Identification

Name
Bupropion
Accession Number
DB01156  (APRD00621)
Type
Small Molecule
Groups
Approved
Description

A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment.

Structure
Thumb
Synonyms
  • Amfebutamone
External IDs
34841-39-9
Product Ingredients
IngredientUNIICASInChI Key
Bupropion hydrobromideE70G3G5863905818-69-1WSTCENNATOVXKQ-UHFFFAOYSA-N
Bupropion hydrochlorideZG7E5POY8O31677-93-7HEYVINCGKDONRU-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Bupropion XLTablet, extended release300 mgOralActavis Pharma Company2016-05-03Not applicableCanada
Act Bupropion XLTablet, extended release150 mgOralActavis Pharma Company2016-05-03Not applicableCanada
AplenzinTablet, extended release348 mg/1OralValeant Pharmaceuticals North America2008-04-23Not applicableUs
AplenzinTablet, extended release522 mg/1OralSanofi Aventis2009-03-30Not applicableUs
AplenzinTablet, extended release174 mg/1OralValeant Pharmaceuticals North America2008-04-23Not applicableUs
AplenzinTablet, extended release348 mg/1OralSanofi Aventis2009-03-302017-03-31Us
AplenzinTablet, extended release522 mg/1OralValeant Pharmaceuticals North America2008-04-23Not applicableUs
AplenzinTablet, extended release174 mg/1OralSanofi Aventis2009-03-302017-03-31Us
Aplenzin ERTablet, extended release348 mg/1OralStat Rx USA2009-03-30Not applicableUs
Bupropion HCl SRTablet, extended release150 mgOralValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ava-bupropion SRTablet, extended release150 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-bupropion SRTablet, extended release100 mgOralAvanstra Inc2011-09-192014-08-21Canada
BudeprionTablet, extended release150 mg/1Oralbryant ranch prepack2008-05-30Not applicableUs
BudeprionTablet, extended release150 mg/1OralTeva2008-05-302013-01-31Us
Budeprion SRTablet, extended release150 mg/1Oralbryant ranch prepack2004-03-23Not applicableUs63629 287320180907 15195 eiqila
Budeprion SRTablet, extended release150 mg/1OralTeva2004-03-232015-01-31Us0093 550220180907 15195 1xj1wgn
Budeprion SRTablet, extended release150 mg/1OralCardinal Health2004-03-222012-02-29Us00093 5502 01 nlmimage10 742dba1d
Budeprion SRTablet, extended release100 mg/1OralCardinal Health2004-01-282012-03-31Us00093 5501 01 nlmimage10 cf2d679b
Budeprion SRTablet, extended release100 mg/1OralTeva2004-02-192014-10-31Us0093 550120180907 15195 65j61g
Budeprion XLTablet, film coated, extended release150 mg/1OralStat Rx USA2006-12-14Not applicableUs10370 0101 50 nlmimage10 a03fd01e
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ContraveBupropion hydrochloride (90 mg) + Naltrexone hydrochloride (8 mg)Tablet, extended releaseOralValeant Canada Lp Valeant Canada S.E.C.2018-03-16Not applicableCanada
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralA-S Medication Solutions2014-09-10Not applicableUs
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralTakeda2014-09-10Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralPD-Rx Pharmaceuticals, Inc.2014-10-22Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralA-S Medication Solutions2014-09-10Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralNalpropion Pharmaceuticals, Inc.2014-10-22Not applicableUs
Naltrexone Hydrochloride and Bupropion Hydrochloride Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralAbbvie2014-10-22Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AppbutamoneBupropion hydrochloride (75 mg/1) + L-Tyrosine (100 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Appbutamone-DBupropion hydrochloride (75 mg/1) + L-Tyrosine (100 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Bupropion HydrochlorideBupropion hydrochloride (300 mg/1)Tablet, extended releaseOralWatson Laboratories, Inc.2007-10-252007-10-25Us
International/Other Brands
Elontril / Forfivo / Prexaton / Voxra
Categories
UNII
01ZG3TPX31
CAS number
34911-55-2
Weight
Average: 239.741
Monoisotopic: 239.10769191
Chemical Formula
C13H18ClNO
InChI Key
SNPPWIUOZRMYNY-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
SMILES
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

Pharmacology

Indication

For the treatment of depression and as aid to smoking cessation.

