T3D2577

2618 T3D2577

Varenicline

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. 249296-44-4

5310966

C13H13N3

211.110950 Solid (A308).

8.77e-02 g/L

Ingestion (A308)

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.

Metabolism is limited (<10%). Most of the active compound is excreted renally (81%). A small proportion is glucuronidated, oxidated, N-formylated or conjugated to a hexose. 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 (MSDS, A308). Route of Elimination: 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. Half Life: The elimination half-life of varenicline is approximately 24 hours No indication of carcinogenicity to humans (not listed by IARC).

For use as an aid in smoking cessation (A308).

Some disorders may include anemia, lymphadenopathy, angina pectoris, arrhythmia, bradycardia, ventricular extrasystoles, myocardial infarction, palpitations, tachycardia, deafness, meniere's disease, dhyroid gland disorders, conjunctivitis, acquired night blindness, blindness transient, cataract subcapsular, gastric ulcer, intestinal obstruction, pancreatitis acute, chest pain, influenza like illness, edema, diabetes mellitus, facial palsy, mental impairment, multiple sclerosis, polyuria, and menstrual disorder.(A308).

Nausea, sleep disturbance, constipation, flatulence, and vomiting. In case of overdose, standard supportive measures should be instituted as required. (L1712)

2009-07-05T03:36:25Z

2014-12-24T20:25:43Z

Varenicline

DB01273

true

[H][C@]12C[C@]([H])(CNC1)C1=CC3=C(C=C21)N=CC=N3

C13H13N3

InChI=1/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/t8-,9+

InChIKey=JQSHBVHOMNKWFT-DTORHVGONA-N

211.2624

211.110947431

Exogenous Solid 0.9

HMDB15398

CHEMBL1396

4470510

Vinod Kumar Kansal, Suhail Ahmad, Amit Gupta, “PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF.” U.S. Patent US20090318695, issued December 24, 2009.