U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

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

SHOW SMILES / InChI
Structure of BUPROPION

SMILES

CC(NC(C)(C)C)C(=O)C1=CC=CC(Cl)=C1

InChI

InChIKey=SNPPWIUOZRMYNY-UHFFFAOYSA-N
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3

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 ( + / - )

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
Nortriptyline toxicity secondary to interaction with bupropion sustained-release.
2001
Strategies for the treatment of antidepressant-related sexual dysfunction.
2001
The effects of antidepressants on sexual functioning in depressed patients: a review.
2001
Bupropion sustained release for bereavement: results of an open trial.
2001 Apr
[Pharmacologic therapy for smoking cessation].
2001 Apr
Bupropion overdose in an adolescent.
2001 Apr
Does pretreatment anxiety predict response to either bupropion SR or sertraline?
2001 Apr
Effects of sustained-release bupropion and supportive group therapy on cigarette consumption in patients with schizophrenia.
2001 Apr
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
[Zyban and medical ethics].
2001 Feb 28
[Zyban in smoking cessation--where is medical ethics?].
2001 Feb 28
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
Treating nicotine dependence.
2001 Jan-Feb
Response in relation to baseline anxiety levels in major depressive disorder treated with bupropion sustained release or sertraline.
2001 Jul
Bupropion manic induction during euthymia, but not during depression.
2001 Jun
Seizure during combination of trimipramine and bupropion.
2001 Jun
Bupropion SR as an aid to smoking cessation in smokers treated previously with bupropion: a randomized placebo-controlled study.
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
A practical guide to tobacco cessation in dental offices.
2001 Mar
Tobacco-use cessation programs and policies at the University of Manitoba's faculty of dentistry.
2001 Mar
Bupropion sustained release in adolescents with comorbid attention-deficit/hyperactivity disorder and depression.
2001 Mar
Smoking cessation in the hospitalized patient using the transtheoretical model of behavior change.
2001 Mar-Apr
Relationship between drug exposure and the efficacy and safety of bupropion sustained release for smoking cessation.
2001 May
Bupropion SR worsens mood during marijuana withdrawal in humans.
2001 May
Late-term smoking cessation despite initial failure: an evaluation of bupropion sustained release, nicotine patch, combination therapy, and placebo.
2001 May
Ondansetron rather than metoclopramide for bupropion-induced nausea.
2001 May
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.
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
Sustained-release bupropion for selective serotonin reuptake inhibitor-induced sexual dysfunction: a randomized, double-blind, placebo-controlled, parallel-group study.
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
[Nicotine-free pill. Easy smoking cessation].
2001 May 3
Newly available treatments for nicotine addiction. Smokers wanting help with stopping now have effective treatment options.
2001 May 5
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
Pharmacologic treatments for the nicotine dependent smoker.
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 00:23:19 UTC 2019
Edited
by admin
on Tue Oct 22 00:23:19 UTC 2019
Record UNII
01ZG3TPX31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPROPION
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
BUPROPION [MI]
Common Name English
BUPROPION SLOW RELEASE
Common Name English
AMFEBUTAMONE
Common Name English
1-PROPANONE, 1-(3-CHLOROPHENYL)-2-((1,1-DIMETHYLETHYL)AMINO)-(+/-)-
Systematic Name English
BUPROPION [INN]
Common Name English
(+/-)-2-(TERT-BUTYLAMINO)-3'-CHLOROPROPIOPHENONE
Systematic Name English
BUPROPION COMPONENT OF CONTRAVE
Brand Name English
BUPROPION [WHO-DD]
Common Name English
BUPROPION [VANDF]
Common Name English
BUPROPION EXTENDED RELEASE
Common Name English
BUPROPION [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N06AX12
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
LIVERTOX 128
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NDF-RT N0000009282
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NDF-RT N0000000114
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
WHO-VATC QN06AX12
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
WHO-ATC A08AA62
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NDF-RT N0000009456
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NDF-RT N0000000102
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NCI_THESAURUS C265
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
NDF-RT N0000180855
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
Code System Code Type Description
INN
3562
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
MERCK INDEX
M2773
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY Merck Index
LactMed
34911-55-2
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
NCI_THESAURUS
C62012
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
WIKIPEDIA
BUPROPION
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
RXCUI
42347
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY RxNorm
EPA CompTox
34911-55-2
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
CAS
34841-39-9
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
SUPERSEDED
MESH
D016642
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
CAS
34911-55-2
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL894
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
PUBCHEM
444
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
EVMPD
SUB05413MIG
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
HSDB
34911-55-2
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
IUPHAR
7135
Created by admin on Tue Oct 22 00:23:19 UTC 2019 , Edited by admin on Tue Oct 22 00:23:19 UTC 2019
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
Strong Inhibitors(2) 5-fold increase in AUC or > 80% decrease in CL
MAJOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC