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Namespace Prefixes

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Statements

Subject Item
n2:DB00494
rdf:type
n7:Drug
n7:description
Entacapone is a selective, reversible catechol-O-methyl transferase (COMT) inhibitor for the treatment of Parkinson's disease. It is a member of the class of nitrocatechols. When administered concomittantly with levodopa and a decarboxylase inhibitor (e.g., carbidopa), increased and more sustained plasma levodopa concentrations are reached as compared to the administration of levodopa and a decarboxylase inhibitor.
n7:dosage
n12:271B5E4E-363D-11E5-9242-09173F13E4C5 n12:271B5E4F-363D-11E5-9242-09173F13E4C5
n7:generalReferences
# Najib J: Entacapone: a catechol-O-methyltransferase inhibitor for the adjunctive treatment of Parkinson's disease. Clin Ther. 2001 Jun;23(6):802-32; discussion 771. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11440283 # Chong BS, Mersfelder TL: Entacapone. Ann Pharmacother. 2000 Sep;34(9):1056-65. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10981253 # Poewe WH, Deuschl G, Gordin A, Kultalahti ER, Leinonen M: Efficacy and safety of entacapone in Parkinson's disease patients with suboptimal levodopa response: a 6-month randomized placebo-controlled double-blind study in Germany and Austria (Celomen study). Acta Neurol Scand. 2002 Apr;105(4):245-55. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11939936 # Brooks DJ, Sagar H: Entacapone is beneficial in both fluctuating and non-fluctuating patients with Parkinson's disease: a randomised, placebo controlled, double blind, six month study. J Neurol Neurosurg Psychiatry. 2003 Aug;74(8):1071-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12876237 # Forsberg M, Lehtonen M, Heikkinen M, Savolainen J, Jarvinen T, Mannisto PT: Pharmacokinetics and pharmacodynamics of entacapone and tolcapone after acute and repeated administration: a comparative study in the rat. J Pharmacol Exp Ther. 2003 Feb;304(2):498-506. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12538800 # Kaakkola S: Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson's disease. Drugs. 2000 Jun;59(6):1233-50. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10882160
n7:group
investigational approved
n7:halfLife
0.4-0.7 hour
n7:indication
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".
n7:manufacturer
n8:271B5E4C-363D-11E5-9242-09173F13E4C5
owl:sameAs
n4:DB00494 n31:DB00494
dcterms:title
Entacapone
adms:identifier
n16:Entacapone n17:PA164748726 n19:4798 n20:4444537 n21:5281081 n22:46508734 n23:0078-0327-05 n24:C07943 n25:D00781 n28:DB00494
n7:mechanismOfAction
The mechanism of action of entacapone is believed to be through its ability to inhibit COMT in peripheral tissues, altering the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to a greater reduction in the manifestations of parkinsonian syndrome.
n7:packager
n8:271B5E44-363D-11E5-9242-09173F13E4C5 n8:271B5E45-363D-11E5-9242-09173F13E4C5 n8:271B5E49-363D-11E5-9242-09173F13E4C5 n8:271B5E4A-363D-11E5-9242-09173F13E4C5 n8:271B5E46-363D-11E5-9242-09173F13E4C5 n8:271B5E47-363D-11E5-9242-09173F13E4C5 n8:271B5E48-363D-11E5-9242-09173F13E4C5 n8:271B5E4B-363D-11E5-9242-09173F13E4C5
n7:patent
n13:2342634 n13:5135950 n13:1334967 n13:6599530
n7:routeOfElimination
Entacapone is almost completely metabolized prior to excretion, with only a very small amount (0.2% of dose) found unchanged in urine. As only about 10% of the entacapone dose is excreted in urine as parent compound and conjugated glucuronide, biliary excretion appears to be the major route of excretion of this drug.
