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Namespace Prefixes

PrefixIRI
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n12http://linked.opendata.cz/resource/drugbank/drug/DB04844/identifier/chebi/
n23http://linked.opendata.cz/resource/atc/
n22http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB04844
rdf:type
n3:Drug
n3:description
A drug formerly used as an antipsychotic but now used primarily in the symptomatic treatment of various hyperkinetic disorders. It is a monoamine depletor and used as symptomatic treatment of chorea associated with Huntington's disease. FDA approved on August 15, 2008.
n3:dosage
n4:271B5936-363D-11E5-9242-09173F13E4C5 n4:271B5937-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9040721 # Guay DR: Tetrabenazine, a monoamine-depleting drug used in the treatment of hyperkinetic movement disorders. Am J Geriatr Pharmacother. 2010 Aug;8(4):331-73. doi: 10.1016/j.amjopharm.2010.08.006. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20869622
n3:group
approved
n3:halfLife
α-HTBZ = 7 hours; β-HTBZ = 5 hours; 9-desmethyl-β-DHTBZ = 12 hours.
n3:indication
Treatment of hyperkinetic movement disorders like chorea in Huntington's disease, hemiballismus, senile chorea, Tourette syndrome and other tic disorders, and tardive dyskinesia
owl:sameAs
n15:DB04844 n19:DB04844
dcterms:title
Tetrabenazine
adms:identifier
n9:Tetrabenazine n10:D08575 n11:PA140222719 n12:9467 n21:6018 n25:46506426 n26:C11168 n27:67386-421-01 n28:DB04844 n29:50017701 n30:5796
n3:mechanismOfAction
Tetrabenazine is a reversible human vesicular monoamine transporter type 2 inhibitor (Ki = 100 nM). It acts within the basal ganglia and promotes depletion of monoamine neurotransmitters serotonin, norepinephrine, and dopamine from stores. It also decreases uptake into synaptic vesicles. Dopamine is required for fine motor movement, so the inhibition of its transmission is efficacious for hyperkinetic movement. Tetrabenazine exhibits weak in vitro binding affinity at the dopamine D2 receptor (Ki = 2100 nM).
n3:packager
n20:271B5932-363D-11E5-9242-09173F13E4C5 n20:271B5933-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
After oral administration, tetrabenazine is extensively hepatically metabolized, and the metabolites are primarily renally eliminated (75%). Tetrabenazine is also cleared fecally (7% to 16%). Unchanged tetrabenazine has not been found in human urine. Urinary excretion of α-HTBZ or β-HTBZ (the major metabolites) accounted for less than 10% of the administered dose.
n3:synonym
2-oxo-3-Isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bh-benzo[a]quinolizine 1,2,4,6,7,11b-hexahydro-3-Isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one Tetrabenazina Tetrabenzaine Tetrabenzine 2-oxo-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizine TBZ Tetrabenazinum Tetra benazin
n3:toxicity
Dose-limiting adverse effects are sedation, parkinsonism, akathsia, and depression. LD50 oral, mouse: 550 mg/kg
n3:volumeOfDistribution
Steady State, IV, in HD or tardive dyskinesia patients: 385L. Tetrabenazine is rapidly distributed to the brain following IV injection. The site with the highest binding is the striatum, while the lowest binding was observed in the cortex.
n3:proteinBinding
Tetrabenazine = 82 - 88%; α-HTBZ = 60 - 68%; β-HTBZ = 59 - 63%.
n3:synthesisReference
Michael James Rishel, Kande Kankananamalage Dayarathna Amarasinghe, Sean Richard Dinn, Bruce Fletcher Johnson, "METHOD FOR MAKING TETRABENAZINE COMPOUNDS." U.S. Patent US20080306267, issued December 11, 2008.
n5:hasConcept
n6:M0021208
foaf:page
n18:xenazine-drug.htm n24:tetrabenazine.html
n3:IUPAC-Name
n7:271B593C-363D-11E5-9242-09173F13E4C5
n3:InChI
n7:271B5942-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n7:271B5941-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n7:271B593E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n7:271B593F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n7:271B5940-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n7:271B5952-363D-11E5-9242-09173F13E4C5 n7:271B593A-363D-11E5-9242-09173F13E4C5
n3:logP
n7:271B5938-363D-11E5-9242-09173F13E4C5 n7:271B593B-363D-11E5-9242-09173F13E4C5
n3:logS
n7:271B5939-363D-11E5-9242-09173F13E4C5
n3:pKa
n7:271B5954-363D-11E5-9242-09173F13E4C5
n22:hasATCCode
n23:N07XX06
n3:H-Bond-Acceptor-Count
n7:271B5948-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n7:271B5949-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n7:271B5943-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n7:271B5944-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n7:271B5946-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n7:271B5945-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n7:271B5947-363D-11E5-9242-09173F13E4C5
n3:absorption
Following oral administration of tetrabenazine, the extent of absorption is at least 75%. After single oral doses ranging from 12.5 to 50 mg, plasma concentrations of tetrabenazine are generally below the limit of detection because of the rapid and extensive hepatic metabolism of tetrabenazine. Food does not affect the absorption of tetrabenazine. Cmax, oral = 4.8 ng/mL in HD or tardive dyskinesia patients; Tmax, oral = 69 min in HD or tardive dyskinesia patients
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
58-46-8
n3:category
n3:clearance
IV, 1.67 L/min in HD or tardive dyskinesia patients
n3:containedIn
n16:271B5934-363D-11E5-9242-09173F13E4C5 n16:271B5935-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n7:271B594E-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n7:271B5950-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n7:271B5951-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n7:271B5953-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n7:271B594D-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n7:271B594C-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n7:271B594F-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n7:271B593D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n7:271B594A-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n7:271B594B-363D-11E5-9242-09173F13E4C5