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

Details

Stereochemistry RACEMIC
Molecular Formula C13H18ClNO.ClH
Molecular Weight 276.202
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPROPION HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C13H18ClNO
Molecular Weight 239.741
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Sexual dysfunction associated with the treatment of depression: a placebo-controlled comparison of bupropion sustained release and sertraline treatment.
1999 Dec
Bupropion-induced isolated impairment of sensory trigeminal nerve function.
2000 Mar
Bupropion treatment-related sexual side effects: a case report.
2000 Mar
Visual and auditory hallucinations with the association of bupropion and valproate.
2000 Mar
Seizure after guanfacine plus bupropion: correction.
2000 Nov
Algorithm for the treatment of chronic depression.
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
Modification of norepinephrine and serotonin, but not dopamine, neuron firing by sustained bupropion treatment.
2001 Apr
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
Bupropion hydrochloride: the development of a chiral separation using an ovomucoid column.
2001 Apr 13
Techniques for smoking cessation: what really works?
2001 Feb
A free smoking intervention clinic initiated by medical students.
2001 Feb
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
2001 Feb
A controlled clinical trial of bupropion for attention deficit hyperactivity disorder in adults.
2001 Feb
[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. Where are practices supposed to find money for bupropion?
2001 Feb 17
Bupropion for smokers. Drug is almost identical in structure to diethylpropion, a controlled drug.
2001 Feb 17
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
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
The Stanley Foundation Bipolar Network. I. Rationale and methods.
2001 Jun
Bupropion-induced erythema multiforme.
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
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
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
Smoking cessation in patients with chronic obstructive pulmonary disease: a double-blind, placebo-controlled, randomised trial.
2001 May 19
Bupropion sustained release (SR) for the treatment of hypoactive sexual desire disorder (HSDD) in nondepressed women.
2001 May-Jun
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 Dec 16 20:50:49 UTC 2022
Edited
by admin
on Fri Dec 16 20:50:49 UTC 2022
Record UNII
ZG7E5POY8O
Record Status Validated (UNII)
Record Version
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Name Type Language
BUPROPION HYDROCHLORIDE
HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
BUPROPION HYDROCHLORIDE [JAN]
Common Name English
BUPROPION HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BUPROPION HYDROCHLORIDE COMPONENT OF AUVELITY
Common Name English
BUPROPION HYDROCHLORIDE [MI]
Common Name English
BUPROPION HYDROCHLORIDE [USP-RS]
Common Name English
NSC-315851
Code English
BUPROPION HYDROCHLORIDE [USP IMPURITY]
Common Name English
MYSIMBA
Brand Name English
BUPROPION HYDROCHLORIDE COMPONENT OF CONTRAVE
Brand Name English
BW-323
Code English
BUPROPION HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
BUPROPION HYDROCHLORIDE [VANDF]
Common Name English
1-PROPANONE, 1-(3-CHLOROPHENYL)-2-((1,1-DIMETHYLETHYL)AMINO)-, HYDROCHLORIDE, (±)-
Systematic Name English
Bupropion hydrochloride [WHO-DD]
Common Name English
BUPROPION HYDROCHLORIDE [USAN]
Common Name English
BUPROPION HCL
Common Name English
AUVELITY COMPONENT BUPROPION HYDROCHLORIDE
Common Name English
BUPROPION HYDROCHLORIDE [MART.]
Common Name English
AMFEBUTAMONE HYDROCHLORIDE
Common Name English
BUPROPION HYDROCHLORIDE [HSDB]
Common Name English
BW323
Code English
CONTRAVE COMPONENT BUPROPION HYDROCHLORIDE
Brand Name English
(±)-2-(TERT-BUTYLAMINO)-3'-CHLOROPROPIOPHENONE HYDROCHLORIDE
Systematic Name English
WELLBUTRIN
Brand Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS MYSIMBA (AUTHORIZED: OVERWEIGHT)
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
EMA ASSESSMENT REPORTS MYSIMBA (AUTHORIZED: OBESITY)
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
NCI_THESAURUS C265
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
Code System Code Type Description
MERCK INDEX
M2773
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY Merck Index
PUBCHEM
62884
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
PRIMARY
FDA UNII
ZG7E5POY8O
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
DRUG BANK
DBSALT000199
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
NSC
315851
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
PRIMARY
CAS
31677-93-7
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
DAILYMED
ZG7E5POY8O
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
RS_ITEM_NUM
1078733
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
PRIMARY
EVMPD
SUB00432MIG
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
RXCUI
203204
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
PRIMARY RxNorm
EPA CompTox
DTXSID6044561
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
ECHA (EC/EINECS)
250-759-9
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
ChEMBL
CHEMBL894
Created by admin on Fri Dec 16 20:50:49 UTC 2022 , Edited by admin on Fri Dec 16 20:50:49 UTC 2022
PRIMARY
NCI_THESAURUS
C1317
Created by admin on Fri Dec 16 20:50:50 UTC 2022 , Edited by admin on Fri Dec 16 20:50:50 UTC 2022
PRIMARY
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