bupropion   Click here for help

GtoPdb Ligand ID: 7135

Synonyms: amfebutamone | BW-323 | Wellbutrin® | Zyban®
Approved drug
bupropion is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: The approval status for use of this drug was submitted for re-evaluation by the European Medicines Agency in 2002, following public health concerns around serious adverse reactions associated with its use. These included depression, suicidal thoughts, suicide, seizures, undesirable cardiovascular effects, and angioedema. EU Member States regulatory authorities agreed to keep the product under regular review.
Marketed formulations usually contain bupropion hydrochloride (PubChem CID 62884).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 29.1
Molecular weight 239.11
XLogP 3.63
No. Lipinski's rules broken 0
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Canonical SMILES Clc1cccc(c1)C(=O)C(NC(C)(C)C)C
Isomeric SMILES Clc1cccc(c1)C(=O)C(NC(C)(C)C)C
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
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Summary of Clinical Use Click here for help
Bupropion is used to aid smoking cessation (in combination with motivational support) in nicotine-dependent patients. Some countries authorise use for additional indications eg major depressive disorder in the US and Canada and seasonal affective disorder in Canada.
In September 2014 the US FDA approved Contrave® (bupropion and naloxone), a fixed-mixture medication, to be used in conjunction with reduced-calorie intake and physical activity, as a treatment for chronic weight management.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mode of action of bupirion in smoking cessation is not completely understood., but appears to involve inhibition of serotonin and dopamine reuptake.
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