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Bupropion (Molecule of the Month for April 2016)

Wellbutrin, Zyban, Budeprion, Buproban



Bupropion is as an antidepressant and as a smoking cessation drug. In 2006 it was the fourth most prescribed antidepressant on the U.S. retail market with over 21M prescriptions. Bupropion was first synthesized by Burroughs Research in 1966, and patented by Burroughs-Wellcome in 1974. It was approved by the Food and Drug Administration (FDA) as an antidepressant in 1984 and marketed under the name Wellbutrin.

However, a significant incidence of seizures at the originally recommended dosage (400-600 mg) caused in 1986 the removal of the drug from the market. It was shown that the risk of seizures increases from 0.1% at 100-300 mg/day to 0.3-0.4% at 450 mg/day to 2% at 600 mg/day. Reflecting this experience, bupropion was re-introduced to the market in 1989 with the maximum dose of 450 mg/day.

In 1997, bupropion was approved by the FDA for use as a smoking cessation aid under the name Zyban. In the UK, bupropion was approved in 2000 as a smoking cessation aid, and it is not approved for the treatment of depression. Bupropion's main use is for smoking cessation. It reduces the severity of nicotine cravings and addiction/withdrawal symptoms. Urge to smoke was a problem for 27% of subjects receiving bupropion vs 56% receiving placebo at the end of a 7-week treatment. 21% of the bupropion group reported mood swings vs 32% of the placebo group in the same study. Bupropion treatment course lasts for seven to twelve weeks, with the patient halting the use of tobacco around ten days into the course. The efficacy of bupropion is similar to that of nicotine replacement therapy. Bupropion approximately doubles the chance of quitting smoking successfully after 3 months. 1 year after the treatment the odds of sustaining smoking cessation are still 1.5 higher in the bupropion group than in the placebo group. In a direct comparison, recently approved varenicline (Chantix) showed superior efficacy.

Formal Chemical Name (IUPAC)
()-1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone

References

http://en.wikipedia.org/wiki/Bupropion

Picture of Bupropion 3D model

click on the picture of  Bupropion above to interact
with the 3D model of the
Bupropion structure
(this will open a new browser window)

Picture of Bupropion

C13 H18 Cl N O



Update by Karl Harrison
(Molecule of the Month for April 2016 )

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