MODAFINIL

Search structure
Trade Names:
Synonyms:
Status: Approved (1998)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: N06BA07
UNII: R3UK8X3U3D

Structure
InChI Key YFGHCGITMMYXAQ-UHFFFAOYSA-N
Smile 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

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Dopamine transporter inhibitor DailyMed PubMed
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

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Attention Deficit Disorder with Hyperactivity 4 D001289 ClinicalTrials
Cocaine-Related Disorders 3 D019970 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Stroke 3 D020521 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Sleep Apnea, Obstructive 3 D020181 ClinicalTrials
Postpoliomyelitis Syndrome 3 D016262 ClinicalTrials
Sleep Wake Disorders 3 D012893 ClinicalTrials
Fatigue 3 D005221 ClinicalTrials
Depressive Disorder, Major 3 D003865 ClinicalTrials
Narcolepsy 3 D009290 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Amphetamine-Related Disorders 2 D019969 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Deglutition Disorders 2 D003680 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Tobacco Use Disorder 1 D014029 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Cognitive Dysfunction 1 D060825 ClinicalTrials
Hypotension, Orthostatic 1 D007024 ClinicalTrials
Sleep Initiation and Maintenance Disorders 1 D007319 ClinicalTrials
Psychotic Disorders 1 D011618 ClinicalTrials
Tinnitus 1 D014012 ClinicalTrials
Sleep Apnea Syndromes 1 D012891 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 23.0
Nervous system disorders Headache 17.0
Nervous system disorders Headache 14.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea 9.0
Gastrointestinal disorders Dry mouth 7.0
Gastrointestinal disorders Nausea 7.0
Nervous system disorders Insomnia 6.0
Gastrointestinal disorders Nausea 6.0
Cardiac disorders Dizziness 5.0
Nervous system disorders Insomnia 5.0
Psychiatric disorders Anxiety 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Diarrhoea 4.0
Gastrointestinal disorders Dry mouth 4.0
Nervous system disorders Insomnia 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Psychiatric disorders Depression 3.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain upper 2.0
General disorders and administration site conditions Asthenia 2.0
Psychiatric disorders Depression 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness
Gastrointestinal disorders Dry mouth 2.0
Gastrointestinal disorders Dyspepsia 2.0
General disorders and administration site conditions Fatigue 2.0
Nervous system disorders Headache 2.0
Cardiac disorders Palpitations 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Gastrointestinal disorders Abdominal pain upper
Nervous system disorders Agitation 1.0
Psychiatric disorders Anxiety
General disorders and administration site conditions Asthenia
Investigations Body temperature increased 1.0
Eye disorders Conjunctivitis 1.0
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Decreased appetite 1.0
Psychiatric disorders Depressed mood 1.0
Psychiatric disorders Depression
Psychiatric disorders Depression 1.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 1.0
Immune system disorders Dermatitis contact 1.0
Gastrointestinal disorders Diarrhoea 1.0
Nervous system disorders Disturbance in attention 1.0
Gastrointestinal disorders Dry mouth
Cardiac disorders Dyspnoea 1.0
General disorders and administration site conditions Fatigue
Investigations Gamma-glutamyltransferase increased 1.0
Nervous system disorders Headache 1.0
General disorders and administration site conditions Hyperhidrosis 1.0
General disorders and administration site conditions Influenza like illness 1.0
Nervous system disorders Insomnia
Nervous system disorders Migraine 1.0
Gastrointestinal disorders Nausea 1.0
Psychiatric disorders Nervousness 1.0
General disorders and administration site conditions Pain 1.0
Cardiac disorders Palpitations
Nervous system disorders Paraesthesia 1.0
Renal and urinary disorders Polyuria 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 1.0
Rhinitis seasonal 1.0
Eye disorders Seasonal allergy 1.0
Cardiac disorders Tachycardia 1.0
Psychiatric disorders Tension 1.0
General disorders and administration site conditions Thirst 1.0
Nervous system disorders Tremor 1.0
Investigations Urine output increased 1.0
Gastrointestinal disorders Vomiting 1.0
Musculoskeletal and connective tissue disorders Muscle twitching 0.7
Renal and urinary disorders Pollakiuria 0.7
Nervous system disorders Ataxia 0.3
Renal and urinary disorders Bladder pain 0.3
Cardiac disorders Cardiac arrest 0.3
Infections and infestations Cystitis 0.3
Renal and urinary disorders Cystitis noninfective 0.3
Psychiatric disorders Erectile dysfunction 0.3
Hearing impaired 0.3
Ear and labyrinth disorders Hyperacusis 0.3
Blood and lymphatic system disorders Leukocytosis 0.3
Nervous system disorders Muscular weakness 0.3
Musculoskeletal and connective tissue disorders Pain in jaw 0.3
Psychiatric disorders Personality disorder 0.3
Skin and subcutaneous tissue disorders Photosensitivity reaction 0.3

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
18.45
Psychiatric disorders
15.96
Nervous system disorders
15.72
Injury, poisoning and procedural complications
9.45
Gastrointestinal disorders
5.56
Cardiac disorders
3.82
Skin and subcutaneous tissue disorders
3.65
Musculoskeletal and connective tissue disorders
3.3
Respiratory, thoracic and mediastinal disorders
3.03
Vascular disorders
2.99
Investigations
2.67
Pregnancy, puerperium and perinatal conditions
2.19

Cross References

Resources Reference
CAS NUMBER 68693-11-8
ChEBI 77585
ChEMBL CHEMBL1373
DrugBank DB00745
DrugCentral 1826
EPA CompTox DTXSID0023329
FDA SRS R3UK8X3U3D
Human Metabolome Database HMDB0014883
Guide to Pharmacology 7555
KEGG D01832
PharmGKB PA450530
PubChem 4236
SureChEMBL SCHEMBL34488
ZINC ZINC03831139
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