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Varenicline
Varenicline
Synonyms CP-526555-18
Brand names Champix, Chantix
IUPAC name

IUPAC name
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
ChemSpider

4470510

DrugBank

DB01273

PubChem

5310966

PDB fields

N/A

Formula

C13H13N3

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/t8-,9+
InChIKey
InChIKey
JQSHBVHOMNKWFT-DTORHVGOSA-N
SMILES
SMILES
C1[C@@H]2CNC[C@H]1C3=CC4=NC=CN=C4C=C2
(Jmol 3D structure)
Mol. mass

211.2624 g/mol

Varenicline is the single most effective smoking cessation aid.[1][2] It was synthesized from cytisine.[3] One DBPCT (N=200) found possible efficacy in the treatment of alcohol dependence.[4] Previous studies had shown that it reduced alcohol consumption in heavy-drinking smokers.[5][6]


Side effectsEdit

Common side effects (occurring in ≥1% of patients) include: appetite changes, dry mouth, taste disturbances and headache, drowsiness, dizziness, sleep disorders and abnormal dreams.[7] Less common side effects include (occurring in fewer than 1% of patients): thirst, weight gain, canker sores, gum pain, chest pain, high blood pressure, high heart rate, atrial fibrilation, depression, hallucinations, delusions, palpitations, suicidal thoughts, etc.[7]

Mechanism of actionEdit

It is a nicotinic agent that serves as a partial agonist at the α4β2, α3β4, α3β2 and α6 subunits, whereas it serves as a full agonist at α7.[8]

External linksEdit

Reference listEdit

  1. Hays, JT; Ebbert, JO (November 2008). "Varenicline for tobacco dependence.". The New England Journal of Medicine 359 (19): 2018–24. PMC 2959114. PMID 18987369. doi:10.1056/NEJMct0800146. 
  2. Williams, JM; Steinberg, MB; Steinberg, ML; Gandhi, KK; Ulpe, R; Foulds, J (August 2011). "Varenicline for tobacco dependence: panacea or plight?". Expert Opinion on Pharmacotherapy 12 (11): 1799–812. PMC 3132819. PMID 21644843. doi:10.1517/14656566.2011.587121. 
  3. Mohanasundaram, UM; Chitkara, R; Krishna, G (2008). "Smoking cessation therapy with varenicline.". International Journal of Chronic Obstructive Pulmonary Disease 3 (2): 239–51. PMC 2629973. PMID 18686733. doi:10.2147/COPD.S1848. 
  4. Litten, RZ; Ryan, ML; Fertig, JB; Falk, DE; Johnson, B; Dunn, KE; Green, AI; Pettinati, HM; Ciraulo, DA; Sarid-Segal, O; Kampman, K; Brunette, MF; Strain, EC; Tiouririne, NA; Ransom, J; Scott, C; Stout, R; NCIG (National Institute on Alcohol Abuse and Alcoholism Clinical Investigations Group) Study (July-August 2013). "A double-blind, placebo-controlled trial assessing the efficacy of varenicline tartrate for alcohol dependence.". Journal of Addiction Medicine 7 (4): 277–86. PMC 3914416. PMID 23728065. doi:10.1097/ADM.0b013e31829623f4.  Check date values in: |date= (help)
  5. McKee, SA; Harrison, EL; O'Malley, SS; Krishnan-Sarin, S; Shi, J; Tetrault, JM; Picciotto, MR; Petrakis, IL; Estevez, N; Balchunas, E (July 2009). "Varenicline reduces alcohol self-administration in heavy-drinking smokers.". Biological Psychiatry 66 (2): 185–90. PMC 2863311. PMID 19249750. doi:10.1016/j.biopsych.2009.01.029. 
  6. Mitchell, JM; Teague, CH; Kayser, AS; Bartlett, SE; Fields, HL (October 2012). "Varenicline decreases alcohol consumption in heavy-drinking smokers.". Psychopharmacology 223 (3): 299–306. PMC 3438402. PMID 22547331. doi:10.1007/s00213-012-2717-x. 
  7. 7.0 7.1 Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. p. 327. ISBN 9780857110848. 
  8. Mihalak, KB; Carroll, FI; Luetje, CW (September 2006). "Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors.". Molecular Pharmacology 70 (3): 801–5. PMID 16766716. doi:10.1124/mol.106.025130. 

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