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Namespace Prefixes

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Statements

Subject Item
n2:DB05271
rdf:type
n3:Drug
n3:description
Rotigotine (Neupro) is a non-ergoline dopamine agonist indicated for the treatment of Parkinson's disease (PD) and restless legs syndrome (RLS) in Europe and the United States. It is formulated as a once-daily transdermal patch which provides a slow and constant supply of the drug over the course of 24 hours. Like other dopamine agonists, rotigotine has been shown to possess antidepressant effects and may be useful in the treatment of depression as well. Rotigotine was developed by Aderis Pharmaceuticals. In 1998, Aderis licensed worldwide development and commercialization rights for rotigotine to the German pharmaceutical company Schwarz Pharma (today a subsidiary of the Belgian company UCB S.A.). The drug has been approved by the EMEA for use in Europe in 2006 and is today being sold in several European countries. In 2007, the Neupro patch was approved by the Food and Drug Administration (FDA) as the first transdermal treatment of Parkinson's disease in the United States. However, as of 2008, Schwarz Pharma has recalled all Neupro patches in the United States and some in Europe because of problems with the delivery mechanism. Rotigotine has been authorized as a treatment for RLS since August 2008.
n3:dosage
n10:271B3FA6-363D-11E5-9242-09173F13E4C5 n10:271B3FA7-363D-11E5-9242-09173F13E4C5 n10:271B3FA8-363D-11E5-9242-09173F13E4C5 n10:271B3FA9-363D-11E5-9242-09173F13E4C5 n10:271B3FAF-363D-11E5-9242-09173F13E4C5 n10:271B3FB0-363D-11E5-9242-09173F13E4C5 n10:271B3FAA-363D-11E5-9242-09173F13E4C5 n10:271B3FAB-363D-11E5-9242-09173F13E4C5 n10:271B3FAC-363D-11E5-9242-09173F13E4C5 n10:271B3FAD-363D-11E5-9242-09173F13E4C5 n10:271B3FAE-363D-11E5-9242-09173F13E4C5 n10:271B3FB1-363D-11E5-9242-09173F13E4C5 n10:271B3FB2-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Giladi N, Boroojerdi B, Korczyn AD, Burn DJ, Clarke CE, Schapira AH: Rotigotine transdermal patch in early Parkinson's disease: A randomized, double-blind, controlled study versus placebo and ropinirole. Mov Disord. 2007 Oct 12;. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17935234 # Chen JJ, Swope DM, Dashtipour K, Lyons KE: Transdermal rotigotine: a clinically innovative dopamine-receptor agonist for the management of Parkinson's disease. Pharmacotherapy. 2009 Dec;29(12):1452-67. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19947805 # Perez-Lloret S, Rey MV, Ratti PL, Rascol O: Rotigotine transdermal patch for the treatment of Parkinson's Disease. Fundam Clin Pharmacol. 2013 Feb;27(1):81-95. doi: 10.1111/j.1472-8206.2012.01028.x. Epub 2012 Feb 9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22320451 # de Biase S, Merlino G, Lorenzut S, Valente M, Gigli GL: ADMET considerations for restless leg syndrome drug treatments. Expert Opin Drug Metab Toxicol. 2012 Oct;8(10):1247-61. doi: 10.1517/17425255.2012.708023. Epub 2012 Jul 18. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22808933
n3:group
approved
n3:halfLife
After removal of the patch, plasma levels decreased with a terminal half-life of 5 to 7 hours. The pharmacokinetic profile showed a biphasic elimination with an initial half-life of 3 hours.
n3:indication
For use/treatment in neurologic disorders and parkinson's disease as well as moderate-to-severe primary Restless Legs Syndrome.
owl:sameAs
n16:DB05271 n18:DB05271
dcterms:title
Rotigotine
adms:identifier
n9:Rotigotine n11:50474-801-03 n14:PA165958352 n19:57537 n20:99443232 n21:941 n22:D05768 n23:DB05271 n25:941 n26:50054062 n27:51867
n3:mechanismOfAction
Rotigotine, a member of the dopamine agonist class of drugs, is delivered continuously through the skin (transdermal) using a silicone-based patch that is replaced every 24 hours. A dopamine agonist works by activating dopamine receptors in the body, mimicking the effect of the neurotransmitter dopamine. The precise mechanism of action of rotigotine as a treatment for Restless Legs Syndrome is unknown but is thought to be related to its ability to stimulate dopamine
n3:patent
n5:6884434
n3:routeOfElimination
Urine (71%), Fecal (23%). Most of rotigotine that is excreted in the urine is in the form of inactive conjugates. Unchanged drug made up less <1%.
n3:toxicity
The most likely symptoms of overdose would be those related to the pharmacodynamic profile of a dopamine agonist, including nausea, vomiting, hypotension, involuntary movements, hallucinations, confusion, convulsions, and other signs of excessive dopaminergic stimulation.
n3:volumeOfDistribution
The weight normalized apparent volume of distribution, (Vd/F), in humans is approximately 84 L/kg after repeated dose administration.
n3:foodInteraction
Because rotigotine is administered transdermally, food should not affect absorption, and the product may be administered without regard to the timing of meals.
n3:proteinBinding
92% in vitro and 89.5% in vivo.
n3:salt
n3:synthesisReference
Hans-Michael Wolff, Luc Quere, Jens Riedner, "NOVEL POLYMORPHIC FORM OF ROTIGOTINE AND PROCESS FOR PRODUCTION." U.S. Patent US20090143460, issued June 04, 2009.
foaf:page
n13:rotigotine-transdermal.html n24:neupro-drug.htm
n3:IUPAC-Name
n4:271B3FB7-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B3FBD-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B3FBC-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B3FB9-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B3FBA-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B3FBB-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B3FB5-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B3FCD-363D-11E5-9242-09173F13E4C5 n4:271B3FB6-363D-11E5-9242-09173F13E4C5 n4:271B3FB3-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B3FB4-363D-11E5-9242-09173F13E4C5
n6:hasATCCode
n7:N04BC09
n3:H-Bond-Acceptor-Count
n4:271B3FC3-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B3FC4-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B3FBE-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B3FBF-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B3FC1-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B3FC0-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B3FC2-363D-11E5-9242-09173F13E4C5
n3:absorption
Bioavailability varies depending on the application site. Differences in bioavailability were very small between the abdomen and hip (<1%). In contrast, the shoulder and thigh had a very large different in measured bioavailability (46%), with the shoulder showing the higher value. Tmax, 8 mg dose = 15 - 18 hours (it take approximately 3 hours until rotigotine reaches detectable levels in the plasma). The peak concentration cannot be observered. Steady state is reached in 2-3 days.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
92206-54-7
n3:category
n3:Bioavailability
n4:271B3FC9-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B3FCB-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B3FCC-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B3FC8-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B3FC7-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B3FCA-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B3FB8-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B3FC5-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B3FC6-363D-11E5-9242-09173F13E4C5