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Namespace Prefixes

PrefixIRI
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n9http://linked.opendata.cz/resource/drugbank/drug/DB09028/identifier/chebi/
n14http://bio2rdf.org/drugbank:
n6http://linked.opendata.cz/resource/drugbank/drug/DB09028/identifier/wikipedia/
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n7http://linked.opendata.cz/resource/drugbank/drug/DB09028/identifier/kegg-compound/
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n12http://www.drugs.com/international/
n10http://linked.opendata.cz/resource/drugbank/drug/DB09028/identifier/drugbank/

Statements

Subject Item
n2:DB09028
rdf:type
n3:Drug
n3:description
Cytisine is an alkaloid that is found naturally in several plant genera such as Laburnum and Cytisus of the family Fabaceae. Recent studies have shown it to be a more effective and significantly more affordable smoking cessation treatment than nicotine replacement therapy. Also known as baptitoxine or sophorine, cytisine has been used as a smoking cessation treatment since 1964, and is relatively unknown in regions outside of central and Eastern Europe. Cytisine is a partial nicotinic acetylcholine agonist with a half-life of 4.8 hours. Recent Phase III clinical trials using Tabex (a brand of Cytisine marketed by Sopharma AD) have shown similar efficacy to varenicline, but at a fraction of the cost.
n3:generalReferences
# Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, Parag V, Bassett B, Bullen C: Cytisine versus nicotine for smoking cessation. N Engl J Med. 2014 Dec 18;371(25):2353-62. doi: 10.1056/NEJMoa1407764. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/25517706 # http://www.tabex.net/tabex-patient-use-details.php # Houlihan LM, Slater Y, Guerra DL, Peng JH, Kuo YP, Lukas RJ, Cassels BK, Bermudez I: Activity of cytisine and its brominated isosteres on recombinant human alpha7, alpha4beta2 and alpha4beta4 nicotinic acetylcholine receptors. J Neurochem. 2001 Sep;78(5):1029-43. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11553677 # Tutka P, Zatonski W: Cytisine for the treatment of nicotine addiction: from a molecule to therapeutic efficacy. Pharmacol Rep. 2006 Nov-Dec;58(6):777-98. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17220536 # Cooper JC, Gutbrod O, Witzemann V, Methfessel C: Pharmacology of the nicotinic acetylcholine receptor from fetal rat muscle expressed in Xenopus oocytes. Eur J Pharmacol. 1996 Aug 15;309(3):287-98. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8874153
n3:group
approved investigational
n3:halfLife
4.8 hours.
n3:indication
Indicated for use in smoking cessation.
owl:sameAs
n14:DB09028
dcterms:title
Cytisine
adms:identifier
n6:Cytisine n7:C10763 n8:D07770 n9:4055 n10:DB09028
n3:mechanismOfAction
Cytisine is a low efficacy partial agonist of ⍺4-β2 nicotinic acetylcholine receptors. These which are believed to be central to the effect of nicotine (NIC) on the reward pathway and facilitate addiction. Cytisine reduces the effects of NIC on dopamine release in the mesolimbic system when given alone, while simultaneously attenuating NIC withdrawal symptoms that accompany cessation attempts.
n3:synonym
Sophorine Ulexin (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one Baptitoxine
n3:toxicity
The therapeutic index of cytisine is wide. -Large doses can interfere with breathing and cause death. From MSDS: orl-mus LD50:101 mg/kg ipr-mus LD50:8550 ug/kg ivn-mus LD50:1730 ug/kg scu-rat LD50:8750 ug/kg
n3:volumeOfDistribution
Oral: 6.2 l/kg Oral (5 mg/kg; tested in rabbits).
n3:synthesisReference
ORGANIC SYNTHESES, 2006, 83, 141. "Synthesis of (+)-(1R,@S,9S)-11-Methyl-7,11-Diazatricyclo[7.3.1.02.7]tridecane, a (+)sparteine surrogate," DOI: 10.15227/orgsyn.083.0141
foaf:page
n12:cytisine.html
n3:IUPAC-Name
n4:271B3ECD-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B3ED3-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B3ED2-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B3ECF-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B3ED0-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B3ED1-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B3ECB-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B3EC9-363D-11E5-9242-09173F13E4C5 n4:271B3ECC-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B3ECA-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B3ED9-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B3EDA-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B3ED4-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B3ED5-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B3ED7-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B3ED6-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B3ED8-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
485-35-8
n3:clearance
Renal: 43 mL/min.
n3:Bioavailability
n4:271B3EDE-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n4:271B3EE3-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B3EE0-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B3EE1-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B3EE2-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B3EDD-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B3EDC-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B3EDF-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B3ECE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B3EDB-363D-11E5-9242-09173F13E4C5