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

Details

Stereochemistry RACEMIC
Molecular Formula C13H18ClNO
Molecular Weight 239.7415
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPROPION

SMILES

CC(C(=O)c1cccc(c1)Cl)NC(C)(C)C

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 239.7415
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB01156 | http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm103318.htm

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
WELLBUTRIN

Approved Use

INDICATIONS & USAGE Major Depressive Disorder:Bupropion hydrochloride extended-release tablets (XL) are indicated for the treatment of major depressive disorder. The efficacy of bupropion in the treatment of a major depressive episode was established in two 4-week controlled trials of inpatients and in one 6-week controlled trial of outpatients whose diagnoses corresponded most closely to the Major Depression category of the APA Diagnostic and Statistical Manual (DSM) (seeCLINICAL TRIALS). A major depressive episode (DSM-IV) implies the presence of 1) depressed mood or 2) loss of interest or pleasure; in addition, at least 5 of the following symptoms have been present during the same 2-week period and represent a change from previous functioning: depressed mood, markedly diminished interest or pleasure in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt, or suicidal ideation. The efficacy of bupropion in maintaining an antidepressant response for up to 44 weeks following 8 weeks of acute treatment was demonstrated in a placebo-controlled trial with the sustained-release formulation of bupropion (seeCLINICAL TRIALS). Nevertheless, the physician who elects to use bupropion hydrochloride extended-release tablets (XL) for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient. Seasonal Affective Disorder:Bupropion hydrochloride extended-release tablets (XL) are indicated for the prevention of seasonal major depressive episodes in patients with a diagnosis of seasonal affective disorder. The efficacy of bupropion hydrochloride extended-release tablets (XL) for the prevention of seasonal major depressive episodes was established in 3 controlled trials of adult outpatients with a history of major depressive disorder with an autumn-winter seasonal pattern as defined by Diagnostic and Statistical Manual of Mental Disorders, 4th edition (DSM-IV) criteria (seeCLINICAL TRIALS). Seasonal affective disorder is characterized by recurrent major depressive episodes, most commonly occurring during the autumn and/or winter months. Episodes may last up to 6 months in duration, typically beginning in the autumn and remitting in the springtime. Although patients with seasonal affective disorder may have depressive episodes during other times of the year, the diagnosis of seasonal affective disorder requires that the number of seasonal episodes substantially outnumber the number of non-seasonal episodes during the individual's lifetime.

Launch Date

5.04748802E11
Primary
ZYBAN

Approved Use

Zyban is indicated as an aid to smoking cessation treatment.

Launch Date

5.04748802E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
134 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
93 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
136 ng/mL
150 mg 2 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
91 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
688 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
469 ng × h/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10 h
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
21 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
16%
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
unhealthy, adult
n = 214
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 214
Sources:
Other AEs: Seizures...
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Disc. AE: Neuropsychiatric symptoms, Gastrointestinal disturbance...
Other AEs: Neuropsychiatric symptoms...
AEs leading to
discontinuation/dose reduction:
Neuropsychiatric symptoms (3%)
Gastrointestinal disturbance (2.1%)
Neurological disorder NOS (1.7%)
Skin and subcutaneous tissue disorders (1.4%)
Other AEs:
Neuropsychiatric symptoms
Sources:
AEs