Associated Conditions
Associated Therapies
Pharmacodynamics

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.

Mechanism of action

Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Human
ASodium-dependent noradrenaline transporter
inhibitor
Human
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Human
Absorption

For sustained release, peak plasma concentrations are achieved within 3 hours.

Volume of distribution
Not Available
Protein binding

84 %

Metabolism

Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion.

Route of elimination

Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.

Half life

24 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
D(2) dopamine receptor---(C;C)C Allele, homozygousEffect Directly StudiedThe presence of this genotype in DRD2 is associated with improved therapeutic response to bupropion.Details

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Bupropion is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
1,10-PhenanthrolineThe therapeutic efficacy of Bupropion can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Bupropion.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Bupropion is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbirateroneThe serum concentration of Bupropion can be increased when it is combined with Abiraterone.
Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take without regard to meals.

References

Synthesis Reference
US3819706
General References
  1. Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [PubMed:9862757]
  2. Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. [PubMed:16027765]
  3. Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. [PubMed:16086611]
  4. Authors unspecified: Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. [PubMed:1684162]
  5. Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [PubMed:16974189]
External Links
Human Metabolome Database
HMDB0001510
KEGG Drug
D07591
KEGG Compound
C06860
PubChem Compound
444
PubChem Substance
46506896
ChemSpider
431
BindingDB
50048392
ChEBI
3219
ChEMBL
CHEMBL894
Therapeutic Targets Database
DAP000052
PharmGKB
PA448687
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Bupropion
ATC Codes
A08AA62 — Bupropion and naltrexoneN06AX12 — Bupropion
AHFS Codes
  • 28:16.04.92 — Miscellaneous Antidepressants
FDA label
Download (88.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceCocaine Use Disorders1
0CompletedTreatmentStress Disorders, Posttraumatic / Tobacco Use Disorders1
0RecruitingPreventionCurrent Smokers / Head and Neck Squamous Cell Carcinoma (HNSCC) / Hypopharyngeal Squamous Cell Carcinoma / Laryngeal Squamous Cell Carcinoma / Nasopharyngeal Carcinoma / Oral Cavity Squamous Cell Carcinoma / Oropharyngeal Squamous Cell Carcinoma1
0RecruitingTreatmentMajor Depressive Disorder (MDD) / Unipolar Depression1
1Active Not RecruitingOtherLeukemia, Lymphocytic, Chronic, B-Cell1
1CompletedNot AvailableHealthy Volunteers7
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Bupropion / Pharmacokinetics of Isavuconazole1
1CompletedNot AvailableNicotine Dependence / Tobacco Dependence1
1CompletedBasic ScienceAlzheimer's Disease (AD) / Metabolism1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Substance-Related Disorders1
1CompletedDiagnosticDrug Interactions1
1CompletedDiagnosticHealthy Volunteers1
1CompletedDiagnosticMethamphetamine Dependence1
1CompletedDiagnosticNicotine Dependence1
1CompletedPreventionDepression / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHealthy Volunteers / Type 2 Diabetes Mellitus1
1CompletedTreatmentMajor Depressive Disorder (MDD)2
1CompletedTreatmentMoods Disorders1
1CompletedTreatmentSmoking1
1CompletedTreatmentTobacco Use Disorders1
1CompletedTreatmentTuberculosis / Tuberculosis, Pulmonary1
1TerminatedNot AvailableDepressive Disorders1
1TerminatedTreatmentCocaine-Related Disorders1
1Unknown StatusBasic ScienceSubstance-Related Disorders1
1Unknown StatusDiagnosticAmphetamine-Related Disorders1
1, 2CompletedTreatmentBipolar Disorder (BD)1
1, 2CompletedTreatmentNicotine Dependence / Smoking1
1, 2TerminatedTreatmentHead and Neck Carcinoma1
1, 2WithdrawnSupportive CareLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2CompletedNot AvailableBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
2CompletedTreatmentAdolescent Methamphetamine Abuse1
