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
SMILES
OC(=O)\C=C/C(O)=O.CC(NC(C)(C)C)C(=O)C1=CC=CC(Cl)=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-
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 | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
550.0 nM [IC50] | |||
443.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | WELLBUTRIN Approved UseINDICATIONS & 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 Date1985 |
|||
Primary | ZYBAN Approved UseZyban is indicated as an aid to smoking cessation treatment. Launch Date1985 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
93 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
|
134 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
469 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
|
688 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
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 |
|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... Other AEs: Seizures (2.8%) Sources: |
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%) Other AEs:Gastrointestinal disturbance (2.1%) Neurological disorder NOS (1.7%) Skin and subcutaneous tissue disorders (1.4%) Neuropsychiatric symptoms Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021515_Wellbutrin_biopharmr.PDF Page: 30.0 |
inconclusive | |||
Page: 15.0 |
yes [IC50 9.3 uM] | |||
Page: 90.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021515_Wellbutrin_biopharmr.PDF Page: 30.0 |
inconclusive | |||
Page: 4, 43 |
likely | |||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
Page: 10.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 46.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Antidepressants upregulate messenger RNA levels of the neuroprotective enzyme superoxide dismutase (SOD1). | 2000 Jan |
|
Mania with bupropion: a dose-related phenomenon? | 2000 May |
|
Algorithm for the treatment of chronic depression. | 2001 |
|
Strategies for the treatment of antidepressant-related sexual dysfunction. | 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 |
|
Overview of current therapies. | 2001 |
|
[Bupropion: a new hope for smokers willing to quit]. | 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 |
|
Techniques for smoking cessation: what really works? | 2001 Feb |
|
A free smoking intervention clinic initiated by medical students. | 2001 Feb |
|
Effects of bupropion sustained-release on sexual functioning and nocturnal erections in healthy men. | 2001 Feb |
|
A preliminary study of bupropion sustained-release for smoking cessation in patients with chronic posttraumatic stress disorder. | 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 |
|
Bupropion for smokers. Bupropion may not be as good as editorial implies. | 2001 Feb 17 |
|
Bupropion for smokers. Where are practices supposed to find money for bupropion? | 2001 Feb 17 |
|
[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 |
|
[A drug for smoking cessation?]. | 2001 Jan |
|
Pediatric psychopharmacology. | 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 |
|
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 |
|
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 |
|
Smoking cessation in the hospitalized patient using the transtheoretical model of behavior change. | 2001 Mar-Apr |
|
Bupropion SR worsens mood during marijuana withdrawal in humans. | 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 |
|
Smoking cessation in patients with chronic obstructive pulmonary disease: a double-blind, placebo-controlled, randomised trial. | 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 |
|
Pharmacological aids for smoking cessation. | 2001 Spring |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17477919
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
Edited
Mon Mar 31 21:41:50 GMT 2025
by
admin
on
Mon Mar 31 21:41:50 GMT 2025
|
Record UNII |
26NV8NXO4A
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
1013636-49-1
Created by
admin on Mon Mar 31 21:41:50 GMT 2025 , Edited by admin on Mon Mar 31 21:41:50 GMT 2025
|
NON-SPECIFIC STOICHIOMETRY | |||
|
93109-98-9
Created by
admin on Mon Mar 31 21:41:50 GMT 2025 , Edited by admin on Mon Mar 31 21:41:50 GMT 2025
|
PRIMARY | |||
|
26NV8NXO4A
Created by
admin on Mon Mar 31 21:41:50 GMT 2025 , Edited by admin on Mon Mar 31 21:41:50 GMT 2025
|
PRIMARY | |||
|
12882211
Created by
admin on Mon Mar 31 21:41:50 GMT 2025 , Edited by admin on Mon Mar 31 21:41:50 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
PARENT -> SALT/SOLVATE |