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Details

Stereochemistry RACEMIC
Molecular Formula C13H18ClNO
Molecular Weight 239.741
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPROPION

SMILES

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

InChI

InChIKey=SNPPWIUOZRMYNY-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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

Description

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 TargetPharmacologyConditionPotency
550.0 nM [IC50]
443.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
WELLBUTRIN
Primary
ZYBAN

Cmax

ValueDoseCo-administeredAnalytePopulation
134 ng/mL
100 mg single, oral
BUPROPION plasma
Homo sapiens
93 ng/mL
75 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
136 ng/mL
150 mg 2 times / day steady-state, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
91 ng/mL
150 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
688 ng × h/mL
100 mg single, oral
BUPROPION plasma
Homo sapiens
469 ng × h/mL
75 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
100 mg single, oral
BUPROPION plasma
Homo sapiens
10 h
75 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens
21 h
150 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
16%
150 mg single, oral
BUPROPION HYDROCHLORIDE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
Bupropion (10 uM) significantly decreased nicotine-evoked [(3)H]dopamine release by approximately 50% in rat striatal synaptosomes and slices.
Substance Class Chemical
Record UNII
01ZG3TPX31
Record Status Validated (UNII)
Record Version