MODAFINIL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N06BA07
UNII R3UK8X3U3D
EPA CompTox DTXSID0023329

Structure

InChI Key YFGHCGITMMYXAQ-UHFFFAOYSA-N
Smiles NC(=O)C[S+]([O-])C(c1ccccc1)c1ccccc1
InChI
InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H15NO2S
Molecular Weight 273.36
AlogP 2.01
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 60.16
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Dopamine transporter inhibitor INHIBITOR DailyMed PubMed
Protein: Dopamine transporter
Description: Sodium-dependent dopamine transporter
Organism : Homo sapiens
Q01959 ENSG00000142319
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 11000-11000 - - -
Enzyme Hydrolase
- - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 39000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 3700-4300 - 2520-8160 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 114
Assay Description Organism Bioactivity Reference
Inhibition of human FAAH at 1 uM Homo sapiens -1.68 %
Inhibition of CYP3A4 at 10 uM None 10.0 %
Inhibition of CYP2D6 at 10 uM None 10.0 %
Inhibition of CYP3A4 at 10 uM None 10.0 %
Inhibition of CYP3A5 at 10 uM None 10.0 %
Inhibition of CYP2D6 at 10 uM None 10.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 113.68 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 95.61 %
Displacement of [3H]citalopram from Sprague-Dawley rat brain SERT at 100 uM after 60 mins by liquid scintillation counting analysis relative to control Rattus norvegicus 50.0 %
Displacement of [3H]nisoxetine from Sprague-Dawley rat brain NET at 100 uM after 180 mins by liquid scintillation counting analysis relative to control Rattus norvegicus 50.0 %
Binding affinity to wild type human SERT expressed in African green monkey COS7 cells assessed as inhibition of [3H]-serotonin uptake at 100 uM after 3 mins by beta-scintillation counting analysis relative to control Homo sapiens 50.0 %
Displacement of [3H]nisoxetine from NET in Sprague-Dawley rat frontal cortex membranes incubated for 180 mins at 100 uM by radioligand binding assay Rattus norvegicus 50.0 %
Displacement of [3H]citalopram from SERT in Sprague-Dawley rat brain stem membranes incubated for 60 mins at 100 uM by radioligand binding assay Rattus norvegicus 50.0 %
Displacement of [3H]WIN35,428 from wild type human DAT expressed in COS7 cell membranes incubated for >90 mins by radioligand binding assay Homo sapiens 927.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 3.29 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.2 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.6 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.07 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 6.81 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.96 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -0.59 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -0.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.998 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.13 %

Related Entries

Cross References

Resources Reference
ChEBI 77585
ChEMBL CHEMBL1373
DrugBank DB00745
DrugCentral 1826
FDA SRS R3UK8X3U3D
Human Metabolome Database HMDB0014883
Guide to Pharmacology 7555
KEGG D01832
PharmGKB PA450530
PubChem 4236
SureChEMBL SCHEMBL34488
ZINC ZINC03831139
CONTENTS