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Bupropion

Bupropion (Budeprion, Wellbutrin, Zyban, Aplenzin), is a non-traditional antidepressant since it is primarily a NDRI which has weak affinity for serotonin. It is related to phenethylamines, an aminokeytone and a substituted cathinone, but shares little in effect with other substituted cathinones. It is sometimes used by itself or in conjunction with SSRI's for treatment of depression. It is also used in non-nicotine smoking cessation. Higher doses lower the seizure threshold. Some recreational users who insufflate bupropion report it produces a stimulant-like effect, however nasal insufflation of Bupropion has been associated with seizures.

Contents




[top]Introduction to Bupropion

Bupropion (Wellbutrin, Zyban), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely resembles that of diethylpropion; it is related to phenylethylamines and is a substituted cathinone.

Also known as: Amfebutamone, Amfebutamon, (+-)-Bupropion, amfebutamonum, Amfebutamona, Wellbatrin, Bupropion hydrocloride, CHEBI:3219, Elont

Bupropion hydrochloride powder is white, crystalline, and highly soluble in water. It has a bitter taste and produces the sensation of local anesthesia on the oral mucosa.[1]


[top]Using Bupropion

[top]Ways of administration


WELLBUTRIN XL Tablets are supplied for oral administration as 150-mg and 300-mg, creamy-white to pale yellow extended-release tablets. Each tablet contains the labeled amount of bupropion hydrochloride and the inactive ingredients: ethylcellulose aqueous dispersion (NF), glyceryl behenate, methacrylic acid copolymer dispersion (NF), polyvinyl alcohol, polyethylene glycol, povidone, silicon dioxide, and triethyl citrate. The tablets are printed with edible black ink.

The insoluble shell of the extended-release tablet may remain intact during gastrointestinal transit and is eliminated in the feces.[1]

[top]Effects of Bupropion

Wellbutrin SR is the earlier 1996 FDA-approved sustained-release formulation of Bupropion. Intended to be taken twice a day it comes in blue-coated 100 mg, purple-coated 150 mg and pink-coated 200 mg pills.

[top]Combinations with Bupropion

[top]Different Uses for Bupropion

[top]Depression

[top]Non-Nicotine Smoking Cessation

[top]ADD/ADHD



[top]Pharmacology of Bupropion

LD50 (mg/kg) :
Mice : 575 oral ; 230 intraperitoneal
Rat : 600 oral ; 210 intraperitoneal


[top]Chemistry of Bupropion

Title compound:Bupropion
Systematic (IUPAC) name:1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone
Synonyms:()-2-(tert-butylamino)-3'-chloropropiophenone, m-chloro-[alpha]-(tert-butylamino)propiophenone, amphebutamone ; Budeprion, Wellbutrin, Zyban (hydrochloride) ; Aplenzin (hydrobromide)
Molecular Formula:C13H18ClNO
Molar mass: 239.74 g/mol ; 270.20 g/mol (hydrochloride) ; 320.66 g/mol (hydrobromide)
CAS Registry Number:34841-39-9 ; 31667-93-7 (hydrochloride) ; 905818-69-1 (hydrobromide)
Melting Point:233-234C (hydrochloride)
Boiling Point: 52C @ 0.005 mmHg
Flash Point:no data
Solubility:Soluble in methanol, ethanol, acetone, ether, benzene ; Water 312 mg/mL, alcohol 193 mg/mL, 0.1M HCl 333 mg/mL (hydrochloride) ; Soluble in water (hydrobromide)
Additionnal data:pKa 7.9
Notes: Freebase very hygroscopic, prone to decomposition. Freebase aspect : pale yellow oil. Hydrochloride : crystals from isopropanol and absolute ethanol. Hydrobromide : white, almost white crystalline powder
[2]
MSDS
Downloadable .pdf
Attachment 30935


[top]The dangers of Bupropion



[top]Producing Bupropion

Bupropion is commercially produced following the pathway given below (from [1]) :


[top]Forms of Bupropion



[top]Legal status of Bupropion

[top]United Nations

[top]USA

[top]EU

[top]Other Countries



[top]History of Bupropion



Bupropion was invented by Nariman Mehta of Burroughs Wellcome (now GlaxoSmithKline) in 1969, and the US patent for it was granted in 1974. It was approved by the United States Food and Drug Administration (FDA) as an antidepressant on December 30, 1985, and marketed under the name Wellbutrin. However, a significant incidence of seizures at the originally recommended dosage (400600 mg) caused the withdrawal of the drug in 1986. Subsequently, the risk of seizures was found to be highly dose-dependent, and bupropion was re-introduced to the market in 1989 with a maximum recommended dose of 450 mg/day.

In 1996, the FDA approved a sustained-release formulation of bupropion called Wellbutrin SR, intended to be taken twice a day (as compared with three times a day for immediate-release Wellbutrin). In 2003, the FDA approved another sustained-release formulation called Wellbutrin XL, intended for once-daily dosing. Wellbutrin SR and XL are available in generic form in the United States, while in Canada, only the SR formulation is available in generic form. In 1997, bupropion was approved by the FDA for use as a smoking cessation aid under the name Zyban. In 2006, Wellbutrin XL was similarly approved as a treatment for seasonal affective disorder.

In 2012, the U.S. Justice Department announced that GlaxoSmithKline had agreed to plead guilty and pay a $3-billion fine, in part for promoting the unapproved use of Wellbutrin for weight loss and sexual dysfunction.

In April 2008, the FDA approved a formulation of bupropion as a hydrobromide salt instead of a hydrochloride salt, to be sold under the name Aplenzin by Sanofi-Aventis.

On October 11, 2007, two providers of consumer information on nutritional products and supplements, ConsumerLab and The People's Pharmacy, released the results of comparative tests of different brands of bupropion. The People's Pharmacy received multiple reports of increased side effects and decreased efficacy of generic bupropion, which prompted it to ask the online ConsumerLab blog to test the products in question. The tests showed that "one of a few generic versions of Wellbutrin XL 300 mg, sold as Budeprion XL 300 mg, didn't perform the same as the brand-name pill in the lab." The FDA investigated these complaints and concluded that the Budeprion XL is equivalent to Wellbutrin XL in regard to bioavailability of bupropion and its main active metabolite hydroxybupropion. The FDA also said that coincidental natural mood variation is the most likely explanation for the apparent worsening of depression after the switch from Wellbutrin XL to Budeprion XL. On October 3, 2012, however, the FDA reversed this opinion, announcing that "Budeprion XL 300 mg fails to demonstrate therapeutic equivalence to Wellbutrin XL 300 mg." The FDA did not test the bioequivalence of any of the other generic versions of Wellbutrin XL 300 mg, but requested that the four manufacturers submit data on this question to the FDA by May, 2013.

In France, marketing authorization was granted for Zyban on August 3, 2001, with a maximum daily dose of 300 mg; only sustained-release bupropion is available, and only as a smoking cessation aid. Bupropion was granted a licence for use in adults with major depression in the Netherlands in early 2007, with GlaxoSmithKline expecting subsequent approval in other European countries.


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[top]References

[REFLIST][1] Synthesis of Essential Drugs, 1st edition, Ruben Vardanyan & Victor Hruby, Elsevier
[2]Merck Index, fifteenth edition[/REFLIST


Created by Nanashi, 08-08-2011 at 02:29
Last edited by John_bob, 19-04-2014 at 13:19
Last comment by John_bob on 16-03-2014 at 11:27
6 Comments, 38,862 Views

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