AEs

AESignificanceDosePopulation
Seizures 2.8%
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
unhealthy, adult
n = 214
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 214
Sources:
Neuropsychiatric symptoms
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Skin and subcutaneous tissue disorders 1.4%
Disc. AE
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Neurological disorder NOS 1.7%
Disc. AE
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Gastrointestinal disturbance 2.1%
Disc. AE
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Neuropsychiatric symptoms 3%
Disc. AE
600 mg 1 times / day multiple, oral (max)
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
n = 2400
Health Status: unhealthy
Condition: depression
Age Group: adult
Sex: unknown
Population Size: 2400
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive
yes [IC50 9.3 uM]
yes
yes (co-administration study)
Comment: from FDA label https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021515s040lbl.pdf: coadministration with desipramine increased the Cmax of desipramine by 2-fold, and AUC by 5-fold
Page: 90.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
likely
minor
minor
minor
minor
minor
yes
yes (co-administration study)
Comment: from FDA label https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021515s040lbl.pdf: coadministration with ticlopidine increased buproprion Cmax 38% and AUC by 85%
Page: 10.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
A placebo-controlled comparison of the antidepressant efficacy and effects on sexual functioning of sustained-release bupropion and sertraline.
1999 Apr
Phenelzine-induced sexual dysfunction treated with sildenafil.
1999 Apr-Jun
Sexual dysfunction associated with the treatment of depression: a placebo-controlled comparison of bupropion sustained release and sertraline treatment.
1999 Dec
Development of depression during placebo-controlled trials of bupropion for smoking cessation: case reports.
1999 Jul
Bupropion mimics a transient ischemic attack.
1999 Mar
Antidepressants upregulate messenger RNA levels of the neuroprotective enzyme superoxide dismutase (SOD1).
2000 Jan
Visual and auditory hallucinations with the association of bupropion and valproate.
2000 Mar
Algorithm for the treatment of chronic depression.
2001
Nortriptyline toxicity secondary to interaction with bupropion sustained-release.
2001
Incidence of sexual dysfunction associated with antidepressant agents: a prospective multicenter study of 1022 outpatients. Spanish Working Group for the Study of Psychotropic-Related Sexual Dysfunction.
2001
Bupropion sustained release for bereavement: results of an open trial.
2001 Apr
Modification of norepinephrine and serotonin, but not dopamine, neuron firing by sustained bupropion treatment.
2001 Apr
Bupropion overdose in an adolescent.
2001 Apr
Effects of bupropion sustained-release on sexual functioning and nocturnal erections in healthy men.
2001 Feb
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
2001 Feb
Smoking cessation. Pulling out the stops.
2001 Feb 15
Bupropion for smokers. Drug is almost identical in structure to diethylpropion, a controlled drug.
2001 Feb 17
Antismoking drug comes under scrutiny after deaths.
2001 Feb 24
Treatment of attention-deficit hyperactivity disorder.
2001 Jan
Cytochrome P-450 2B6 is responsible for interindividual variability of propofol hydroxylation by human liver microsomes.
2001 Jan
A 25-year-old woman with bipolar disorder.
2001 Jan 24-31
Smoking cessation: integrating recent advances into clinical practice.
2001 Jul
Response in relation to baseline anxiety levels in major depressive disorder treated with bupropion sustained release or sertraline.
2001 Jul
The Stanley Foundation Bipolar Network. I. Rationale and methods.
2001 Jun
Depression and anxiety disorders.
2001 Jun
Bupropion SR as an aid to smoking cessation in smokers treated previously with bupropion: a randomized placebo-controlled study.
2001 Jun
Bupropion-induced erythema multiforme.
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
Substitution of an SSRI with bupropion sustained release following SSRI-induced sexual dysfunction.
2001 Mar
Titer-dependent antagonism of cocaine following active immunization in rhesus monkeys.
2001 Mar
Type II error and antidepressants.
2001 May
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
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.
2001 May
Smoking cessation. The key to treating older smokers? Don't quit helping.
2001 May
Use of bupropion SR in a pharmacist-managed outpatient smoking-cessation program.
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
Pharmacological aids for smoking cessation.
2001 Spring
Pharmacokinetic interactions between cyclosporine and bupropion or methylphenidate.
2001 Summer
Patents

Sample Use Guides

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
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 Fri Jun 25 22:08:37 UTC 2021
Edited
by admin
on Fri Jun 25 22:08:37 UTC 2021
Record UNII
01ZG3TPX31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPROPION
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-758686
Code 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 Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
LIVERTOX 128
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NDF-RT N0000009282
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NDF-RT N0000000114
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
WHO-VATC QN06AX12
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
WHO-ATC A08AA62
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NDF-RT N0000009456
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NDF-RT N0000000102
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NCI_THESAURUS C265
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
NDF-RT N0000180855
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
Code System Code Type Description
INN
3562
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
MERCK INDEX
M2773
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB01156
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
NCI_THESAURUS
C62012
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
WIKIPEDIA
BUPROPION
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
LACTMED
Bupropion
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
RXCUI
42347
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY RxNorm
EPA CompTox
34911-55-2
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
DRUG CENTRAL
435
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
CAS
34841-39-9
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
SUPERSEDED
FDA UNII
01ZG3TPX31
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
MESH
D016642
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
CAS
34911-55-2
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL894
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
PUBCHEM
444
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
EVMPD
SUB05413MIG
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
HSDB
6988
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
IUPHAR
7135
Created by admin on Fri Jun 25 22:08:38 UTC 2021 , Edited by admin on Fri Jun 25 22:08:38 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
FECAL; URINE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
Strong Inhibitors(2) 5-fold increase in AUC or > 80% decrease in CL
MAJOR
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
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
Tmax PHARMACOKINETIC FASTED STATE

ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

FED CONDITION