Compound: Varenicline
SMILES: n1c2c(ncc1)cc3[C@H]4CNC[C@@H](c3c2)C4
InChIKey: JQSHBVHOMNKWFT-DTORHVGOSA-N
Synonyms: Varenicline, vareniclina, vareniclinum, CP 526555, CP-526,555, W6HS99O8ZO, CP-526555, CHEBI:84500, 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine, (1R,12S)-5,8,14-triazatetracyclo[10.3.1.0^{2,11}.0^{4,9}]hexadeca-2(11),3,5,7,9-pentaene, 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine, DTXSID40861516, DTXSID70891447, (1R,12S)-5,8,14-triazatetracyclo(10.3.1.0^(2,11).0^(4,9))hexadeca-2(11),3,5,7,9-pentaene, RefChem:58779, 6,7,8,9-tetrahydro-6,10-methano-6H-pyrazino(2,3-h)benzazepine, DTXCID80197326, N07BA03, DTXCID101030560, (1R,12S)-5,8,14-triazatetracyclo(10.3.1.02,11.04,9)hexadeca-2,4,6,8,10-pentaene, 7,8,9,10-tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine (2R,3R)-2,3-dihydroxybutqanedioate, 810-384-9, 249296-44-4, 6,10-Methano-6H-pyrazino(2,3-h)(3)benzazepine, 7,8,9,10-tetrahydro-, 7,8,9,10-tetrahydro-6H-6,10-methanoazepino(4,5-g)quinoxaline, (6R,10S)-7,8,9,10-tetrahydro-6H-6,10-methanoazepino[4,5-g]quinoxaline, VARENICLINE [INN], Varenicline [INN:BAN], UNII-W6HS99O8ZO, Champix;, HSDB 7591, 6,10-Methano-6H-pyrazino[2,3-h][3]benzazepine, 7,8,9,10-tetrahydro-; 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine; CP 526555; Champix; Chantix; Varenicline, MFCD10001497, Varenicline Impurity 38, VARENICLINE [MI], VARENICLINE [HSDB], VARENICLINE [VANDF], VARENICLINE [MART.], US9284322, varenicline, VARENICLINE [WHO-DD], SCHEMBL137144, VARENICLINE [EMA EPAR], GTPL5459, CHEMBL1076903, SCHEMBL29710884, BDBM221048, EBC-47146, NSC772250, AKOS024457790, AC-9008, NSC-772250, compound 9a [PMID: 16171993], AS-16357, EN300-761457, Q411330, BRD-K18855837-046-01-4, (1S,12R)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene, REL-(6R,10S)-7,8,9,10-TETRAHYDRO-6H-6,10-METHANOAZEPINO[4,5-G]QUINOXALINE
Theoretical properties:
molecular_formula: C13H13N3
molecular_weight: 211.26 g/mol
exact_mass: 211.110947427 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 16
topological_polar_surface_area: 37.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 8.77e-02 g/L
Descriptions:
pubchem: Varenicline is an organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking. It has a role as a serotonergic agonist and a nicotinic acetylcholine receptor agonist. It is a bridged compound, an organic heterotetracyclic compound and a secondary amino compound. It is a conjugate base of a varenicline(1+).
chebi: An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking.
chembl: VARENICLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Varenicline, sold under the brand names Chantix and Champix among others, is a medication used for smoking cessation and for the treatment of dry eye syndrome. It is a nicotinic acetylcholine receptor partial agonist. When activated, this receptor leads to the release of dopamine in the nucleus accumbens, the brain's reward center, thereby reducing cravings and withdrawal symptoms with smoking cessation, although less pronounced than a full agonist (e.g. nicotine).
Common side effects include nausea, insomnia, abnormal dreams, headache, and nasopharyngitis (inflammation of the nose and throat). Despite these potential adverse effects, varenicline has proven efficacy in helping individuals quit smoking. It is estimated that approximately one in eleven smokers who use varenicline successfully remain abstinent from tobacco at six months.
It is on the World Health Organization's List of Essential Medicines. The medication is available as a generic medication. In the United States, varenicline was prescribed over 1 million times in 2020, ranking as the 275th most commonly prescribed medication.