2CompletedTreatmentAlcoholism / Smoking1
2CompletedTreatmentAmphetamine Dependence / Methamphetamine / Methamphetamine Dependence / Pharmacogenetics / Substance Abuse1
2CompletedTreatmentAmphetamine-Related Disorders1
2CompletedTreatmentApathy / Huntington's Disease (HD)1
2CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Nicotine Dependence1
2CompletedTreatmentBMI >30 kg/m22
2CompletedTreatmentBinge Drinking1
2CompletedTreatmentBipolar Disorder (BD) / Depressive Disorders1
2CompletedTreatmentCessation, Smoking1
2CompletedTreatmentCessation, Smoking / Pregnancy1
2CompletedTreatmentCessation, Smoking / Schizophrenic Disorders1
2CompletedTreatmentDependence, Cocaine / Major Depressive Disorder (MDD)1
2CompletedTreatmentDepressive Disorders1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Substance Abuse1
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentMarijuana Abuse / Substance-Related Disorders1
2CompletedTreatmentMethamphetamine1
2CompletedTreatmentMethamphetamine Dependence1
2CompletedTreatmentNicotine Dependence1
2CompletedTreatmentSchizophrenia and Disorders With Psychotic Features / Tobacco Use Disorders1
2CompletedTreatmentSchizophrenic Disorders / Tobacco Use Cessation / Tobacco Use Disorders1
2CompletedTreatmentSchizophrenic Disorders / Tobacco Use Disorders1
2CompletedTreatmentSmoking Lapse Behavior1
2CompletedTreatmentSmoking, Cigarette1
2CompletedTreatmentTobacco Use Disorders2
2Not Yet RecruitingTreatmentAnhedonia / Cessation, Smoking / Cessation, Tobacco / Smoking (Tobacco) Addiction / Tobacco Smoking1
2Not Yet RecruitingTreatmentCessation, Smoking / Nicotine Dependence / Smoking, Cigarette2
2RecruitingSupportive CareCarcinoma, Breast / Cervical Carcinoma / One to five years postmenopausal / Ovarian Carcinoma / Uterine Corpus Cancer / Vaginal Carcinoma / Vulvar Carcinoma1
2RecruitingTreatmentAlcohol Abuse1
2RecruitingTreatmentErectile Dysfunctions / Hypoactive Sexual Desire Disorder (HSDD) / Sexual Dysfunctions, Psychological1
2RecruitingTreatmentMajor Depressive Disorder (MDD)1
2RecruitingTreatmentNicotine Dependence / Smoking1
2Unknown StatusTreatmentTobacco Use Cessation / Tobacco Use Disorders1
2, 3Active Not RecruitingTreatmentCessation, Smoking / Tobacco Use Disorders1
2, 3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Dependence, Cocaine / Opioid-Related Disorders1
2, 3CompletedTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
2, 3CompletedTreatmentCrohn's Disease (CD)1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3CompletedTreatmentNicotine Dependence / Nicotine Withdrawal1
2, 3CompletedTreatmentOrgasmic Disorder1
2, 3CompletedTreatmentRestless Legs Syndrome (RLS)1
2, 3CompletedTreatmentSmoking1
2, 3CompletedTreatmentSmoking / Stress Disorders, Post-Traumatic1
2, 3Enrolling by InvitationTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m22
2, 3RecruitingTreatmentAgitation in Patients With Dementia of the Alzheimer's Type / Alzheimer's Disease (AD) / Psychomotor Agitation1
2, 3RecruitingTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
2, 3RecruitingTreatmentDependence, Cocaine / Substance Abuse1
2, 3TerminatedTreatmentNicotine Dependence / Smoking, Cigarette1
2, 3TerminatedTreatmentTobacco Dependence1
2, 3Unknown StatusTreatmentTobacco Use Disorders1
3Active Not RecruitingTreatmentCessation, Smoking1
3Active Not RecruitingTreatmentNicotine Dependence / Tobacco Use1
3CompletedNot AvailableUnipolar Depression1
3CompletedPreventionLung Cancers1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Myocardial Infarction / Smoking1
3CompletedTreatmentApathy in Dementia1
3CompletedTreatmentCessation, Smoking1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD) / Unipolar Depression1
3CompletedTreatmentMajor Depressive Disorder (MDD)4
3CompletedTreatmentNicotine Dependence3
3CompletedTreatmentSmokeless Tobacco1
3CompletedTreatmentSmoking1
3CompletedTreatmentTobacco Use Disorders3
3Not Yet RecruitingTreatmentCessation, Smoking / Human Immunodeficiency Virus (HIV) / Opioid Dependence1
3RecruitingTreatmentBMI >30 kg/m21
3RecruitingTreatmentBipolar I Disorder1
3RecruitingTreatmentTreatment Resistant Major Depressive Disorder1
3TerminatedPreventionLung Cancers1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentBMI >27 kg/m2 / BMI >30 kg/m21
3Unknown StatusTreatmentAlcohol-Related Disorders / Cessation, Smoking1
