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Compound Detail

CHEMBL1373

MODAFINIL
💊 Approved Drug
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💊 Approved Drug
NC(=O)C[S+]([O-])C(c1ccccc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1373
Name MODAFINIL
Phase Approved
Structure Type MOL
InChI Key YFGHCGITMMYXAQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

CEP 1538 CEP-1538 CRC-40476 CRL 40476 CRL-40476 DEP-1538 Modafinil Modafinil civ MODAFINIL COMPONENT OF THN-102 MODAFINIL COMPONENT OF THN102 Modafinilo Modaphonil +4 more
7
Targets
31
Activities
2
Assay Types
0
PK Parameters
20
Publications
16
Known Names
20
Indications
1
Mechanisms

Molecular Properties

273.4
MW (Da)
2.01
ALogP
2
HBA
1
HBD
66.2
PSA (Ų)
0.85
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1994

Extended Properties

Molecular Formula C15H15NO2S
MW 273.36
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.24

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine transporter inhibitor INHIBITOR Sodium-dependent dopamine transporter ✓ ✓

Indications

Attention Deficit Disorder with Hyperactivity Narcolepsy Narcolepsy Sleep Apnea, Obstructive Alzheimer Disease Brain Neoplasms Cocaine-Related Disorders Cocaine-Related Disorders Depressive Disorder, Major Fatigue Multiple Sclerosis Postpoliomyelitis Syndrome Sarcoma, Ewing Sleep Wake Disorders Stroke Alcoholism Amphetamine-Related Disorders Cognition Deglutition Disorders Depressive Disorder

ATC Classification

N06BA07
modafinil
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 18 meas. best 6.03
IC50 13 meas. best 5.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.03 5.594 927.0 5
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.74 5.34 1832.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.6 5.4475 2520.0 8
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 5.43 5.406 3700.0 5
Unchecked
CHEMBL612545
 Ki 5.03 5.03 9250.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.96 4.96 11000.0 3
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 4.5 4.5 31300.0 2
D(3) dopamine receptor
CHEMBL234
 Ki 4.41 4.41 39000.0 1
Transporter
CHEMBL6184
 IC50 4.19 4.19 63900.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 927.0 nM 6.03 Displacement of [3H]WIN35,428 from wild type human DAT expressed in COS7 cell me... 27933960
Sodium-dependent dopamine transporter Ki = 1456.0 nM 5.84 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter IC50 = 1832.0 nM 5.74 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter Ki = 2000.0 nM 5.7 Binding affinity to DAT (unknown origin) 27933960
Sodium-dependent dopamine transporter Ki = 2520.0 nM 5.6 Dopamine Transporter Binding Assay: Dopamine Transporter Binding Assay. Brains f... -
Sodium-dependent dopamine transporter Ki = 2520.0 nM 5.6 Binding Assay: Dopamine Transporter Binding Assay. Brains from male Sprague-Dawl... -
Sodium-dependent dopamine transporter Ki = 2520.0 nM 5.6 Dopamine Transporter Binding Assay: Brains from male Sprague-Dawley rats weighin... -
Sodium-dependent dopamine transporter Ki = 2520.0 nM 5.6 Displacement of [3H]WIN35428 from DAT in Sprague-Dawley rat brain membranes 21344069
Sodium-dependent dopamine transporter Ki = 2600.0 nM 5.58 Displacement of [3H]WIN35,428 from Sprague-Dawley rat brain DAT after 120 mins b... 24494745
Sodium-dependent dopamine transporter Ki = 3090.0 nM 5.51 Binding affinity to human DAT A480T mutant expressed in African green monkey COS... 24494745
Sodium-dependent dopamine transporter IC50 = 3700.0 nM 5.43 Inhibition of rat DAT 22264475
Sodium-dependent dopamine transporter IC50 = 3700.0 nM 5.43 Inhibition of rat DAT 22749190
Sodium-dependent dopamine transporter IC50 = 3700.0 nM 5.43 Displacement of 3H-WIN-35428 from DAT in rat striata after 120 mins 22546675
Sodium-dependent dopamine transporter Ki = 3800.0 nM 5.42 Inhibition of high affinity uptake by the dopamine transporter from rat synaptos... 15537337
Sodium-dependent dopamine transporter IC50 = 4300.0 nM 5.37 Inhibition of rat DAT-mediated dopamine reuptake 22749190
Sodium-dependent dopamine transporter IC50 = 4300.0 nM 5.37 Inhibition of rat DAT-mediated dopamine reuptake 22264475
Sodium-dependent dopamine transporter Ki = 8160.0 nM 5.09 Displacement of [3H]WIN35428 from DAT in Sprague-Dawley rat striatum membranes i... 31661268
Sodium-dependent dopamine transporter Ki = 8160.0 nM 5.09 Displacement of [3H]WIN35428 from DAT in Sprague-Dawley rat striatal membranes i... 32947229
Unchecked Ki = 9250.0 nM 5.03 Displacement of [3H]WIN35,428 from human DAT Y156F mutant expressed in COS7 cell... 27933960
Cytochrome P450 2C19 IC50 = 11000.0 nM 4.96 Inhibition of CYP2C19 22749190

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 432
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
17640897 10.1073/pnas.0705087104 Thalamocortex 12
17640897 10.1073/pnas.0705087104 Cortex 8
17640897 10.1073/pnas.0705087104 Unchecked 6
27933960 10.1021/acs.jmedchem.6b01373 Unchecked 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
24494745 10.1021/jm401754x Sodium-dependent serotonin transporter 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
24494745 10.1021/jm401754x Sodium-dependent dopamine transporter 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
18954992 10.1016/j.bmc.2008.10.027 Cortex 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
32947229 10.1016/j.ejmech.2020.112674 Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine