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
1. Carroll FI, Blough BE, Abraham P, Mills AC, Holleman JA, Wolckenhauer SA, Decker AM, Landavazo A, McElroy KT, Navarro HA et al.. (2009)
Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction.
J Med Chem, 52 (21): 6768-81. [PMID:19821577]
2. Lapinsky DJ, Aggarwal S, Huang Y, Surratt CK, Lever JR, Foster JD, Vaughan RA. (2009)
A novel photoaffinity ligand for the dopamine transporter based on pyrovalerone.
Bioorg Med Chem, 17 (11): 3770-4. [PMID:19442525]