4Active Not RecruitingTreatmentCessation, Smoking / Nicotine Addiction / Smoking, Cigarette1
4Active Not RecruitingTreatmentHomelessness / Tobacco Use Disorders1
4CompletedNot AvailableCessation, Smoking1
4CompletedNot AvailableRoux En Y Gastric Bypass1
4CompletedBasic ScienceDepression1
4CompletedBasic ScienceNicotine Dependence1
4CompletedHealth Services ResearchHealthy Volunteers1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionCerebrovascular Disorders / Cessation, Smoking1
4CompletedSupportive CareFriedreich's Ataxia1
4CompletedTreatmentAlcoholism / Smoking1
4CompletedTreatmentApathy / Depression / Sexual Dysfunctions / Side Effects1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Cannabis Use Disorders / Nicotine Dependence1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
4CompletedTreatmentCancer, Breast / Major Depressive Disorder (MDD)1
4CompletedTreatmentCardiovascular Disease (CVD) / Myocardial Infarction / Smoking / Unstable Angina (UA)1
4CompletedTreatmentCessation, Smoking3
4CompletedTreatmentCessation, Smoking / Smoking / Tobacco Use Disorders1
4CompletedTreatmentCigarette-smoking / Obese / Schizophrenic Disorders1
4CompletedTreatmentDepression2
4CompletedTreatmentDepression / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4CompletedTreatmentDepression / Suicidal Ideation1
4CompletedTreatmentDepressive illness1
4CompletedTreatmentDysthymic Disorder1
4CompletedTreatmentDysthymic Disorder / Major Depressive Disorder (MDD)2
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentInflammatory Bowel Diseases (IBD) / Sleep Disturbances / Tiredness1
4CompletedTreatmentMajor Depressive Disorder (MDD)3
4CompletedTreatmentNicotine Dependence1
4CompletedTreatmentPregnancy Related / Tobacco Use Disorders1
4CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders / Tobacco-Use Disorder1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentSleep disorders and disturbances / Tobacco Use Cessation1
4CompletedTreatmentSmoking2
4CompletedTreatmentTobacco Dependence1
4CompletedTreatmentTobacco Use Disorders2
4Not Yet RecruitingTreatmentAcute Agitation / Aggressive Behavior / Psychiatric Emergency1
4Not Yet RecruitingTreatmentDiagnosis and Treatment of Depression1
4Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
4RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4RecruitingBasic ScienceType 2 Diabetes Mellitus1
4RecruitingDiagnosticAsthma Bronchial / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)1
4RecruitingTreatmentBMI >30 kg/m21
4RecruitingTreatmentBMI >30 kg/m2 / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
4RecruitingTreatmentDepressive Disorders1
4RecruitingTreatmentGeriatric Depression / Late Life Depression (LLD) / Major Depressive Disorder (MDD) / Treatment Resistant Depression (TRD) / Treatment-Refractory Depression1
4RecruitingTreatmentSchizophrenic Disorders / Smoking, Cigarette1
4TerminatedTreatmentBMI >30 kg/m2 / Cardiovascular Disease (CVD)1
4TerminatedTreatmentBipolar Disorder (BD) / Depression1
4TerminatedTreatmentDepression1
4TerminatedTreatmentEnd Stage Renal Disease (ESRD) / Major Depressive Disorder (MDD)1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4TerminatedTreatmentNicotine Dependence / Sleeplessness1
4TerminatedTreatmentTobacco Use Disorders1
4Unknown StatusTreatmentAlcoholism / Depression / Suicidal Behaviour1
4Unknown StatusTreatmentBipolar Disorder (BD)1
4Unknown StatusTreatmentDepression2
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD) / Nicotine Dependence1
4WithdrawnTreatmentDepressive Disorder Not Otherwise Specified (NOS) / Dysthymic Disorder / Major Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingOtherMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingTreatmentCessation, Smoking / Health Behavior / Lifestyle-related Condition1
Not AvailableCompletedNot AvailableCancer and Tobacco Abuse1
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableCompletedBasic ScienceDepression1
Not AvailableCompletedPreventionBMI >27 kg/m2 / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedPreventionBipolar Disorder (BD) / Depression / Psychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedPreventionCancer Survivors / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedScreeningAcute Coronary Syndromes (ACS) / Depressive Symptoms1
