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Namespace Prefixes

PrefixIRI
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n20http://www.rxlist.com/
n13http://linked.opendata.cz/resource/drugbank/drug/DB06204/identifier/wikipedia/
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n14http://linked.opendata.cz/resource/drugbank/patent/
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n8http://linked.opendata.cz/resource/drugbank/drug/DB06204/identifier/national-drug-code-directory/
n22http://linked.opendata.cz/resource/atc/
n21http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB06204
rdf:type
n3:Drug
n3:description
Opioid analgesic for treatment of moderate to severe pain. FDA approved on Nov 20, 2008.
n3:dosage
n4:271B49F6-363D-11E5-9242-09173F13E4C5 n4:271B49F7-363D-11E5-9242-09173F13E4C5 n4:271B49F8-363D-11E5-9242-09173F13E4C5 n4:271B49F9-363D-11E5-9242-09173F13E4C5 n4:271B49FA-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Tzschentke TM, Christoph T, Kogel B, Schiene K, Hennies HH, Englberger W, Haurand M, Jahnel U, Cremers TI, Friderichs E, De Vry J: (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol hydrochloride (tapentadol HCl): a novel mu-opioid receptor agonist/norepinephrine reuptake inhibitor with broad-spectrum analgesic properties. J Pharmacol Exp Ther. 2007 Oct;323(1):265-76. Epub 2007 Jul 26. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17656655 # Gohler K, Brett M, Smit JW, Rengelshausen J, Terlinden R: Comparative pharmacokinetics and bioavailability of tapentadol following oral administration of immediate- and prolonged-release formulations. Int J Clin Pharmacol Ther. 2013 Apr;51(4):338-48. doi: 10.5414/CP201722. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23357834 # Xu XS, Smit JW, Lin R, Stuyckens K, Terlinden R, Nandy P: Population pharmacokinetics of tapentadol immediate release (IR) in healthy subjects and patients with moderate or severe pain. Clin Pharmacokinet. 2010 Oct;49(10):671-82. doi: 10.2165/11535390-000000000-00000. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20818833
n3:group
approved
n3:halfLife
Elimination half-life, IV: 4 hours.
n3:indication
The immediate-release formulation of tapentadol is indicated for the relief of moderate to severe acute pain. The long-acting formulation serves as a continuous, around-the-clock analgesic that is indicated for the relief of moderate to severe chronic pain or neuropathic pain associated with diabetic peripheral neuropathy.
owl:sameAs
n12:DB06204
dcterms:title
Tapentadol
adms:identifier
n6:D06007 n8:35356-525-30 n9:8013742 n10:DB06204 n13:Tapentadol n15:9838022 n16:47207665
n3:mechanismOfAction
Tapendadol causes large increases in levels of extracellular norepinephrine (NE) due to a dual mechanism of action involving mu opioid receptor (MOR) agonism as well as noradrenaline reuptake inhibition.
n3:patent
n14:6071970 n14:RE39593
n3:routeOfElimination
Tapentadol and its metabolites are excreted almost exclusively (99%) via the kidneys. Approximately 70% (55% O-glucuronide and 15% sulfate of tapentadol) is excreted in conjugated form. A total of 3% of drug was excreted in urine as unchanged drug.
n3:synonym
BN-200 Nucynta Tapentadol CG-5503
n3:toxicity
Oral, rabbit: LD50 = 3200 mg/kg; Oral, mouse: LD50 = 300 mg/kg; Oral, rat: LD50: 980 mg/kg; The most common reasons for discontinuation due to adverse events were dizziness, nausea, vomiting, somnolence, and headache.
n3:volumeOfDistribution
Following IV administration, volume of distribution is 540 ± 98 L.
n3:foodInteraction
Food increases the AUC and Cmax of tapentadol. Despite this, tapentadol can be given without regards to food.
n3:proteinBinding
~20%
n3:salt
n3:synthesisReference
Giuseppe Motta, Domenico Vergani, Giorgio Bertolini, "PROCESS FOR THE PREPARATION OF TAPENTADOL AND INTERMEDIATES THEREOF." U.S. Patent US20120232306, issued September 13, 2012.
foaf:page
n19:tapentadol-hydrochloride.html n20:nucynta-drug.htm
n3:IUPAC-Name
n7:271B49FF-363D-11E5-9242-09173F13E4C5
n3:InChI
n7:271B4A05-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n7:271B4A04-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n7:271B4A01-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n7:271B4A02-363D-11E5-9242-09173F13E4C5
n3:SMILES
n7:271B4A03-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n7:271B49FD-363D-11E5-9242-09173F13E4C5
n3:logP
n7:271B49FE-363D-11E5-9242-09173F13E4C5 n7:271B4A15-363D-11E5-9242-09173F13E4C5 n7:271B49FB-363D-11E5-9242-09173F13E4C5
n3:logS
n7:271B49FC-363D-11E5-9242-09173F13E4C5
n3:pKa
n7:271B4A16-363D-11E5-9242-09173F13E4C5
n21:hasATCCode
n22:N02AX06
n3:H-Bond-Acceptor-Count
n7:271B4A0B-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n7:271B4A0C-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n7:271B4A06-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n7:271B4A07-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n7:271B4A09-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n7:271B4A08-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n7:271B4A0A-363D-11E5-9242-09173F13E4C5
n3:absorption
Bioavailability, immediate release (IR), 86 mg: 32%; Bioavailability, extended release (ER), 86 mg: 32%; Cmax, IR: 64.2 ng/mL; Cmax, ER: 22.5 ng/mL; T max, IR: 1.5 hours; T max, ER: 5.0 hours; Tapentadol accumulates following multiple repeat doses.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
175591-23-8
n3:clearance
Total clearance = 1530 ± 177 ml/min.
n3:Bioavailability
n7:271B4A11-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n7:271B4A13-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n7:271B4A14-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n7:271B4A10-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n7:271B4A0F-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n7:271B4A12-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n7:271B4A00-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n7:271B4A0D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n7:271B4A0E-363D-11E5-9242-09173F13E4C5