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 276.2024
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPROPION HYDROCHLORIDE

SMILES

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

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 ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

504748800000
Primary
ZYBAN

Approved Use

Zyban is indicated as an aid to smoking cessation treatment.

Launch Date

504748800000
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
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Seizures...
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
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
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Neuropsychiatric symptoms
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Skin and subcutaneous tissue disorders 1.4%
Disc. AE
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Neurological disorder NOS 1.7%
Disc. AE
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Gastrointestinal disturbance 2.1%
Disc. AE
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Neuropsychiatric symptoms 3%
Disc. AE
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
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
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
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing
PubMed

PubMed

TitleDatePubMed
Algorithm for the treatment of chronic depression.
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: a potential problem with the new 'miracle' anti-smoking drug.
2001 Apr
[Pharmacologic therapy for smoking cessation].
2001 Apr
[Bupropion: a new hope for smokers willing to quit].
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
Effects of bupropion SR on anterior paralimbic function during waking and REM sleep in depression: preliminary findings using.
2001 Apr 10
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
[Zyban and medical ethics].
2001 Feb 28
Treating nicotine dependence.
2001 Jan-Feb
Single-dose pharmacokinetics of bupropion in adolescents: effects of smoking status and gender.
2001 Jul
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
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
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
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
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
Substitution of an SSRI with bupropion sustained release following SSRI-induced sexual dysfunction.
2001 Mar
Bupropion sustained release in adolescents with comorbid attention-deficit/hyperactivity disorder and depression.
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
Ondansetron rather than metoclopramide for bupropion-induced nausea.
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
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

The usual adult dose is 300 mg/day, given 3 times daily. Dosing
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 21:05:45 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:45 UTC 2021
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 [MI]
Common Name English
BUPROPION HYDROCHLORIDE [USP-RS]
Common Name English
NSC-315851
Code English
BUPROPION HYDROCHLORIDE [USP]
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 [USAN]
Common Name English
BUPROPION HCL
Common Name English
BUPROPION HYDROCHLORIDE [MART.]
Common Name English
BUPROPION HYDROCHLORIDE [WHO-DD]
Common Name English
AMFEBUTAMONE HYDROCHLORIDE
Common Name English
BUPROPION HYDROCHLORIDE [HSDB]
Common Name English
BW 323
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 Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
EMA ASSESSMENT REPORTS MYSIMBA (AUTHORIZED: OBESITY)
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
NCI_THESAURUS C265
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
Code System Code Type Description
MERCK INDEX
M2773
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY Merck Index
PUBCHEM
62884
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
FDA UNII
ZG7E5POY8O
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
DRUG BANK
DBSALT000199
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
USP_CATALOG
1078733
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY USP-RS
CAS
31677-93-7
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
EVMPD
SUB00432MIG
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
RXCUI
203204
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY RxNorm
EPA CompTox
31677-93-7
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
250-759-9
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL894
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
NCI_THESAURUS
C1317
Created by admin on Fri Jun 25 21:05:45 UTC 2021 , Edited by admin on Fri Jun 25 21:05:45 UTC 2021
PRIMARY
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