BUPROPION

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Synonyms
Status
Molecule Category Free-form
ATC N06AX12
UNII 01ZG3TPX31
EPA CompTox DTXSID7022706

Structure

InChI Key SNPPWIUOZRMYNY-UHFFFAOYSA-N
Smiles CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H18ClNO
Molecular Weight 239.75
AlogP 3.3
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 29.1
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 16.0
Assay Description Organism Bioactivity Reference
Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radioligand None 371.54 nM
In vitro inhibition of dopamine (DA) uptake in synaptosomal preparation of rat brain Rattus norvegicus 900.0 nM
Displacement of [3H]WIN-35428 from human dopamine transporter expressed in mouse N2A cells by scintillation counting Homo sapiens 441.0 nM
Displacement of [125I]RTI55 from cloned human DAT expressed in HEK293 cells Homo sapiens 871.0 nM
Inhibition of [3H]dopamine reuptake at human DAT expressed in HEK293 cells Homo sapiens 945.0 nM
Inhibition of [3H]norepinephrine reuptake at human NET expressed in HEK293 cells Homo sapiens 443.0 nM
Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells Homo sapiens 658.0 nM
Inhibition of [3H]serotonin uptake at human SERT expressed in HEK293 cells Homo sapiens 100.0 nM
Antagonist activity at alpha3beta4 nAChR receptor in human SH-SY5Y cells assessed as inhibition of carbamylcholine-induced 86Rb+ efflux by liquid scintillation counting Homo sapiens 1.8 nM
Antagonist activity at human alpha4beta2 nAChR receptor expressed in human SH-SY5Y cells assessed as inhibition of carbamylcholine-induced 86Rb+ efflux by liquid scintillation counting Homo sapiens 12.0 nM
Antagonist activity at human alpha4beta4 nAChR receptor expressed in human SH-SY5Y cells assessed as inhibition of carbamylcholine-induced 86Rb+ efflux by liquid scintillation counting Homo sapiens 15.0 nM
Antagonist activity at alpha-1-beta-1-gamma-delta nAChR receptor expressed in human TE671/RD cells assessed as inhibition of carbamylcholine-induced 86Rb+ efflux by liquid scintillation counting Homo sapiens 7.9 nM
Inhibition of [3H]dopamine reuptake at human DAT expressed in HEK293 cells after 90 mins by scintillation counting Homo sapiens 660.0 nM
Smoke cessation activity in sc dosed ICR mouse assessed as inhibition of nicotine-induced antinociception administered 15 mins before nicotine challenge measured after 5 mins of nicotine infusion by hotplate assay Mus musculus 15.0 mg kg-1
Smoke cessation activity in sc dosed ICR mouse assessed as inhibition of nicotine-induced antinociception administered 15 mins before nicotine challenge measured after 5 mins of nicotine infusion by tail-flick assay Mus musculus 1.2 mg kg-1
Smoke cessation activity in sc dosed ICR mouse assessed as inhibition of nicotine-induced increase in locomotor activity administered 15 mins before nicotine challenge measured after 5 mins of nicotine infusion Mus musculus 4.9 mg kg-1
Smoke cessation activity in sc dosed ICR mouse assessed as inhibition of nicotine-induced hypothermia administered 15 mins before nicotine challenge measured after 30 mins of nicotine infusion Mus musculus 9.2 mg kg-1
Inhibition of human DAT expressed in HEK293 cells assessed as inhibition of [3H]DA reuptake after 10 mins by scintillation counting Homo sapiens 658.0 nM
Inhibition of nicotine-induced antinociception activity in ICR mouse assessed as latency to remove tail administered subcutaneously 15 mins prior to nicotine challenge and measured after 5 mins of 2.5 mg/kg nicotine challenge by tail-flick test Mus musculus 1.2 mg kg-1
Inhibition of nicotine-induced antinociception activity in ICR mouse assessed as paw licking and jumping latency dministered subcutaneously 15 mins prior to nicotine challenge and measured after 5 mins of 2.5 mg/kg nicotine challenge by hot plate test Mus musculus 15.0 mg kg-1
Inhibition of nicotine-induced hypolocomotion in ICR mouse assessed as number of photocell interruption dministered subcutaneously 15 mins prior to nicotine challenge and measured after 5 mins of 1.5 mg/kg nicotine challenge Mus musculus 4.9 mg kg-1
Antipyretic activity against nicotine-induced hypothermia in ICR mouse assessed as change in rectal temperature dministered subcutaneously 15 mins prior to nicotine challenge and measured after 30 mins of 2.5 mg/kg nicotine challenge Mus musculus 9.2 mg kg-1
Inhibition of nicotine-induced conditioned place preference in ICR mouse assessed as activity count and time spent in chamberdministered subcutaneously 15 mins prior to 0.5 mg/kg nicotine challenge up to 4 days using photosensors Mus musculus 0.35 mg kg-1
DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 821.4 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 8.5 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 7.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 17.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 105.6 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 108.53 %
Inhibition of DAT (unknown origin) assessed as transporter-mediated dopamine reuptake Homo sapiens 550.0 nM
Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells at 10 uM after 15 to 20 mins by microbeta scintillation counting method Homo sapiens 61.5 %
Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells at 1 uM after 15 to 20 mins by microbeta scintillation counting method Homo sapiens 78.3 %

Environmental Exposure

Environmental Exposure Map
Countries
USA

Cross References

Resources Reference
ChEBI 3219
ChEMBL CHEMBL894
DrugBank DB01156
DrugCentral 435
FDA SRS 01ZG3TPX31
Human Metabolome Database HMDB0001510
Guide to Pharmacology 7135
KEGG C06860
PharmGKB PA448687
PubChem 444
SureChEMBL SCHEMBL38777
CONTENTS