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Namespace Prefixes

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Statements

Subject Item
n2:DB01273
rdf:type
n3:Drug
n3:description
Varenicline is a prescription medication used to treat smoking addiction. This medication is the first approved nicotinic receptor partial agonist. Specifically, varenicline is a partial agonist of the alpha4/beta2 subtype of the nicotinic acetylcholine receptor. In addition it acts on alpha3/beta4 and weakly on alpha3beta2 and alpha6-containing receptors. A full agonism was displayed on alpha7-receptors. On March 9, 2015, the U.S. Food and Drug Administration warned that Varenicline, in the form of Pfizer Inc's quit-smoking drug, Chantix, has been associated with seizures and that some patients who drink while taking the drug may become aggressive or black out. Pfizer is conducting an additional safety study of the drug, results of which are expected in late 2015. The FDA said it is keeping the black box in place at least until the results of the trial are announced.
n3:dosage
n4:271B61C8-363D-11E5-9242-09173F13E4C5 n4:271B61C9-363D-11E5-9242-09173F13E4C5 n4:271B61CA-363D-11E5-9242-09173F13E4C5 n4:271B61CB-363D-11E5-9242-09173F13E4C5 n4:271B61CC-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Jorenby DE, Hays JT, Rigotti NA, Azoulay S, Watsky EJ, Williams KE, Billing CB, Gong J, Reeves KR: Efficacy of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, vs placebo or sustained-release bupropion for smoking cessation: a randomized controlled trial. JAMA. 2006 Jul 5;296(1):56-63. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16820547 # Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16766716 # Obach RS, Reed-Hagen AE, Krueger SS, Obach BJ, O'Connell TN, Zandi KS, Miller S, Coe JW: Metabolism and disposition of varenicline, a selective alpha4beta2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos. 2006 Jan;34(1):121-30. Epub 2005 Oct 12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16221753 # Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD 3rd, O'Neill BT: Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem. 2005 May 19;48(10):3474-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15887955 # Kuehn BM: FDA speeds smoking cessation drug review. JAMA. 2006 Feb 8;295(6):614. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16467225
n3:group
investigational approved
n3:halfLife
The elimination half-life of varenicline is approximately 24 hours
n3:indication
For use as an aid in smoking cessation.
owl:sameAs
n9:DB01273 n26:DB01273
dcterms:title
Varenicline
adms:identifier
n11:46505502 n14:0069-0471-97 n15:5310966 n16:4470510 n17:DB01273 n18:PA164781343 n23:Varenicline
n3:mechanismOfAction
Varenicline is an alpha-4 beta-2 neuronal nicotinic acetylcholine receptor partial agonist. The drug shows high selectiviyty for this receptor subclass, relative to other nicotinic receptors (>500-fold alpha-3 beta-4, >3500-fold alpha-7, >20,000-fold alpha-1 beta gamma delta) or non-nicotinic receptors and transporters (>2000-fold). The drug competitively inhibits the ability of nicotine to bind to and activate the alpha-4 beta-2 receptor. The drug exerts mild agonistic activity at this site, though at a level much lower than nicotine; it is presumed that this activation eases withdrawal symptoms.
n3:packager
n6:271B61BE-363D-11E5-9242-09173F13E4C5 n6:271B61BF-363D-11E5-9242-09173F13E4C5 n6:271B61BC-363D-11E5-9242-09173F13E4C5 n6:271B61BD-363D-11E5-9242-09173F13E4C5 n6:271B61C0-363D-11E5-9242-09173F13E4C5 n6:271B61C1-363D-11E5-9242-09173F13E4C5 n6:271B61C2-363D-11E5-9242-09173F13E4C5
n3:patent
n20:6410550 n20:7265119 n20:2525874 n20:2316921
n3:routeOfElimination
Varenicline undergoes minimal metabolism, with 92% excreted unchanged in the urine. Renal elimination of varenicline is primarily through glomerular filtration along with active tubular secretion possibly via the organic cation transporter, OCT2.
n3:synonym
CP-526,555
n3:proteinBinding
Less than 20%.
n3:salt
n3:synthesisReference
Vinod Kumar Kansal, Suhail Ahmad, Amit Gupta, "PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF." U.S. Patent US20090318695, issued December 24, 2009.
n21:hasConcept
n22:M0485421
foaf:page
n25:chantix.htm n27:varenicline.html
n3:IUPAC-Name
n5:271B61D1-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B61D7-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B61D6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B61D3-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B61D4-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B61D5-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B61CF-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B61E6-363D-11E5-9242-09173F13E4C5 n5:271B61CD-363D-11E5-9242-09173F13E4C5 n5:271B61D0-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B61CE-363D-11E5-9242-09173F13E4C5
n12:hasATCCode
n13:N07BA03
n3:H-Bond-Acceptor-Count
n5:271B61DD-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B61DE-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B61D8-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B61D9-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B61DB-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B61DA-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B61DC-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
249296-44-4
n3:category
n3:containedIn
n7:271B61C7-363D-11E5-9242-09173F13E4C5 n7:271B61C5-363D-11E5-9242-09173F13E4C5 n7:271B61C6-363D-11E5-9242-09173F13E4C5 n7:271B61C3-363D-11E5-9242-09173F13E4C5 n7:271B61C4-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B61E2-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B61E4-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B61E5-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B61E1-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B61E0-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B61E3-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B61D2-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B61DF-363D-11E5-9242-09173F13E4C5