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C01384 |
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BioCyc ID | MALEATE |
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BiGG ID | Not Available |
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Wikipedia Link | Maleic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 444266 |
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PDB ID | Not Available |
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ChEBI ID | 18300 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000084 |
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References |
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Synthesis Reference | Dethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Kotikoski H, Oksala O, Vapaatalo H, Aine E: Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. Acta Ophthalmol Scand. 2003 Aug;81(4):355-60. [PubMed:12859262 ]
- Herreras JM, Pastor JC, Calonge M, Asensio VM: Ocular surface alteration after long-term treatment with an antiglaucomatous drug. Ophthalmology. 1992 Jul;99(7):1082-8. [PubMed:1495787 ]
- Klose T, Welzel PB, Werner C: Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. Colloids Surf B Biointerfaces. 2006 Aug 1;51(1):1-9. Epub 2006 May 17. [PubMed:16797943 ]
- Renner L, Pompe T, Salchert K, Werner C: Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. Langmuir. 2004 Mar 30;20(7):2928-33. [PubMed:15835174 ]
- Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8. [PubMed:15924314 ]
- Goes MF, Sinhoreti MA, Consani S, Silva MA: Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. Braz Dent J. 1998;9(1):3-10. [PubMed:9835798 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7. [PubMed:2759844 ]
- Seki T, Wakabayashi M, Nakagawa T, Imamura M, Tamai T, Nishimura A, Yamashiki N, Okamura A, Inoue K: Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. Eur J Gastroenterol Hepatol. 1998 Nov;10(11):915-8. [PubMed:9872612 ]
- Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [PubMed:12895502 ]
- Lavit M, Saivin S, Boudra H, Michel F, Martin A, Cahiez G, Labaune JP, Chomard JM, Houin G: Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. Arzneimittelforschung. 2000 Jul;50(7):640-4. [PubMed:10965422 ]
- Strasser G, Grabner G: The influence of long-term treatment with timolol on human tear lysozyme albumin content. Graefes Arch Clin Exp Ophthalmol. 1982;218(2):93-5. [PubMed:7075967 ]
- Glazunova OO, Korepanova EA, Efimov VS, Smirnov AI, Vladimirov YuA: 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. Membr Cell Biol. 1998;12(3):401-9. [PubMed:10024972 ]
- Yoshida H, Onda M, Tajiri T, Uchida E, Arima Y, Mamada Y, Yamamoto K, Kaneko M, Terada Y, Kumazaki T: Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. Hepatogastroenterology. 1999 Jul-Aug;46(28):2612-5. [PubMed:10522050 ]
- Benderli Y, Gokce K, Buyukgokcesu S: In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. Quintessence Int. 1999 Aug;30(8):570-5. [PubMed:10635272 ]
- Liu Y, Yanai R, Lu Y, Hirano S, Sagara T, Nishida T: Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. J Glaucoma. 2006 Jun;15(3):255-9. [PubMed:16778650 ]
- Dorr J, Roth K, Zurbuchen U, Deisz R, Bechmann I, Lehmann TN, Meier S, Nitsch R, Zipp F: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. J Neuroimmunol. 2005 Oct;167(1-2):204-9. [PubMed:16043230 ]
- Turcan RG, Hillbeck D, Hartley TE, Gilbert PJ, Coe RA, Troke JA, Vose CW: Disposition of [14C]velnacrine maleate in rats, dogs, and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1037-47. [PubMed:7905382 ]
- Chen CN, Huang GF, Guo MK, Lin CP: An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. J Dent. 2002 Jul-Aug;30(5-6):189-94. [PubMed:12450709 ]
- Daykin CA, Foxall PJ, Connor SC, Lindon JC, Nicholson JK: The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy. Anal Biochem. 2002 May 15;304(2):220-30. [PubMed:12009699 ]
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