Not AvailableCompletedTreatmentAlcohol Drinking / Attention Deficit Disorder (ADD) / Cessation, Smoking / Depression1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Substance Use Disorder (SUD)1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentCocaine-Related Disorders1
Not AvailableCompletedTreatmentGambling / Pathological Gambling1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHomeless Persons / Smoking1
Not AvailableCompletedTreatmentMarijuana Abuse / Smoking, Cigarette1
Not AvailableCompletedTreatmentNicotine Dependence1
Not AvailableCompletedTreatmentNicotine Dependence / Tobacco Use Disorders1
Not AvailableCompletedTreatmentPTSD / Smoking1
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableCompletedTreatmentSmoking1
Not AvailableCompletedTreatmentTobacco Use Disorders1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableEnrolling by InvitationNot AvailableCessation, Smoking1
Not AvailableEnrolling by InvitationTreatmentNicotine Dependence / Smokeless Tobacco1
Not AvailableRecruitingNot AvailableDepression1
Not AvailableRecruitingNot AvailableDepression / Suicidal Ideation1
Not AvailableRecruitingBasic ScienceAdverse Effect of Drug Therapy Metabolism Medications (Diagnosis)1
Not AvailableRecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Nicotine Dependence1
Not AvailableRecruitingTreatmentAlcohol Drinking / Cessation, Smoking1
Not AvailableRecruitingTreatmentAntidepressant Drug Adverse Reaction / Depression1
Not AvailableRecruitingTreatmentCessation, Smoking / Genetic Predisposition1
Not AvailableTerminatedNot AvailableSmoking1
Not AvailableUnknown StatusNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusDiagnosticTobacco Use Disorders1
Not AvailableUnknown StatusTreatmentCessation, Smoking1
Not AvailableUnknown StatusTreatmentCessation, Smoking / Smoking1
Not AvailableUnknown StatusTreatmentMethamphetamine Use Disorder1
Not AvailableUnknown StatusTreatmentNicotine Dependence / Nicotine Use Disorder1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • American Nutriceuticals Inc.
  • Amerisource Health Services Corp.
  • Anchen Pharmaceuticals Inc.
  • Apotex Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Biovail Pharmaceuticals
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • Cardinal Health
  • Catalent Pharma Solutions
  • CMIC-VPS Corp.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSM Corp.
  • Eon Labs
  • GlaxoSmithKline Inc.
  • Global Pharmaceuticals
  • Golden State Medical Supply Inc.
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Innoviant Pharmacy Inc.
  • Jackson Medical Inc.
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacy Service Center
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Professional Co.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Spectrum Chemicals and Laboratory Products
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, extended releaseOral174 mg/1
Tablet, extended releaseOral522 mg/1
Tablet, extended releaseOral348 mg/1
Kit
Tablet, film coated, extended releaseOral150 mg/1
TabletOcclusive dressing technique150 mg/1
TabletOral100 mg/1
TabletOral75 mg/1
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral150 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, film coatedOcclusive dressing technique75 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral75 mg/1
Tablet, film coated, extended releaseOcclusive dressing technique150 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral200 mg/1
TabletOral150 mg/1
Tablet, extended releaseOral300 mg/1
Tablet, film coated, extended releaseOral300 mg/1
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
Tablet, extended releaseOral450 mg/1
Tablet, film coated, extended releaseOral450 mg/1
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral200 mg/1
Tablet, extended releaseOral300 mg
Prices
Unit descriptionCostUnit
Aplenzin er 522 mg tablet16.74USD tablet
Bupropion hydrochloride powder10.2USD g
Wellbutrin XL 300 mg 24 Hour tablet9.03USD tablet
Wellbutrin xl 300 mg tablet8.68USD tablet
Wellbutrin SR 200 mg 12 Hour tablet7.57USD tablet
Aplenzin er 348 mg tablet7.36USD tablet
Wellbutrin sr 200 mg tablet7.27USD tablet
Wellbutrin XL 150 mg 24 Hour tablet6.84USD tablet
Wellbutrin xl 150 mg tablet6.58USD tablet
Aplenzin er 174 mg tablet5.58USD tablet