n7:synonym
N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide Comtess Comtan Entacapona (e)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide Entacaponum Entacapone
n7:toxicity
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
n7:volumeOfDistribution
* 20 L
n5:hasAHFSCode
n6:28-92-00
n7:foodInteraction
Take without regard to meals.
n7:mixture
n30:271B5E43-363D-11E5-9242-09173F13E4C5 n30:271B5E42-363D-11E5-9242-09173F13E4C5
n7:proteinBinding
98% (bind to serum albumin)
n7:synthesisReference
Pandurang Deshpande, Parven Luthra, Anand Pandey, Dharmesh Dhameliya, "Process for the preparation of (E)-2-cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-N, N-diethyl-2-propenamide (entacapone)." U.S. Patent US20060258877, issued November 16, 2006.
n26:hasConcept
n27:M0193491
foaf:page
n10:entac.htm n18:entacapone.html
n7:IUPAC-Name
n11:271B5E54-363D-11E5-9242-09173F13E4C5
n7:InChI
n11:271B5E5A-363D-11E5-9242-09173F13E4C5
n7:Molecular-Formula
n11:271B5E59-363D-11E5-9242-09173F13E4C5
n7:Molecular-Weight
n11:271B5E56-363D-11E5-9242-09173F13E4C5
n7:Monoisotopic-Weight
n11:271B5E57-363D-11E5-9242-09173F13E4C5
n7:SMILES
n11:271B5E58-363D-11E5-9242-09173F13E4C5
n7:Water-Solubility
n11:271B5E52-363D-11E5-9242-09173F13E4C5
n7:logP
n11:271B5E50-363D-11E5-9242-09173F13E4C5 n11:271B5E53-363D-11E5-9242-09173F13E4C5 n11:271B5E6A-363D-11E5-9242-09173F13E4C5
n7:logS
n11:271B5E51-363D-11E5-9242-09173F13E4C5
n5:hasATCCode
n32:N04BX02
n7:H-Bond-Acceptor-Count
n11:271B5E60-363D-11E5-9242-09173F13E4C5
n7:H-Bond-Donor-Count
n11:271B5E61-363D-11E5-9242-09173F13E4C5
n7:InChIKey
n11:271B5E5B-363D-11E5-9242-09173F13E4C5
n7:Polar-Surface-Area--PSA-
n11:271B5E5C-363D-11E5-9242-09173F13E4C5
n7:Polarizability
n11:271B5E5E-363D-11E5-9242-09173F13E4C5
n7:Refractivity
n11:271B5E5D-363D-11E5-9242-09173F13E4C5
n7:Rotatable-Bond-Count
n11:271B5E5F-363D-11E5-9242-09173F13E4C5
n7:absorption
Entacapone is rapidly absorbed (approximately 1 hour). The absolute bioavailability following oral administration is 35%.
n7:affectedOrganism
Humans and other mammals
n7:casRegistryNumber
130929-57-6
n7:category
n7:clearance
* 850 mL/min
n7:containedIn
n29:271B5E4D-363D-11E5-9242-09173F13E4C5
n7:Bioavailability
n11:271B5E66-363D-11E5-9242-09173F13E4C5
n7:Ghose-Filter
n11:271B5E68-363D-11E5-9242-09173F13E4C5
n7:MDDR-Like-Rule
n11:271B5E69-363D-11E5-9242-09173F13E4C5
n7:Number-of-Rings
n11:271B5E65-363D-11E5-9242-09173F13E4C5
n7:Physiological-Charge
n11:271B5E64-363D-11E5-9242-09173F13E4C5
n7:Rule-of-Five
n11:271B5E67-363D-11E5-9242-09173F13E4C5
n7:Traditional-IUPAC-Name
n11:271B5E55-363D-11E5-9242-09173F13E4C5
n7:pKa--strongest-acidic-
n11:271B5E62-363D-11E5-9242-09173F13E4C5
n7:pKa--strongest-basic-
n11:271B5E63-363D-11E5-9242-09173F13E4C5