Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:21:20 UTC |
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Update Date | 2022-03-07 02:51:22 UTC |
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HMDB ID | HMDB0012226 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Entacapone |
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Description | Entacapone, also known as comtan or comtess, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Entacapone is a drug which is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic parkinson's disease who experience the signs and symptoms of end-of-dose "wearing-off". Based on a literature review a significant number of articles have been published on Entacapone. |
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Structure | CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+ |
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Synonyms | Value | Source |
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(e)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide | ChEBI | Comtan | ChEBI | Comtess | ChEBI | Entacapona | ChEBI | Entacaponum | ChEBI | N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide | ChEBI | (e)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide | Generator | (e)-Α-cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide | Generator | 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide | HMDB | Orion brand OF entacapone | HMDB | Novartis brand OF entacapone | HMDB |
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Chemical Formula | C14H15N3O5 |
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Average Molecular Weight | 305.286 |
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Monoisotopic Molecular Weight | 305.101170605 |
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IUPAC Name | (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide |
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Traditional Name | entacapone |
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CAS Registry Number | 130929-57-6 |
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SMILES | CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N |
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InChI Identifier | InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+ |
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InChI Key | JRURYQJSLYLRLN-BJMVGYQFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Hydroxycinnamic acids and derivatives |
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Alternative Parents | |
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Substituents | - Hydroxycinnamic acid or derivatives
- Nitrophenol
- Nitrobenzene
- Nitroaromatic compound
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Tertiary carboxylic acid amide
- Carboxamide group
- C-nitro compound
- Organic nitro compound
- Allyl-type 1,3-dipolar organic compound
- Propargyl-type 1,3-dipolar organic compound
- Carboxylic acid derivative
- Carbonitrile
- Nitrile
- Organic oxoazanium
- Organic 1,3-dipolar compound
- Organic nitrogen compound
- Organic zwitterion
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organopnictogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Entacapone,1TMS,isomer #1 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1 | 2708.9 | Semi standard non polar | 33892256 | Entacapone,1TMS,isomer #2 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O)C([N+](=O)[O-])=C1 | 2731.5 | Semi standard non polar | 33892256 | Entacapone,2TMS,isomer #1 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1 | 2752.1 | Semi standard non polar | 33892256 | Entacapone,1TBDMS,isomer #1 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1 | 2947.4 | Semi standard non polar | 33892256 | Entacapone,1TBDMS,isomer #2 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C([N+](=O)[O-])=C1 | 2966.0 | Semi standard non polar | 33892256 | Entacapone,2TBDMS,isomer #1 | CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1 | 3157.2 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Entacapone GC-MS (Non-derivatized) - 70eV, Positive | splash10-003r-4190000000-da6b28638ec4920bd58a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Entacapone GC-MS (2 TMS) - 70eV, Positive | splash10-0059-6004900000-14645ab585cbbed0ca38 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Entacapone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Entacapone LC-ESI-qTof , Positive-QTOF | splash10-0a4i-0329000000-8d20a5650e9c1b1c8275 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Entacapone , positive-QTOF | splash10-0a4i-0329000000-8d20a5650e9c1b1c8275 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOF | splash10-0a4i-0009000000-6e08b463d5af43617517 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOF | splash10-0udr-1069000000-5075a6f93c2b72c3483a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOF | splash10-0fkc-9240000000-27e088a40b83e29661e0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOF | splash10-0udi-0009000000-29c32f9a04e379fce5fe | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOF | splash10-0udi-2009000000-6d53b89d8a9ecd3b180e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOF | splash10-00dl-9100000000-5f330d3ad8cb0af17a9a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOF | splash10-0a4i-0009000000-62e9f24f62db1840e2e0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOF | splash10-001i-1292000000-28b9a09056bdc465cd19 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOF | splash10-0a4i-1590000000-58fe447bc05aa8420188 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOF | splash10-0udi-0039000000-85f49c3b07fd9b1dd7bd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOF | splash10-0pb9-1693000000-bf7093c3dc0b31a75e5d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOF | splash10-0a4j-5910000000-658aee735015de149a67 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00494 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB028870 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4444537 |
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KEGG Compound ID | C07943 |
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BioCyc ID | CPD-7662 |
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BiGG ID | Not Available |
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Wikipedia Link | Entacapone |
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METLIN ID | Not Available |
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PubChem Compound | 5281081 |
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PDB ID | Not Available |
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ChEBI ID | 4798 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Valkovic P, Benetin J, Blazicek P, Valkovicova L, Gmitterova K, Kukumberg P: Reduced plasma homocysteine levels in levodopa/entacapone treated Parkinson patients. Parkinsonism Relat Disord. 2005 Jun;11(4):253-6. Epub 2005 Apr 20. [PubMed:15878587 ]
- Durif F, Devaux I, Pere JJ, Delumeau JC, Bourdeix I: Efficacy and tolerability of entacapone as adjunctive therapy to levodopa in patients with Parkinson's disease and end-of-dose deterioration in daily medical practice: an open, multicenter study. Eur Neurol. 2001;45(2):111-8. [PubMed:11244274 ]
- Factor SA, Molho ES, Feustel PJ, Brown DL, Evans SM: Long-term comparative experience with tolcapone and entacapone in advanced Parkinson's disease. Clin Neuropharmacol. 2001 Sep-Oct;24(5):295-9. [PubMed:11586115 ]
- Leppanen J, Savolainen J, Nevalainen T, Forsberg M, Huuskonen J, Taipale H, Gynther J, Mannisto PT, Jarvinen T: Synthesis and in-vitro/in-vivo evaluation of orally administered entacapone prodrugs. J Pharm Pharmacol. 2001 Nov;53(11):1489-98. [PubMed:11732751 ]
- Authors unspecified: Entacapone/levodopa/carbidopa combination tablet: Stalevo. Drugs R D. 2003;4(5):310-1. [PubMed:12952501 ]
- Authors unspecified: Levodopa + carbidopa + entacapone. Entacapone: a second look: new preparations. Parkinson's disease: a modest effect. Prescrire Int. 2005 Apr;14(76):51-4. [PubMed:15875340 ]
- Gottwald MD: Entacapone, a catechol-O-methyltransferase inhibitor for treating Parkinson's disease: review and current status. Expert Opin Investig Drugs. 1999 Apr;8(4):453-62. [PubMed:15992091 ]
- Kinnings SL, Liu N, Buchmeier N, Tonge PJ, Xie L, Bourne PE: Drug discovery using chemical systems biology: repositioning the safe medicine Comtan to treat multi-drug and extensively drug resistant tuberculosis. PLoS Comput Biol. 2009 Jul;5(7):e1000423. doi: 10.1371/journal.pcbi.1000423. Epub 2009 Jul 3. [PubMed:19578428 ]
- Hamaue N, Ogata A, Terado M, Tsuchida S, Yabe I, Sasaki H, Hirafuji M, Togashi H, Aoki T: Entacapone, a catechol-O-methyltransferase inhibitor, improves the motor activity and dopamine content of basal ganglia in a rat model of Parkinson's disease induced by Japanese encephalitis virus. Brain Res. 2010 Jan 14;1309:110-5. doi: 10.1016/j.brainres.2009.10.055. Epub 2009 Oct 29. [PubMed:19879254 ]
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