BuPROPion HCl 300 mg 24 Hour tablet4.96USD tablet
Wellbutrin SR 150 mg 12 Hour tablet4.07USD tablet
BuPROPion HCl 200 mg 12 Hour tablet3.99USD tablet
Wellbutrin sr 150 mg tablet3.92USD tablet
Zyban 150 mg 12 Hour tablet3.88USD tablet
Wellbutrin SR 100 mg 12 Hour tablet3.8USD tablet
Zyban sr 150 mg tablet3.73USD tablet
Wellbutrin sr 100 mg tablet3.66USD tablet
Wellbutrin 100 mg tablet3.62USD tablet
BuPROPion HCl 150 mg 12 Hour tablet3.02USD tablet
Wellbutrin 75 mg tablet2.71USD tablet
BuPROPion HCl (Smoking Deter) 150 mg 12 Hour tablet2.01USD tablet
Wellbutrin Xl 300 mg Extended-Release Tablet1.12USD tablet
Bupropion hcl 100 mg tablet0.98USD tablet
Wellbutrin Sr 150 mg Sustained-Release Tablet0.96USD tablet
Bupropion hcl 75 mg tablet0.74USD tablet
Wellbutrin Xl 150 mg Extended-Release Tablet0.56USD tablet
Pms-Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Ratio-Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Sandoz Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Sandoz Bupropion Sr 100 mg Sustained-Release Tablet0.35USD tablet
Ratio-Bupropion Sr 100 mg Sustained-Release Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5358970No1993-08-122013-08-12Us
CA2524300No2008-10-282023-08-08Canada
CA2168364No2001-09-182014-07-29Canada
US7569610No2006-06-272026-06-27Us
US7662407No2006-06-272026-06-27Us
US7241805No2006-06-272026-06-27Us
US7649019No2006-06-272026-06-27Us
US7645802No2006-06-272026-06-27Us
US7671094No2006-06-272026-06-27Us
US7572935No2006-06-272026-06-27Us
US7585897No2006-06-272026-06-27Us
US6096341No1998-10-302018-10-30Us
US7674479No2007-06-252027-06-25Us
US8722085No2007-11-082027-11-08Us
US8318788No2007-11-082027-11-08Us
US7462626No2004-07-202024-07-20Us
US8815889No2004-07-202024-07-20Us
US9107837No2007-06-042027-06-04Us
US9125868No2007-11-082027-11-08Us
US8916195No2010-02-022030-02-02Us
US9248123No2012-01-132032-01-13Us
US8088786No2009-02-032029-02-03Us
US7375111No2005-03-262025-03-26Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)233-234 °CNot Available
water solubility312 mg/mlNot Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0693 mg/mLALOGPS
logP3.28ALOGPS
logP3.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)18.29ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.7 m3·mol-1ChemAxon
Polarizability25.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.975
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.733
P-glycoprotein inhibitor INon-inhibitor0.8738
P-glycoprotein inhibitor IINon-inhibitor0.9343
Renal organic cation transporterNon-inhibitor0.8814
CYP450 2C9 substrateNon-substrate0.785
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.574
CYP450 1A2 substrateNon-inhibitor0.7499
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.7743
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5141
Ames testNon AMES toxic0.9233
CarcinogenicityNon-carcinogens0.5609
BiodegradationNot ready biodegradable0.9892
Rat acute toxicity2.4363 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9684
hERG inhibition (predictor II)Non-inhibitor0.8886
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-c10af1c8e3619fe0bffc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-55448af4d9a8ce866a88
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2883ba18321a8b8228a1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-7d6cad849706146ddab3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-0fca8999746b69ee4fc1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-b64f8d2b50bede574f63
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2edefa63d5f6f1b08db7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-b8ea1de058a84547700d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0910000000-6f471b9150fb1b7f6fcc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-cc966137ee3283828af7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00lr-0900000000-7f86f38f740aa41b244b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e7f2cfdbabbd35a9b643
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-4daf0e10db1e5f2750bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-f77a450be176593153d2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00m0-0910000000-d2eb7265b058766459c9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0910000000-fa2592b7296c7561333c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-4d831e97d7e7dfff141b

