Record Information |
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Version | 4.0 |
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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 | 2017-12-07 02:36:16 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 hydroxycinnamic acids and derivatives class of compounds. Those are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Entacapone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Entacapone is a non-carcinogenic (not listed by IARC) potentially toxic compound. 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". Entacapone, sold under the brand name Comtan among others, is a medication commonly used in combination with other medications for the treatment of Parkinson's disease. Entacapone together with levodopa and carbidopa allows levodopa to have a longer effect in the brain and reduces Parkinson’s disease signs and symptoms for a greater length of time than levodopa and carbidopa therapy alone (Wikipedia). Side effect include increase the occurrence of orthostatic hypotension, severe rhabdomyolysis, dyskinesia, hallucinations, hyperkinesia, hypokinesia, dizziness, fatigu,e gastrointestinal effects including abdominal pain constipation diarrhea nausea (DrugBank). Management of Entacapone overdose is symptomatic; there is no known antidote to Comtan. Hospitalization is advised, and general supportive care is indicated. There is no experience with hemodialysis or hemoperfusion, but these procedures are unlikely to be of benefit, because Entacapone is highly bound to plasma proteins. An immediate gastric lavage and repeated doses of charcoal over time may hasten the elimination of Entacapone by decreasing its absorption/reabsorption from the GI tract. The adequacy of the respiratory and circulatory systems should be carefully monitored and appropriate supportive measures employed (L1712) (T3DB). Entacapone is an inhibitor drug of catechol O-methyltransferase, which catalyzes the reaction between catechol and S-adenosyl-L-methionine to produce guaiacol and S-adenosyl-L-homocysteine.. |
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Structure | |
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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 | MeSH | Novartis brand OF entacapone | MeSH |
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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 | This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These 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 | Health effect: |
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Disposition | Source: Route of exposure: |
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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 | 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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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-003r-4190000000-da6b28638ec4920bd58a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0059-6004900000-14645ab585cbbed0ca38 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4i-0329000000-8d20a5650e9c1b1c8275 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0329000000-8d20a5650e9c1b1c8275 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0009000000-6e08b463d5af43617517 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udr-1069000000-5075a6f93c2b72c3483a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fkc-9240000000-27e088a40b83e29661e0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-29c32f9a04e379fce5fe | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2009000000-6d53b89d8a9ecd3b180e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dl-9100000000-5f330d3ad8cb0af17a9a | View in MoNA |
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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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