The Bupropion reference article from the English Wikipedia on 24-Apr-2004 (provided by Fixed Reference: snapshots of Wikipedia from wikipedia.org)

Bupropion

Bupropion (amfebutamone) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or SSRIs. It is similar in structure to the stimulant cathinone, and to phenethylamines in general. The half-life of bupropion in the body is anywhere from 10 - 21 hours, and is eliminated mainly through urination.

Buopropion was first synthesized by Burroughs Research in 1966, and patented by Burroughs-Wellcomme in 1974. It was approved by the FDA in 1985 and marketed under the name "Wellbutrin" as an antidepressant, but clinical trials indicated that incidence of seizure was two to four times greater than other antidepressants and the drug was quickly pulled from the market. Glaxo, realizing that seizure risk was a function of dosage, then developed and marketed a sustained-release (SR) version of Wellbutrin which, when ingested, releases bupropion HCl at a constant, gradual rate into the body. Because of this altered mechanism of delivery, incidence of seizure with Wellbutrin-SR is comparable to, and in some cases, lower than that of other antidepressants.

In 1997, bupropion HCl was approved by the FDA for use as a smoking cessation aid. Because the name "Wellbutrin" was still associated with high seizure risk, the drug was subsequently marketed by Glaxo under the name Zyban.

Although the exact mode of action is unknown, it is suspected that bupropion inhibits the reuptake of dopamine, serotonin, and norepinephrine, which may contribute to its antidepressant activity. Note that MAO inhibition also fails to explain its properties.

Common side effects include anxiety, loss of appetite (SR form only), agitation, dizziness, headache, excessive sweating, increased risk of seizure, and insomnia.

Note that sexual side effects normally accompanying SSRI's do not accompany Wellbutrin. Interestingly, patients commonly report increased libido, perhaps evidence of its dopaminergic properties.

Data

The following applies to the hydrochloride salt:

International Nonproprietary Name>INN:	bupropion hydrochloride
IUPAC name:	(±)-1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride
CAS number:	31677-93-7
Chemical formula:	C13H18ClNO·HCl
Molecular weight:	amu

• White, crystalline powder
• Highly soluble in water

External links

• Wellbutrin Pharmacology, Pharmacokinetics, Studies, Metabolism - Bupropion - RxList Monographs
• NAMI Wellbutrin

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