{"ATC Code":"S - Sensory organs","Abbreviation":"","Aliases":["Ncgc00247735-01","Ncgc00247735-02","Vareniclin","Varenicline?","CP 526555; Champix; Chantix","s6985","CS-0396","DB01273","SB17430","Ncgc00247735-03"],"Biological Half-Life":"The elimination half-life of varenicline is approximately 24 hours","CAS":"249296-44-4","ChEMBL":"CHEMBL556954","ChemicalClasses":[],"Classes":null,"Decomposition":"Hazardous decomposition products: Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)","Dosing Info":[],"Drug Classes":"Breast Feeding; Lactation; Milk, Human; Nicotinic Agonists","Drug Indication":"For use as an aid in smoking cessation.  Varenicline as a nasal spray is indicated for the symptomatic treatment of dry eye disease.","Drug Warnings":"/BOXED WARNING/ WARNING: SERIOUS NEUROPSYCHIATRIC EVENTS. Serious neuropsychiatric events including, but not limited to, depression, suicidal ideation, suicide attempt, and completed suicide have been reported in patients taking CHANTIX. Some reported cases may have been complicated by the symptoms of nicotine withdrawal in patients who stopped smoking. Depressed mood may be a symptom of nicotine withdrawal. Depression, rarely including suicidal ideation, has been reported in smokers undergoing a smoking cessation attempt without medication. However, some of these symptoms have occurred in patients taking CHANTIX who continued to smoke.  All patients being treated with CHANTIX should be observed for neuropsychiatric symptoms including changes in behavior, hostility, agitation, depressed mood, and suicide-related events, including ideation, behavior, and attempted suicide. These symptoms, as well as worsening of pre-existing psychiatric illness and completed suicide, have been reported in some patients attempting to quit smoking while taking CHANTIX in the postmarketing experience. When symptoms were reported, most were during CHANTIX treatment, but some were following discontinuation of CHANTIX therapy.  These events have occurred in patients with and without pre-existing psychiatric disease. Patients with serious psychiatric illness such as schizophrenia, bipolar disorder, and major depressive disorder did not participate in the premarketing studies of CHANTIX.  Advise patients and caregivers that the patient should stop taking CHANTIX and contact a healthcare provider immediately if agitation, hostility, depressed mood, or changes in behavior or thinking that are not typical for the patient are observed, or if the patient develops suicidal ideation or suicidal behavior. In many postmarketing cases, resolution of symptoms after discontinuation of CHANTIX was reported, although in some cases the symptoms persisted; therefore, ongoing monitoring and supportive care should be provided until symptoms resolve.  The risks of CHANTIX should be weighed against the benefits of its use. CHANTIX has been demonstrated to increase the likelihood of abstinence from smoking for as long as one year compared to treatment with placebo. The health benefits of quitting smoking are immediate and substantial.","DrugClasses":[],"DurationOfAction":"","EliminationHalfLife":"24 hours","European Community (EC) Number":"810-384-9","FDA Pharmacological Classification":"W6HS99O8ZO","HeavyAtomCount":16,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Nicotinic Agonists","IUPACName":"5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene","InChI":"InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2","InChIKey":"JQSHBVHOMNKWFT-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003e","MolecularWeight":"211.26 g/mol","Pharmacodynamics":"Varenicline is a partial nicotinic acetylcholine receptor agonist, designed to partially activate this system while displacing nicotine at its sites of action in the brain.","PubChemId":170361,"Record 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.","Varenicline is a Partial Cholinergic Nicotinic Agonist and Cholinergic Receptor Agonist. The mechanism of action of varenicline is as a Partial Cholinergic Nicotinic Agonist and Cholinergic Agonist.","Varenicline is a partial agonist of the nicotinic acetylcholine receptor and is used to help in smoking cessation. Varenicline has been associated with a low rate of serum enzyme elevations during therapy and, since approval and its widescale use, with rare instances of clinically apparent mild liver injury.","Varenicline is a partial agonist of the nicotinic acetylcholine receptor (nAChR) subtype alpha4beta2. Nicotine stimulation of central alpha4beta2 nAChRs located at presynaptic terminals in the nucleus accumbens causes the release of the neurotransmitter dopamine, which may be associated with the experience of pleasure; nicotine addiction constitutes a physiologic dependence related to this dopaminergic reward system. As an AChR partial agonist, varenicline attenuates the craving and withdrawal symptoms that occur with abstinence from nicotine but is not habit-forming itself.","A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION.","See also: Varenicline (annotation moved to)."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Varenicline","Name":"Varenicline","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q411330","Name":"Varenicline","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01273","Name":"Varenicline","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/170361","Name":"Varenicline","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL556954","Name":"Varenicline","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=249296-44-4","Name":"Varenicline","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D08669","Name":"Varenicline","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID40861516","Name":"Varenicline","Sub":false}]}],"SMILES":"C1C2CNCC1C3=CC4=NC=CN=C4C=C23","Scheduling":[{"gov":"Canada","schedule":"prescription only substance"},{"gov":"United Kingdom","schedule":"prescription only substance"},{"gov":"United States","schedule":"prescription only substance"},{"gov":"European Union","schedule":"prescription only substance"}],"Stability/Shelf Life":"Stable under recommended storage conditions.","StructureBase64":"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Effects":null,"Therapeutic Uses":"Nicotinic Agonists","Title":"Varenicline","Wikidata":"Q411330","Wikipedia":"Varenicline","XLogP":0.8}