Taxonomy

Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Chlorobenzenes / Aryl chlorides / Alpha-amino ketones / Dialkylamines / Organopnictogen compounds / Organochlorides / Organic oxides
show 1 more
Substituents
Alkyl-phenylketone / Phenylpropane / Benzoyl / Aryl alkyl ketone / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, monochlorobenzenes, propanone, aromatic ketone (CHEBI:3219)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Miller DK, Sumithran SP, Dwoskin LP: Bupropion inhibits nicotine-evoked [(3)H]overflow from rat striatal slices preloaded with [(3)H]dopamine and from rat hippocampal slices preloaded with [(3)H]norepinephrine. J Pharmacol Exp Ther. 2002 Sep;302(3):1113-22. [PubMed:12183670]
  2. Meyer JH, Goulding VS, Wilson AA, Hussey D, Christensen BK, Houle S: Bupropion occupancy of the dopamine transporter is low during clinical treatment. Psychopharmacology (Berl). 2002 Aug;163(1):102-5. Epub 2002 Jul 13. [PubMed:12185406]
  3. Kugaya A, Seneca NM, Snyder PJ, Williams SA, Malison RT, Baldwin RM, Seibyl JP, Innis RB: Changes in human in vivo serotonin and dopamine transporter availabilities during chronic antidepressant administration. Neuropsychopharmacology. 2003 Feb;28(2):413-20. Epub 2002 Jul 19. [PubMed:12589396]
  4. Learned-Coughlin SM, Bergstrom M, Savitcheva I, Ascher J, Schmith VD, Langstrom B: In vivo activity of bupropion at the human dopamine transporter as measured by positron emission tomography. Biol Psychiatry. 2003 Oct 15;54(8):800-5. [PubMed:14550679]
  5. Szabo Z, Argyelan M, Kanyo B, Pavics L, Janka Z: [Change of dopamine transporter activity (DAT) during the action of bupropion (in depression)]. Neuropsychopharmacol Hung. 2004 Jun;6(2):79-81. [PubMed:15787205]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  8. Stahl SM, Pradko JF, Haight BR, Modell JG, Rockett CB, Learned-Coughlin S: A Review of the Neuropharmacology of Bupropion, a Dual Norepinephrine and Dopamine Reuptake Inhibitor. Prim Care Companion J Clin Psychiatry. 2004;6(4):159-166. [PubMed:15361919]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Bondarev ML, Bondareva TS, Young R, Glennon RA: Behavioral and biochemical investigations of bupropion metabolites. Eur J Pharmacol. 2003 Aug 1;474(1):85-93. [PubMed:12909199]
  2. Mitchell HA, Ahern TH, Liles LC, Javors MA, Weinshenker D: The effects of norepinephrine transporter inactivation on locomotor activity in mice. Biol Psychiatry. 2006 Nov 15;60(10):1046-52. Epub 2006 Aug 7. [PubMed:16893531]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Stahl SM, Pradko JF, Haight BR, Modell JG, Rockett CB, Learned-Coughlin S: A Review of the Neuropharmacology of Bupropion, a Dual Norepinephrine and Dopamine Reuptake Inhibitor. Prim Care Companion J Clin Psychiatry. 2004;6(4):159-166. [PubMed:15361919]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [PubMed:9862757]
  2. Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [PubMed:10991997]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [PubMed:11996013]
  4. Hesse LM, Venkatakrishnan K, Court MH, von Moltke LL, Duan SX, Shader RI, Greenblatt DJ: CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug Metab Dispos. 2000 Oct;28(10):1176-83. [PubMed:10997936]
  5. Jefferson JW, Pradko JF, Muir KT: Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations. Clin Ther. 2005 Nov;27(11):1685-95. [PubMed:16368442]
  6. Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [PubMed:17009913]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [PubMed:17009913]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. [PubMed:2870173]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Bergen AW, Javitz HS, Krasnow R, Michel M, Nishita D, Conti DV, Edlund CK, Kwok PY, McClure JB, Kim RB, Hall SM, Tyndale RF, Baker TB, Benowitz NL, Swan GE: Organic cation transporter variation and response to smoking cessation therapies. Nicotine Tob Res. 2014 Dec;16(12):1638-46. doi: 10.1093/ntr/ntu161. Epub 2014 Aug 20. [PubMed:25143296]
  2. FDA Center for Drug Evaluation and Research: Clinical Pharmacology and Biopharmaceutical Review(s) [File]

Drug created on June 13, 2005 07:24 / Updated on September 18, 2018 23:02