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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(Cl)=CC=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 C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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 ( + / - )

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
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
Bupropion mimics a transient ischemic attack.
1999 Mar
Antidepressants upregulate messenger RNA levels of the neuroprotective enzyme superoxide dismutase (SOD1).
2000 Jan
Mania with bupropion: a dose-related phenomenon?
2000 May
[Bupropion: a new hope for smokers willing to quit].
2001 Apr
Does pretreatment anxiety predict response to either bupropion SR or sertraline?
2001 Apr
Evaluation of the contribution of cytochrome P450 3A4 to human liver microsomal bupropion hydroxylation.
2001 Aug
Effects of bupropion sustained-release on sexual functioning and nocturnal erections in healthy men.
2001 Feb
A controlled clinical trial of bupropion for attention deficit hyperactivity disorder in adults.
2001 Feb
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. New products for smoking cessation maintain profile of smoking cessation services.
2001 Feb 17
Antismoking drug comes under scrutiny after deaths.
2001 Feb 24
[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
[Bupropion: an effective new aid for smoking cessation].
2001 Jan 13
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
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
The Stanley Foundation Bipolar Network. I. Rationale and methods.
2001 Jun
Depression and anxiety disorders.
2001 Jun
Bupropion-induced erythema multiforme.
2001 Jun
Variations in treatment benefits influence smoking cessation: results of a randomised controlled trial.
2001 Jun
A practical guide to tobacco cessation in dental offices.
2001 Mar
Bupropion SR worsens mood during marijuana withdrawal in humans.
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
Use of bupropion SR in a pharmacist-managed outpatient smoking-cessation program.
2001 May
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
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 Sat Dec 16 07:32:48 UTC 2023
Edited
by admin
on Sat Dec 16 07:32:48 UTC 2023
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 Sat Dec 16 07:32:48 UTC 2023 , Edited by admin on Sat Dec 16 07:32:48 UTC 2023
NON-SPECIFIC STOICHIOMETRY
CAS
93109-98-9
Created by admin on Sat Dec 16 07:32:48 UTC 2023 , Edited by admin on Sat Dec 16 07:32:48 UTC 2023
PRIMARY
FDA UNII
26NV8NXO4A
Created by admin on Sat Dec 16 07:32:48 UTC 2023 , Edited by admin on Sat Dec 16 07:32:48 UTC 2023
PRIMARY
PUBCHEM
12882211
Created by admin on Sat Dec 16 07:32:48 UTC 2023 , Edited by admin on Sat Dec 16 07:32:48 UTC 2023
PRIMARY
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