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Namespace Prefixes

PrefixIRI
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n19http://www.drugs.com/ppa/
n22http://www.rxlist.com/
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n20http://linked.opendata.cz/ontology/sukl/drug/
n25http://linked.opendata.cz/resource/atc/
n6http://linked.opendata.cz/resource/drugbank/drug/DB04855/identifier/pubchem-substance/

Statements

Subject Item
n2:DB04855
rdf:type
n3:Drug
n3:description
Dronedarone is a sinus rhythm controller for management of paroxysmal or persistent atrial fibrillation. Classified as a Class III antiarrhythmic but displays properties of all four Vaughan-Williams classes, dronedarone blocks a multitude of channels (sodium, potassium, calcium), and demonstrates antiadrenergic properties. Chemically, it is a benzofuran derivative. FDA approved on July 1, 2009.
n3:dosage
n24:271B59EE-363D-11E5-9242-09173F13E4C5 n24:271B59EF-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Dale KM, White CM: Dronedarone: an amiodarone analog for the treatment of atrial fibrillation and atrial flutter. Ann Pharmacother. 2007 Apr;41(4):599-605. Epub 2007 Mar 27. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17389667 # Iwamoto T, Watanabe Y, Kita S, Blaustein MP: Na+/Ca2+ exchange inhibitors: a new class of calcium regulators. Cardiovasc Hematol Disord Drug Targets. 2007 Sep;7(3):188-98. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17896959 # Celestino D, Medei E, Moro S, Elizari MV, Sicouri S: Acute in vitro effects of dronedarone, an iodine-free derivative, and amiodarone, on the rabbit sinoatrial node automaticity: a comparative study. J Cardiovasc Pharmacol Ther. 2007 Sep;12(3):248-57. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17875953 # Pamukcu B, Lip GY: Dronedarone as a new treatment option for atrial fibrillation patients: pharmacokinetics, pharmacodynamics and clinical practice. Expert Opin Pharmacother. 2011 Jan;12(1):131-40. doi: 10.1517/14656566.2011.540800. Epub 2010 Dec 2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21126199 # De Ferrari GM, Dusi V: Drug safety evaluation of dronedarone in atrial fibrillation. Expert Opin Drug Saf. 2012 Nov;11(6):1023-45. doi: 10.1517/14740338.2012.722994. Epub 2012 Sep 13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22971242
n3:group
approved
n3:halfLife
Elimination half-life: 13-19 hours
n3:indication
Management of paroxysmal or persistent atrial fibrillation via restoration of normal sinus rhythm.
owl:sameAs
n11:DB04855
dcterms:title
Dronedarone
adms:identifier
n6:14861729 n7:Dronedarone n8:PA153619853 n9:208898 n12:D02537 n13:54868-3086-0 n14:180996 n15:DB04855 n16:50659
n3:mechanismOfAction
The antiarrhythmic effect of dronedarone may be due to at least two major actions. It prolongs the duration of action potential and refractory period in myocardial tissue via inhibition of sodium and potassium channels. Via inhibition of calcium channels and blockage of beta1-adrenergic receptors, a decrease in AV conduction and sinus node function can be observed. Dronedarone can also cause an increase in blood pressure by inhibition of alpha1-adrenergic receptors.
n3:patent
n17:2294812 n17:2047773 n17:7323493 n17:5223510
n3:routeOfElimination
6% of the dose was excreted in the urine, mainly as metabolites (no unchanged compound excreted in urine), and 84% was excreted in feces, mainly as metabolites.
n3:synonym
N-(2-Butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)-methanesulfonamide SR 33589 SR 33589b N-(2-Butyl-3-(P-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)methanesulfonamide Multaq
n3:toxicity
Most common adverse reactions (≥2%) are diarrhea, nausea, abdominal pain, vomiting, and asthenia.
n3:volumeOfDistribution
When intravenously administered, the volume of distribution is 1400 L.
n20:hasAHFSCode
n21:24-04-04-20
n3:foodInteraction
Do not take dronedarone with grapefruit juice. Grapefruit juice is a potent CYP3A4 inhibitor which will increase serum concentrations of dronedarone threefold Absorption of dronedarone increases 3-fold if taken with food especially if meal is high in fat content
n3:proteinBinding
Dronedarone and its N-debutyl metabolite is >98% protein bound - mainly to albumin.
n3:salt
n3:synthesisReference
Arie Gutman, Gennadi Nisnevich, Lev Yudovitch, "Process for the preparation of dronedarone." U.S. Patent US20050049302, issued March 03, 2005.
foaf:page
n19:dronedarone.html n22:multaq-drug.htm
n3:IUPAC-Name
n4:271B59F4-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B59FA-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B59F9-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B59F6-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B59F7-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B59F8-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B59F2-363D-11E5-9242-09173F13E4C5 n4:271B5A0A-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B59F0-363D-11E5-9242-09173F13E4C5 n4:271B59F3-363D-11E5-9242-09173F13E4C5 n4:271B5A0B-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B59F1-363D-11E5-9242-09173F13E4C5
n20:hasATCCode
n25:C01BD07
n3:H-Bond-Acceptor-Count
n4:271B5A00-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5A01-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B59FB-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B59FC-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B59FE-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B59FD-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B59FF-363D-11E5-9242-09173F13E4C5
n3:absorption
Because of presystemic first pass metabolism the absolute bioavailability of dronedarone without food is low, about 4%. It increases to approximately 15% when dronedarone is administered with a high fat meal. After oral administration in fed conditions, peak plasma concentrations of dronedarone and the main circulating active metabolite (N-debutyl metabolite) are reached within 3 to 6 hours. After repeated administration of 400 mg twice daily, steady state is reached within 4 to 8 days of treatment. The steady state Cmax and exposure of the main N-debutyl metabolite is similar to that of the parent compound.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
141626-36-0
n3:category
n3:clearance
Plasma clearance = 130-150 L/h.
n3:Bioavailability
n4:271B5A06-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5A08-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5A09-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5A05-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5A04-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5A07-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B59F5-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5A02-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5A03-363D-11E5-9242-09173F13E4C5