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Details

Stereochemistry RACEMIC
Molecular Formula C13H18ClNO.C4H4O4
Molecular Weight 355.813
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BUPROPION MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(NC(C)(C)C)C(=O)C1=CC=CC(Cl)=C1

InChI

InChIKey=NJJFBMJGOYCQCX-BTJKTKAUSA-N
InChI=1S/C13H18ClNO.C4H4O4/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;5-3(6)1-2-4(7)8/h5-9,15H,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C13H18ClNO
Molecular Weight 239.741
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Bupropion, an antidepressant of the aminoketone class and a non-nicotine aid to smoking cessation, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine, serotonin, and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behavior tasks, and, at high doses, induction of mild stereotyped behavior. Bupropion is marketed as Wellbutrin, Zyban, and generics. Bupropion is indicated for the treatment of major depressive disorder (MDD). WELLBUTRIN, WELLBUTRIN SR, and WELLBUTRIN XL are not approved for smoking cessation treatment, but bupropion under the name ZYBAN is approved for this use.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Algorithm for the treatment of chronic depression.
2001
Nortriptyline toxicity secondary to interaction with bupropion sustained-release.
2001
Bupropion overdose: a potential problem with the new 'miracle' anti-smoking drug.
2001 Apr
[Bupropion: a new hope for smokers willing to quit].
2001 Apr
Effects of sustained-release bupropion and supportive group therapy on cigarette consumption in patients with schizophrenia.
2001 Apr
Effects of bupropion SR on anterior paralimbic function during waking and REM sleep in depression: preliminary findings using.
2001 Apr 10
Bupropion hydrochloride: the development of a chiral separation using an ovomucoid column.
2001 Apr 13
Antidepressants in the treatment of patients with COPD: possible associations between smoking cigarettes, COPD and depression.
2001 Aug
Use of dopamine-beta-hydroxylase-deficient mice to determine the role of norepinephrine in the mechanism of action of antidepressant drugs.
2001 Aug
Evaluation of the contribution of cytochrome P450 3A4 to human liver microsomal bupropion hydroxylation.
2001 Aug
Techniques for smoking cessation: what really works?
2001 Feb
[Zyban in smoking cessation].
2001 Feb 10
[Bupropion; an effective new aid for smoking cessation].
2001 Feb 10
[Risk of convulsions due to the use of bupropion as an aid for smoking cessation].
2001 Feb 10
Smoking cessation. Pulling out the stops.
2001 Feb 15
Bupropion for smokers. Bupropion may not be as good as editorial implies.
2001 Feb 17
Bupropion for smokers. Where are practices supposed to find money for bupropion?
2001 Feb 17
Bupropion for smokers. New products for smoking cessation maintain profile of smoking cessation services.
2001 Feb 17
Antismoking drug comes under scrutiny after deaths.
2001 Feb 24
Treatment of attention-deficit hyperactivity disorder.
2001 Jan
[Recent advances in research on nicotine dependence and reward mechanism].
2001 Jan
A 25-year-old woman with bipolar disorder.
2001 Jan 24-31
The pharmacology underlying pharmacotherapy for tobacco dependence: a focus on bupropion.
2001 Jan-Feb
Single-dose pharmacokinetics of bupropion in adolescents: effects of smoking status and gender.
2001 Jul
Effects of cocaine prior to and during bupropion maintenance in cocaine-abusing volunteers.
2001 Jul 1
Bupropion manic induction during euthymia, but not during depression.
2001 Jun
Seizure during combination of trimipramine and bupropion.
2001 Jun
The Stanley Foundation Bipolar Network. I. Rationale and methods.
2001 Jun
Depression and anxiety disorders.
2001 Jun
Variations in treatment benefits influence smoking cessation: results of a randomised controlled trial.
2001 Jun
Bupropion sustained-release for the treatment of dysthymic disorder: an open-label study.
2001 Jun
Erythema multiforme associated with bupropion use.
2001 Jun 25
Tobacco-use cessation programs and policies at the University of Manitoba's faculty of dentistry.
2001 Mar
Titer-dependent antagonism of cocaine following active immunization in rhesus monkeys.
2001 Mar
Smoking cessation in the hospitalized patient using the transtheoretical model of behavior change.
2001 Mar-Apr
Late-term smoking cessation despite initial failure: an evaluation of bupropion sustained release, nicotine patch, combination therapy, and placebo.
2001 May
Smoking cessation. The key to treating older smokers? Don't quit helping.
2001 May
The use of bupropion in the treatment of restlessness after a traumatic brain injury.
2001 May
Use of bupropion SR in a pharmacist-managed outpatient smoking-cessation program.
2001 May
Bupropion for smoking cessation : predictors of successful outcome.
2001 May
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines.
2001 May
Identification and treatment of depression in a cohort of patients maintained on chronic peritoneal dialysis.
2001 May
Seizures after buproprion overdose.
2001 May 19
Smoking cessation in patients with chronic obstructive pulmonary disease: a double-blind, placebo-controlled, randomised trial.
2001 May 19
Place of bupropion in smoking-cessation therapy.
2001 May 19
[Nicotine-free pill. Easy smoking cessation].
2001 May 3
Bupropion and serum sickness-like reaction.
2001 May 7
Bupropion sustained release (SR) for the treatment of hypoactive sexual desire disorder (HSDD) in nondepressed women.
2001 May-Jun
Pharmacological aids for smoking cessation.
2001 Spring
Pharmacokinetic interactions between cyclosporine and bupropion or methylphenidate.
2001 Summer
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult dose is 300 mg/day, given 3 times daily. Dosing should begin at 200 mg/day, given as 100 mg twice daily. Based on clinical response, this dose may be increased to 300 mg/day, given as 100 mg 3 times daily, no sooner than 3 days after beginning therapy.
Route of Administration: Oral
In Vitro Use Guide
Bupropion (10 uM) significantly decreased nicotine-evoked [(3)H]dopamine release by approximately 50% in rat striatal synaptosomes and slices.
Substance Class Chemical
Created
by admin
on Tue Oct 22 12:36:40 UTC 2019
Edited
by admin
on Tue Oct 22 12:36:40 UTC 2019
Record UNII
26NV8NXO4A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPROPION MALEATE
Common Name English
1-PROPANONE, 1-(3-CHLOROPHENYL)-2-((1,1-DIMETHYLETHYL)AMINO)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
1013636-49-1
Created by admin on Tue Oct 22 12:36:40 UTC 2019 , Edited by admin on Tue Oct 22 12:36:40 UTC 2019
NON-SPECIFIC STOICHIOMETRY
CAS
93109-98-9
Created by admin on Tue Oct 22 12:36:40 UTC 2019 , Edited by admin on Tue Oct 22 12:36:40 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE